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Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode

May 22, 2019 / 48:06

This episode covers unsolved mysteries including the disappearance of Debbie Wolfe, the search for Kandra Dena Olson, and the fate of pilot Jeffrey Sullivan. Family members and investigators share their experiences and theories surrounding these cases.

Debbie Wolfe, a nurse from Fayetteville, North Carolina, went missing on December 26, 1985. Her body was found in a pond, but her family believes she was murdered due to inconsistencies in the investigation and evidence of foul play.

Kandra Dena Olson vanished in the early 1900s, and her granddaughter Geneva Fox has been searching for answers. Geneva's investigation leads her to an unmarked grave in Ellis, Missouri, which may be connected to her grandmother's disappearance.

The episode also discusses Jeffrey Sullivan, a former Air Force pilot who disappeared during a covert mission in 1963. His daughter Sherry Sullivan has spent years trying to uncover the truth about her father's fate, suspecting he may have been imprisoned in Cuba.

Viewers are encouraged to help solve these mysteries by providing any information they may have.

TL;DR

This episode investigates the mysterious disappearances of Debbie Wolfe, Kandra Dena Olson, and Jeffrey Sullivan, highlighting family searches and inconsistencies in investigations.

Episode

48:06
00:00:03
this program is about unsolved mysteries
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whenever possible the actual family
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members and police officials have
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participated in recreating the events
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what you are about to see is not a news
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broadcast
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Christmas Day 1985 a relaxed joyful
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holiday for 28 year-old Debbie wolf
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hunter family 7 days later Debbie's body
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was found submerged in an oil can a pond
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behind her home police say she drowned
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accidentally her mother says it was
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murder 80 years ago the young mother
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Conrad ena Olson boarded a train and
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booked field Wisconsin and vanished
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now Conrad Ines grandpa has uncovered a
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string of bizarre clues leading to an
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unmarked grave and more unanswered
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questions 1959 Fidel Castro seizes power
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in Cuba four years later former Air
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Force pilot Jeffrey Sullivan undertakes
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a clandestine mission with anti-castro
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forces and disappears somewhere over the
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Caribbean Sea Sullivan's daughter has
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uncovered evidence that her father may
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have been imprisoned in Cuba also
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tonight we'll update our reach the story
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of a daring prison escape bikes to our
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viewers a female prison gardener
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jailhouse lover were tracked down to a
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motel in Canada and captured jointly you
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may be able to help solve a mystery
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[Music]
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[Applause]
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[Music]
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when Debbie wolf a 28 year old nurse
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from Fayetteville North Carolina
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disappeared her family became
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understandably concerned it began as a
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tragic but uncomplicated missing-persons
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case but a number of unanswered
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questions hinted at a darker secret for
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Debbie's family and friends a police
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investigation appeared flawed Debbie
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thought that helping people was the best
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thing in the world she could do
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she thought that if she could be a nurse
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and she could pay back some of the
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kindness and some of the consideration
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that had been given to her during her
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short lifetime that maybe she would make
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her own market and I think she did on
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Wednesday December 25th 1985 Debbie
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celebrated a typical family Christmas at
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her mother's home a day devoted to close
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friends and goodwill
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[Music]
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or p.m. the day after Christmas upon
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completing her shift at the hospital
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Debbie wolf left work presumably heading
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home the next morning Debbie should have
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been at work she had to be at work at
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8:00 Debbie did not go to work
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Debbie did not answer her telephone it
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wasn't like Debbie at all she never
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missed work she would call in if she was
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even going to be a few minutes late she
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would call in let them know but they had
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had no word from Debbie and I had had no
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word from Debbie December 27th a day
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after Debbie disappeared Jenny Edwards
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drove to Debbie's home with her husband
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John and a family friend Kevin Gorton
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Debbie lived in an isolated cabin 7
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miles outside of Fayetteville because
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Debbie was unusually neat and meticulous
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they were surprised by what they found
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in and around the cabin that seats
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pushed way back Debbie's car was not
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hard to wear she always parked we looked
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around and we saw beer cans laying in
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the yard and it was definitely a brand
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of beer that Debbie did not dream
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her dogs were running loose as they
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normally did but they had not been fed
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Debbie Debbie are you home
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there were small things that were out of
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place that Debbie would not have put
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where they were placed there was a
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uniform laying on the floor in the
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kitchen things thrown in in the kitchen
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on the floor like maybe she took them
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off it's a uniform John yeah John Kevin
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Gordon found Debbie's purse shoved back
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under her bed hey guys I think I found
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Davey's purse
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found what
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then here work today
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there was also an odd message on
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Debbie's answering machine recorded
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earlier that day before Jenny arrived
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you've been out a lot of days making it
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worried when you meant another one just
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want to make sure you're okay
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what concerned me about his message was
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that he said that she had missed a lot
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of days at work and she hadn't in fact
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she had only missed a few hours at work
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at the time that he put the message on
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the answering machine
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fifty feet from the cabin was a pond
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they searched the entire area and found
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no trace of Debbie
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Jenny Edwards call the Sheriff's Office
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she was told that law enforcement would
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become involved only after 72 hours had
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elapsed from the time of the
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disappearance on Tuesday December 31st
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the Sheriff's Department finally
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conducted a full-scale search five days
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after Debbie had last been seen they
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searched the cabin later that afternoon
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they brought the bloodhounds out which
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they could find nothing at all they then
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walked around the edge of the pond I was
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there for that and they looked across it
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granted it's a small pond but it's deep
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in some places and it's not that small I
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asked if they were going to put a boat
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into the water and at least a paddle
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across it they said they didn't know it
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was getting too late and that they would
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let me know the next day of course some
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of the individuals there that had that
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were friends other family had been there
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a couple days prior had done some
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searching on their own and I think it
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was mentioned that they had already
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looked in the pond there was no use for
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us to look in the pond so I don't think
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we did a dive of the pond or a complete
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search of the pond on that day no we did
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not
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at that time I asked him if it would be
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all right then if I got my own divers to
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go into the pond and he said certainly
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New Year's Day 1986 Debbie Wolfe had now
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been missing for six days
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Kevin Gorton had another friend Gordon
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Childers returned to the pond
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both men were familiar with rescue work
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Gordon dragged the pond looking for
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evidence
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he was in the water approximately two
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minutes when he called out to me and
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told me that he had found what looked
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like a set of footprints in the drag
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mark um as he continued to zigzag back
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and forth across the pond
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he continued to come over these tracks
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two sets of footprints were found along
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with the drag marks these prints
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remained in the mud for weeks I went out
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and went under and following the trails
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maybe six inches from the bottom and
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just kind of like coasting along the
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bottom after no good hard kid I hit
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something my mask flooded
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[Music]
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looks like a body down here are you sure
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let me double check so I went back down
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confirmed the whole spent more time
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looking didn't touch or disturb anything
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I couldn't see above mid-drift is as in
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Saba look like a burn barrel there's a
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rusty 55-gallon oil drum type thing with
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holes in
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the police were called to the scene
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a dead woman was identified as Debbie
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wolf an autopsy revealed no trace of
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drugs or alcohol and Debbie's system
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there were no obvious signs of foul play
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the corner rule the cause of death is
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drowning but was unable to determine
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exactly when Debbie had died a number of
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discrepancies soon surfaced which led
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Debbie's family and friends to believe
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Debbie had not drowned and Claude state
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just a fight for life which was quite on
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contrary wait Debbie was the eyes were
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closed the mouth was closed arms were a
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relaxed state just her whole body was
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relaxed she looked like she was asleep
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we theorized that if it was an
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accidental drowning that at that point
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she may have been out around the pond
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her dogs were running loose when the
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family members and the Sheriff's
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Department personnel were there possibly
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she was playing with the dolls and fell
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in another thing that struck me funny
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was the fact that Debbie was was clean
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the clothes were clean you know her face
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was not carrying a lot of silt the day
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that me and Gordie went into the water
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and spent maybe 20 minutes it took us
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both about three days to watch her wash
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her dive suits out from just the
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accumulation of the silt and mud that
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was in the bottom of that pond
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police also began to deny that the body
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had been found inside of a barrel after
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the body was retrieved and dispatched to
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a local hospital I walked away from the
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pond up to the cabin as I was walking
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away they were discussing how to mark
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the barrel and how to bring it out then
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I thought surely they would do that I
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walked back out of the cabin about ten
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minutes later and saw all their cars
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leaving and I asked one of our friends
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who were there I said
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what happened do they have the barrel
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and they said no they decided to leave
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it there they'll get it in the morning
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the next day they went back to get the
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barrel it seems that the barrel was gone
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all of a sudden it didn't exist the same
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barrel that had been there the night
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before
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in my opinion and opinions of some of
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the investigators what appeared to be a
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barrel to some of the divers could have
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been the field jacket which may have
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ballooned out as she was laying at that
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angle at the bottom of the pond there
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was never a barrel touched by any of the
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divers according to their statements
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most definitely bout none of our divers
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than we ever touch a barrel there was no
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doubt my mind her purse had positive
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that it was an old burn barrel or
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something about nature you know metal
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rusted 55-gallon type drum and that the
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body was in I remembered the barrel that
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was sitting by Debbie's cabin this is
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known here as an oil barrel it's a big
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round metal drum farmers use it for
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burning trash however she didn't use it
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for that instead we used it for target
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practice when we were out there shooting
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pistols when after I had called law
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enforcement that we had located a party
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I went over to the spot where the barrel
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was and the barrel was gone
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the indention of the barrel was still
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their own on the ground but the barrel
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was no longer there
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a few months later
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Jenny discovered another inconsistency
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when I got a chance to examine the
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clothes that were owned Debbie's body I
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looked at them very carefully and
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realized that those were not Debbie's
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clothes the pants were very very much
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too long for Debbie the Field Jacket
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Debbie had owned a field jacket that had
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belonged to her brother and that is a
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totally different field jacket than what
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was found on the body the bra was cup
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sized three sizes too large for her and
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around size it would be two sizes too
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large for her the shoes
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Debbie wore a ladies size seven and
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these were a men's size six which winds
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up being about three sizes larger I
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don't know why clothing belonging to
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Debbie or what didn't blown today of
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course my mother would probably know
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that information or have that
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information know more about what blown
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to hurt him then we would of course
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investigators all we do is ask questions
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and and try to get some answers we do
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know for a fact through our
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investigation that the tennis shoes she
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had on were her tennis shoes we have
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photographs of them of her with those
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tennis shoes on prior to her death
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that's much no want comment on the club
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Jennie Edwards became convinced that
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Debbie had been murdered
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I owe you today among her duties at work
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Debbie was assigned to coordinating the
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hospital volunteers
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I don't want to go out with you I've
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told you I volunteer in particular seem
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to bother her quite a bit because he had
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a history of psychiatric illnesses wait
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[Music]
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according to Jenny the volunteer
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obtained Debbie's home phone number
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hello it's me look I told you I don't
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want you calling me here anymore you
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don't even know where I live look I was
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investigated you I did sure the night
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that the body was brought to the surface
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however he provided an alibi and refused
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to take a polygraph
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so he wasn't questioned any longer he
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left several days after that to go out
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of state
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the second man suspected by Jenny
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Edwards was also a hospital volunteer he
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did there was another volunteer at the
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hospital at the same time that wanted to
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become romantically involved with Debbie
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Debbie discusses with everyone including
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him and told him that she would be his
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friend but nothing else she was
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interested in someone else totally away
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from the hospital you know I've got a
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boyfriend jenny is convinced that this
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was the man who called Debbie the day
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after she disappeared expressing concern
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that she'd been missing from work for
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day
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you've been out a lot of days make me
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worry the second suspect was also
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questioned by police
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anyone family requested that we talk to
00:15:54
our interview we tried to interview of
00:15:57
course through the information we
00:15:59
received 30 in these interviews there
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was nothing there that we could use in
00:16:07
any criminal prosecution or there was
00:16:11
nothing there at the indicate to us that
00:16:14
this was a homicide what really happened
00:16:18
to Debbie wolf her mother believes she
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was taken hostage by one of the two
00:16:22
suspects kept alive for several days and
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finally killed
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later she believes someone returned to
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the pond to remove the barrels so the
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ruling of foul play would be dismissed
00:16:41
there are people out there who know what
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happened to Debbie they know who's
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responsible and I'm hoping that they
00:16:49
will come forward and finally say
00:16:51
something
00:16:53
Debbie was a lovely person and she was
00:16:56
loved by very very many people and I
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think that she has a right to be put to
00:17:05
rest
00:17:06
finally and I'd like to do that next our
00:17:13
viewer tips in Canada led to the capture
00:17:15
of a woman who allegedly helped her
00:17:17
lover escape from prison
00:17:21
[Music]
00:17:26
last month we profiled the case of a
00:17:28
corrections officer from Maryland whose
00:17:30
secret love affair with a prison inmate
00:17:32
changed her from a devoted mother into a
00:17:34
wanted fugitive on the run tonight a
00:17:37
dramatic update to the story
00:17:40
for ten years 46 year-old Sandra Kay
00:17:43
Beeman worked as a prison matron at a
00:17:45
maximum security facility in Cumberland
00:17:48
Maryland 30 year old Edgar Kearns is
00:17:52
being held at the Cumberland prison will
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awaiting sentencing on charges of check
00:17:56
fraud on August 29th late 290 head ger
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Kearns and another inmate
00:18:03
James Barr has made a daring escape it
00:18:07
appeared that they had taken Kate Beaton
00:18:09
hostage authorities were shocked when
00:18:13
they later learned that Kate demon had
00:18:15
actually helped through the escape and
00:18:16
that she was in love Edgar Kearns
00:18:19
I guess you maybe fall in love with
00:18:25
somebody and do some strange things but
00:18:29
caves pretty well lost about everything
00:18:31
that she ever had over this one incident
00:18:36
up to attack just six hours after our on
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Twitter
00:18:40
Sandra key be led returns were captured
00:18:42
in Canada on September 10th place after
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the escaped demon and currents checked
00:18:50
into the beach motor motel in Hamilton
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Canada they registered as husband and
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wife under the assumed names Fred and
00:18:57
Sandy Smith I was watching TV and all of
00:19:01
a sudden this lady's picture come on so
00:19:06
I called my wife and she was over the
00:19:08
kitchen ironing and I said do you
00:19:10
recognize this lady and she said yes
00:19:12
she's the lady that's living in room 12
00:19:15
and by this time the gentlemen come on
00:19:18
and I said oh he also lives in there so
00:19:22
I reached over immediately and picked up
00:19:25
the phone and call the police
00:19:26
when we got to the beach Motor Hotel the
00:19:30
information from the Mitchells was the
00:19:32
effect that they hadn't left the room
00:19:34
and it wasn't their policy to leave the
00:19:36
room during the evening we were
00:19:38
convinced they were still inside the
00:19:40
room the officers of the emergency
00:19:42
response unit which is equivalent to the
00:19:45
SWAT team forced the door open and
00:19:48
almost found to be they could
00:19:51
a witness later told authorities that he
00:19:53
had seen the fugitive couple getting
00:19:55
into a taxi cab earlier that evening we
00:19:59
were able to determine the name of the
00:20:01
cab and a check with a cab company
00:20:04
revealed the driver I think about the
00:20:06
beach trip and that just up from the
00:20:09
motel and they I asked him where they
00:20:12
were going and they said the red rose
00:20:14
motel when we got to the motel the cab
00:20:18
driver said he had taken one of our
00:20:21
officers was able to determine from the
00:20:23
office register at that location that
00:20:26
they had in fact booked in and that
00:20:27
currents in fact that uses bright name
00:20:31
humorously
00:20:33
the emergency response unit we did three
00:20:38
or four officers of the emergency
00:20:40
response and approached the front door
00:20:42
the motel room it was at that point that
00:20:45
someone from the inside of the room
00:20:47
looked out through the drapes
00:20:49
the officers been forced open the door
00:20:52
entered the room turns he was forced to
00:20:57
the floor the motel room and held in a
00:21:00
position of safety the female in the
00:21:03
room was in the bed and her hands were
00:21:05
handcuffed above her head to the head at
00:21:09
that point they're both persons were
00:21:10
arrested Kearns was removed by my
00:21:13
partner myself and transported to
00:21:15
Central Station
00:21:18
we wanted to know how we had learned of
00:21:21
his wearables we asked him if he had
00:21:24
ever seen the program before he said yes
00:21:27
he had you told him that he was on it
00:21:30
tonight he was astounded on October 30th
00:21:36
1990s and rock a demon and Edgar Kern's
00:21:38
were returned to Maryland
00:21:40
[Music]
00:22:01
next a woman's search for her missing
00:22:04
grandma collides with a mysterious
00:22:05
legend of murder
00:22:09
[Music]
00:22:18
amid the windswept prairie near the
00:22:20
small town of Ellis Missouri lays a
00:22:22
lonely unmarked grave
00:22:27
legend has it as a resting place of an
00:22:30
unknown woman found murdered near the
00:22:31
railroad tracks years ago
00:22:36
for as long as anyone can remember the
00:22:39
grave has been maintained by railroad
00:22:41
workers adorned with flowers every
00:22:43
Memorial Day in the past three years
00:22:49
here featured many stories of lost loves
00:22:52
our next story also concerns a missing
00:22:55
loved one but with an odd twist the
00:22:57
woman disappeared 80 years ago this is a
00:23:00
story of a granddaughters relentless
00:23:02
search that has brought her face to face
00:23:03
with a mysterious legend our murder in a
00:23:06
small town and dark family secrets kept
00:23:08
hushed for nearly a hundred years
00:23:13
Brookfield Wisconsin the early 1900s
00:23:17
thirty-eight-year-old con Rodina Olson
00:23:19
said goodbye to her four children
00:23:24
thank you guys I'll see you tomorrow she
00:23:28
told him she was going to Milwaukee for
00:23:29
a doctor something he would return the
00:23:31
following day no I'd rather stay here to
00:23:40
fight you
00:23:42
[Music]
00:23:47
Kandra Dina Olsen's family never saw her
00:23:50
again
00:23:51
[Music]
00:23:54
for the rest of his life Kandra Dena's
00:23:56
eldest son had one regret not getting on
00:23:59
the train that morning he felt that if
00:24:02
he had went with her she would have been
00:24:04
back she would have come back to them my
00:24:08
father he suffered for this all of his
00:24:11
life he couldn't accept why and how she
00:24:15
went away he never knew why she went
00:24:18
away and didn't come back in 1983 Geneva
00:24:24
Fox er began investigating her
00:24:25
grandmother's disappearance hoping to
00:24:28
find answers to the questions that
00:24:29
haunted her father his entire life she
00:24:33
learned that in 1891 20 year-old Conrad
00:24:36
ena Heitmann married thirty year old
00:24:38
Karl Olson a railroad coachman
00:24:40
by all accounts Carlin Cardenas marriage
00:24:43
was not a happy
00:24:49
and all of my research I found out that
00:24:52
my grandfather was I don't know if he
00:24:55
was abusive physically to my grandmother
00:24:58
but I did understand that he was not
00:25:02
good to hurt
00:25:07
the back in those days when there was a
00:25:09
bad marriage people didn't get a divorce
00:25:13
one of one of the people just walked
00:25:16
away from the marriage and this this is
00:25:19
actually what I had thought for many
00:25:21
years that had happened to her but now I
00:25:24
don't I feel she was taken something bad
00:25:29
had to happen to her
00:25:32
in September of 1985 while working at
00:25:36
her gift shop on South Sioux City
00:25:37
Nebraska Geneva had a bizarre encounter
00:25:40
with one of her customers
00:25:41
Alice chance meeting as startling
00:25:44
possibility began to emerge this was a
00:25:48
quiet day and all I suppose around noon
00:25:51
this lady come into my store I knew
00:25:54
there was something different but I
00:25:57
couldn't grasp what it was and she
00:25:59
walked around a bit I I usually let
00:26:01
people walk around my store so I don't
00:26:03
you know I don't bug
00:26:06
[Music]
00:26:07
and so she come up around counter and we
00:26:12
got to talking and she told me her name
00:26:14
was Susanna I'm looking for a Pegasus
00:26:16
Pegasus and she says well I'm a psychic
00:26:18
well no I'm a psychic and just out of a
00:26:23
clear blue sky she said you want to ask
00:26:24
me about your grandmother don't you and
00:26:27
I was amazed I said yes and she said do
00:26:31
you have anything of your grandmother's
00:26:32
here nice and yes I said I have a
00:26:34
marriage license and I said I have their
00:26:36
wedding picture and she closed her eyes
00:26:37
and she says not only talk be very quiet
00:26:41
in then all of a sudden she said I can
00:26:44
see her boarding a train
00:26:45
I can see children crying I can see her
00:26:48
being beaten and I feel that your
00:26:51
grandfather knows what happened to her
00:26:55
it's just kind of sent shivers down my
00:26:58
spine I I was flabbergasted I thought I
00:27:04
don't believe this how could she know
00:27:05
how could how could she know this about
00:27:08
my grandmother later
00:27:11
Susanna's office Geneva was given more
00:27:13
possible clues about her grandmother's
00:27:16
disappearance Susannah to Geneva that
00:27:20
she would soon be receiving a packet of
00:27:22
old letters the letters would pinpoint
00:27:24
the year the Geneva's grandmother
00:27:26
disappeared Ellis has something to do
00:27:30
about where she is at this point she
00:27:33
also told you neva that the name Ellis
00:27:35
was somehow connected to the
00:27:36
disappearance and that her grandmother
00:27:38
was buried in an unmarked grave
00:27:41
and she says also I see within a year's
00:27:45
time you will be getting a letter from
00:27:48
an unknown source yet not heard from
00:27:50
somebody you don't even know of that is
00:27:53
going to tell you where this greatest in
00:27:56
cutter several weeks later Susanna's
00:27:59
first predictions seem to come true
00:28:04
within two months time I did get a
00:28:07
packet of letters and pictures also
00:28:10
there was many of them from eighteen and
00:28:15
eighteen hundreds
00:28:16
and within these old letters it states
00:28:21
there was some dissension in the
00:28:22
marriage and it also states that she
00:28:25
that the last known from heard from her
00:28:28
it was around 1910 encouraged by this
00:28:32
new information Geneva sent a letter
00:28:34
detailing her search to a Midwestern
00:28:36
newspaper the editors found the story
00:28:39
interesting and printed the letter I got
00:28:42
in contact with Geneva when I read a
00:28:45
piece and in a monthly magazine that she
00:28:49
was looking for her grandmother bill
00:28:53
carpenter route to Geneva and told her
00:28:55
of the unmarked grave near Ellis
00:28:57
Missouri
00:28:58
he says there's quite a story about this
00:29:01
death and he says it is an unmarked
00:29:03
grave in its in its along the railroad
00:29:05
right away and when he said it's along
00:29:08
the railroad right away I couldn't
00:29:10
believe it I just tears come to my eyes
00:29:12
I just wanted to cry you know this was
00:29:15
another prediction of Susanna's that
00:29:17
came true
00:29:19
at the turn of the century Ellis
00:29:21
Missouri was a small farming town
00:29:23
according to local legend fashionably
00:29:26
dressed woman got off the train at Ellis
00:29:31
she was seen arguing with a man
00:29:33
witnesses reported that it appeared to
00:29:35
be a lover's quarrel with a couple storm
00:29:38
east down the tracks a man was later
00:29:42
seen returning to the station of law he
00:29:45
boarded another train and left town
00:29:48
three days later the woman's body was
00:29:50
discovered alongside the train tracks
00:29:52
she had been murdered there was nothing
00:29:56
to identify the woman reveal where she
00:29:58
had come from
00:30:02
according to the legend railroad workers
00:30:05
buried the woman in a field a few yards
00:30:07
from where she was found
00:30:10
I want to think this is my grandmother's
00:30:12
grave in my heart I think it is and I
00:30:18
don't know what else could have happened
00:30:19
to my grandmother I think with all my
00:30:20
research I would have found out
00:30:22
something anything but this is what it
00:30:25
has led to and all of these predictions
00:30:27
have all all come here they've all how
00:30:29
could this not be my grandmother I
00:30:32
certainly wish her well in finding her
00:30:34
grandmother but I remain rather
00:30:36
skeptical about the story because the
00:30:38
fact that that we have newspaper
00:30:40
articles about the unknown grave
00:30:42
dating from before 1910 when her
00:30:44
grandmother apparently disappeared this
00:30:47
newspaper article does seem to discount
00:30:49
Geneva's conclusion it was published in
00:30:52
1888 22 years before Conrad ina Olsen
00:30:55
disappeared it describes a dead woman as
00:30:58
being less than 20 years old
00:31:00
Conrad ena Olsen was 38 when she
00:31:03
vanished 40 years ago I talked to an 85
00:31:08
year old man that had worked for the
00:31:10
railroad all of his life and he said
00:31:15
that the lady that they found along the
00:31:18
tracks was approximately in her 30s I
00:31:22
feel it is her grandmother that's my
00:31:26
feeling if the woman found murdered
00:31:28
alongside the railroad tracks was Conrad
00:31:31
ena Wilson then who was the man seen
00:31:34
arguing with her at the Ellis train
00:31:36
station at the time my grandmother
00:31:38
disappeared I've always heard the story
00:31:41
that my grandfather also went away for a
00:31:43
period of time I don't want to believe
00:31:45
that my grandfather did
00:31:47
with her I don't believe he did I don't
00:31:49
want to believe it but the way this is
00:31:53
all coming about I don't know what to
00:31:56
think about it
00:31:58
until I find for sure this is my
00:32:01
grandmother I will always have that
00:32:03
doubt of not knowing and I want to know
00:32:06
not only for myself but for my father
00:32:12
I'm gonna find her I feel that there's
00:32:14
somebody out there that knows what
00:32:16
happened to her
00:32:16
and I I just wanna know when we return
00:32:23
the disappearance of an American pilot
00:32:26
apparently on an anti-castro mission in
00:32:28
Latin America
00:32:29
one eyewitness claims he was imprisoned
00:32:31
in Cuba
00:32:35
[Music]
00:32:45
September 23rd 1963 Waterbury
00:32:48
Connecticut 28 year old Jeffrey Sullivan
00:32:52
a former Air Force pilot prepared to
00:32:55
depart on a mysterious covert mission
00:33:00
the way my mom relates it and my father
00:33:03
I was supposed to come back in five days
00:33:05
[Music]
00:33:07
give you a call as soon as I get a
00:33:09
chance to I don't know if he was nervous
00:33:11
but he gave her his Saint Christopher
00:33:14
medal which he wore all the times he
00:33:17
explained to her that this would be his
00:33:20
last trip yes you do and not because he
00:33:25
wasn't coming back but because he didn't
00:33:27
want to be involved in this type of
00:33:28
operation anymore
00:33:33
he took off that morning and that was
00:33:36
the last time she ever saw
00:33:38
[Music]
00:33:42
four days later Jeffry Sullivan
00:33:44
disappeared over the Caribbean the
00:33:47
mystery of what happened during those
00:33:48
four days still haunts his daughter
00:33:54
sherry Sullivan was seven years old when
00:33:57
she lost her father today Sherry's a
00:34:00
private investigator living in Bangor
00:34:02
Maine for the past six years she is
00:34:05
sifted through a labyrinth of
00:34:06
bureaucratic red tape and false leads
00:34:08
hoping to uncover the truth of her
00:34:10
father's fate no one wanted to say he
00:34:14
wasn't coming back as it rolled into the
00:34:19
years it was a kind of thing that just
00:34:20
wasn't talked about I mean no one knew
00:34:22
what to say and none of us were ever
00:34:25
allowed to go through a grieving process
00:34:27
because as far as we were concerned he
00:34:29
wasn't dead
00:34:33
Jeffrey Sullivan enlisted in the Air
00:34:35
Force when he was 18 in 1957 he earned
00:34:38
his wings
00:34:39
two years later Sullivan receives an
00:34:42
honorable discharge and became a
00:34:44
freelance commercial pilot the same year
00:34:50
Bedell Castro's revolution triumphed in
00:34:52
Cuba
00:34:53
the communist threat was now only 90
00:34:55
miles from American shores almost
00:34:58
overnight both US government backed and
00:35:01
independent covert operations were
00:35:02
launched to undermine Castro's regime
00:35:08
one of the men involved in these
00:35:10
operations was 37 year-old Alex Roarke a
00:35:13
journalist and photographer from New
00:35:14
York by writing a series of articles
00:35:17
about Cuban exiles walk became active in
00:35:20
the campaign to overthrow Castro's new
00:35:22
government Jeffrey in 1961 Jeffery
00:35:32
Sullivan and Alex Roth met work soon
00:35:36
hired Sullivan as a pilot for his plan
00:35:38
destined anti-castro activities when
00:35:42
Jeffrey Sullivan shook hands with Alex
00:35:44
Roark he sealed his own fate after the
00:35:47
Cuban Revolution a staggering array of
00:35:49
anti-castro operations sprung up in the
00:35:51
United States many of them were
00:35:53
organized by shadowy characters it was a
00:35:56
murky underworld of these clandestine
00:35:58
operations in which Jeffrey Sullivan
00:36:00
became caught up March 1961 us-backed
00:36:08
human exiles prepared to invade Cuba the
00:36:10
Bay of Pigs
00:36:12
on April 17 they were defeated in less
00:36:15
than a day because the US government
00:36:16
failed to supply air support in October
00:36:21
of 1962 Soviet missile silos were
00:36:23
discovered in Cuba for seven days the
00:36:26
world was on the brink of nuclear war
00:36:31
after the missile crises operations
00:36:34
against Cuba were still carried on by
00:36:36
the US government but they were trying
00:36:39
to be more discreet about it and they
00:36:42
did shed some of the more loose canon
00:36:46
operations and I think Alex Rourke's
00:36:49
could have been classified as such there
00:36:52
was a public order to men like Alexander
00:36:56
Rourke and Geoffrey Sullivan to stop
00:36:59
their operations against Cuba altogether
00:37:06
on September 23rd 1963 eight days after
00:37:10
the official warning was issued Geoffrey
00:37:12
Sullivan left Waterbury Connecticut the
00:37:15
next day he resurfaced in Fort
00:37:17
Lauderdale Florida with Alex Rourke
00:37:20
[Music]
00:37:23
in Fort Lauderdale Sullivan and Rock met
00:37:25
with two men one of them was Frank
00:37:27
Sturgis who had also been named in the
00:37:29
public warning years later Sturgis had
00:37:32
become well known for his role in the
00:37:34
Watergate scandal crook told me he did
00:37:38
buy a b-25 bomber and he wanted to take
00:37:42
to be 25 to Nica Raja wanted to sit down
00:37:47
and talk with general samosa in order to
00:37:50
have a base of operations in Nicaragua
00:37:53
and to as the general to fit out the b25
00:37:57
for bombing missions inside of Cuba I'll
00:38:00
need to see your Sturgis convinced wrong
00:38:02
that they should first meet personally
00:38:03
with Nicaraguan officials the floor men
00:38:06
rented an airplane and agreed to depart
00:38:08
for Nicaragua the following morning the
00:38:15
next day
00:38:15
Rourke's wife drove him to opal acha
00:38:17
Airport in Fort Lauderdale on the way
00:38:24
they picked up another man mrs. rora
00:38:28
didn't know who this gentleman was he
00:38:31
spoke broken English but she drove the
00:38:34
both of them to the airport where my
00:38:36
father was and dropped them off
00:38:39
at approximately 8 a.m. the santa lair
00:38:42
twin-engine plane took off from Fort
00:38:44
Lauderdale on board were Jeffrey
00:38:47
Sullivan Alex Roark and the stranger
00:38:50
curiously Frank Sturgis and his
00:38:52
associate were left behind what
00:38:56
transpired during the next 48 hours
00:38:58
remains a jumbled maze of unanswered
00:39:00
questions
00:39:01
[Music]
00:39:04
according to the official FAA report
00:39:07
Sullivan's flight activities were highly
00:39:09
unusual
00:39:10
he returned to Fort Lauderdale three
00:39:13
times with very little explanation
00:39:16
on his third return to the airport the
00:39:18
planes landing gear remain retracted all
00:39:21
on your landing gear appear to be up
00:39:22
side steps into riding over it Sullivan
00:39:28
did not attempt to land at Fort
00:39:30
Lauderdale again five hours later he
00:39:37
arrived at North Perry Airport just 30
00:39:39
miles away the plane made a short puddle
00:39:44
hop over to Hollywood Florida which is a
00:39:47
very short distance away and told the
00:39:51
people there to refuel right and the an
00:39:56
operator the Flying Service said that it
00:39:59
hardly took any gasoline to refuel it
00:40:02
what should have been a 20-minute flight
00:40:04
had taken nearly five hours no one knows
00:40:08
where the plane was during that time
00:40:15
at 1:30 p.m. Sullivan and his companions
00:40:18
departed north Perry the official flight
00:40:21
plan was to Tegucigalpa Honduras as
00:40:24
their final destination
00:40:29
Sullivan next contacted the tower at
00:40:32
Miami International Airport at 3:43 p.m.
00:40:36
he filed a revised flight plan listing
00:40:38
to command Panama's his destination
00:40:40
[Music]
00:40:44
Sullivan attempted to file a flight plan
00:40:46
for a destination that was some two
00:40:49
hours beyond the normal range of his
00:40:50
aircraft when he was informed of this by
00:40:54
the air traffic controller on duty he
00:40:57
then changed his destination from
00:41:00
however this destination was also well
00:41:03
beyond the range of the aircraft he was
00:41:06
flying seven hours passed again with no
00:41:10
accounting for the planes whereabouts
00:41:14
the 10:22 p.m. sullivan contacted a
00:41:17
miami tower once more this time he filed
00:41:20
a flight plan for Belize British
00:41:22
Honduras traveler 860 the official FAA
00:41:25
report states that he refueled just
00:41:27
after midnight in Cozumel Mexico this
00:41:30
was the last official sighting of the
00:41:32
plane
00:41:33
Jeffrey Sullivan his companions were
00:41:36
assumed lost at sea
00:41:37
[Music]
00:41:42
despite a massive search no trace of
00:41:45
Jeffrey Sullivan or Alex Rourke was ever
00:41:47
found
00:41:50
[Music]
00:41:51
23 years later Sherry Sullivan and her
00:41:54
attorney Karl McHugh petitioned the
00:41:56
United States government for information
00:41:58
concerning Sherry's father
00:42:00
to date they received over 5,000 pages
00:42:03
of documentation from 14 federal
00:42:05
agencies including the FBI and the CIA
00:42:11
very shortly after we initiated our
00:42:14
Freedom of Information Act request to
00:42:16
the FBI my attorney spoke with an FBI
00:42:20
agent on the phone
00:42:21
who wanted to question him about whether
00:42:26
he really wanted to get involved in this
00:42:28
type of thing it's suggesting that maybe
00:42:30
we'd be better off if we didn't he
00:42:33
indicated that we were opening a can of
00:42:35
worms as he put it more than a third of
00:42:40
the 800 pages received from the FBI were
00:42:43
censored
00:42:45
according to Sherry Sullivan information
00:42:48
found in these documents indicates that
00:42:50
at least another four hundred pages
00:42:52
exist but were withheld for national
00:42:55
security reasons it made me more curious
00:42:59
it was almost really the confirmation
00:43:02
where we're looking for it away saying
00:43:03
there is something here in the FBI
00:43:08
documents sherry found the named Floyd
00:43:10
Park
00:43:12
when she reached park by telephone he
00:43:14
told sherry had seen her father two days
00:43:17
after he reportedly disappeared floyd
00:43:23
park indicated that he had seen my
00:43:25
father and alex and spanish fella in
00:43:29
belly's we have not been able to verify
00:43:33
the identity of floyd park who he is
00:43:37
really and what he was involved in in
00:43:39
the 60s and how my father would have
00:43:42
known him you know why they would have
00:43:44
stopped to see him we weren't really
00:43:46
able to get those answers from him
00:43:49
sherry sullivan only talked to floyd
00:43:52
park once she's been unable to locate
00:43:55
him since but park did tell sherry that
00:43:58
her father and Alex Ward might have been
00:44:00
taken prisoner in Cuba I think it's a
00:44:04
very good chance if they ended up in
00:44:06
Cuba I mean they have involved in
00:44:09
clandestine operations in and out of
00:44:11
Cuba Fidel Castro from what I've heard
00:44:14
had a bounty out of my father and Alex
00:44:17
because he knew what they were involved
00:44:19
and he knew they were going in out of
00:44:20
his country so this a very good
00:44:24
possibility that they could have ended
00:44:26
up in Cuba probably some way they they
00:44:30
landed in Cuba in 1986 sherry spoke with
00:44:34
Marty Casey who had been in Cuba two
00:44:36
years after her father disappeared I was
00:44:41
with two Cuban exile from Miami and they
00:44:44
met the fellow that they knew from the
00:44:46
area he was working in the Cousteau most
00:44:49
us how many gonna see sorry medica okay
00:44:52
why no he recognized my American accent
00:44:54
I was speaking Spanish he asked me you
00:44:56
know working and I said what do you mean
00:44:59
O'Rourke O'Rourke na Roorkee the pilot
00:45:02
no LP not a Sullivan no no the other guy
00:45:05
was Sullivan is what should be the way
00:45:08
to pronounce it in Spanish and I said
00:45:11
well how do you know them and they said
00:45:12
I was in jail here with him two years
00:45:15
ago
00:45:15
yoky rockin birthday mucho de Dios or
00:45:18
cap no reason whatsoever to doubt it
00:45:20
because I was the one that thought that
00:45:25
work was over and I thought that work
00:45:28
was a pilot and he was the one who
00:45:30
corrected me he knew I didn't another
00:45:37
name Shari found in the FBI documents
00:45:39
was Enrique Molina Garcia allegedly a
00:45:42
double agent for Castro's government
00:45:45
Sherry believes Garcia was a mysterious
00:45:48
third man on the plane and that he
00:45:51
tricked her father and Alex work into
00:45:53
flying to Cuba unconfirmed reports do
00:45:56
place Garcia in Havana years after
00:45:59
chaeri's father disappeared
00:46:05
[Music]
00:46:14
when I was little I used to go over to
00:46:16
my grandmother's house and wind up his
00:46:18
watch all the time and that was my way
00:46:19
of keeping it alive I think he was in
00:46:25
that watch if I kept the watch going
00:46:27
he'd still be living and of course I'm
00:46:30
not little anymore but the little girl
00:46:33
inside me
00:46:34
the little seven year old girl that
00:46:36
never gave up hoping thinks he's alive
00:46:40
[Music]
00:47:07
for every mystery there is someone
00:47:09
somewhere who knows the truth perhaps
00:47:12
that someone is watching perhaps is you
00:47:16
[Music]
00:47:40
[Applause]
00:47:44
[Music]

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Episode Highlights

  • The Mysterious Disappearance of Debbie Wolf
    Debbie Wolf, a nurse, vanished after Christmas 1985, leading to a tragic investigation.
    “What you are about to see is not a news broadcast.”
    @ 00m 12s
    May 22, 2019
  • Uncovering Clues
    Debbie's family found oddities in her home, raising suspicions about her disappearance.
    “There were small things that were out of place that Debbie would not have put where they were.”
    @ 04m 37s
    May 22, 2019
  • Inconsistencies in the Investigation
    Debbie's family questioned the police's handling of the case and the evidence found.
    “I don’t think we did a dive of the pond or a complete search of the pond on that day.”
    @ 06m 59s
    May 22, 2019
  • The Discovery of Debbie's Body
    Debbie's body was found in a pond, but the circumstances raised more questions than answers.
    “Looks like a body down here.”
    @ 08m 21s
    May 22, 2019
  • A Mother's Belief
    Debbie's mother believes she was taken hostage and later killed, hoping for justice.
    “I think that she has a right to be put to rest finally.”
    @ 17m 05s
    May 22, 2019
  • The Psychic Encounter
    A psychic named Susanna reveals shocking details about Geneva's grandmother's past.
    “You want to ask me about your grandmother, don't you?”
    @ 26m 24s
    May 22, 2019
  • The Search for Truth
    Sherry Sullivan, Jeffrey's daughter, seeks answers about her father's disappearance.
    “I feel that there's somebody out there that knows what happened to her.”
    @ 32m 12s
    May 22, 2019
  • The Mysterious Disappearance
    Jeffrey Sullivan, a former Air Force pilot, vanishes during a covert mission in 1963.
    “That was the last time she ever saw him.”
    @ 33m 36s
    May 22, 2019

Episode Quotes

  • Debbie thought that helping people was the best thing in the world.
    Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode
  • There are people out there who know what happened to Debbie.
    Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode
  • Debbie was a lovely person and she was loved by very many people.
    Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode
  • I will always have that doubt of not knowing and I want to know.
    Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode
  • I think it's a very good chance if they ended up in Cuba.
    Unsolved Mysteries with Robert Stack - Season 3, Episode 14 - Full Episode

Key Moments

  • Unsolved Mysteries00:03
  • Family Concerns02:25
  • Flawed Investigation02:38
  • Body Found08:53
  • Murder Theories14:01
  • Search for Answers24:24
  • Endless Search32:12
  • Father's Last Mission33:36

Words per Minute Over Time

Vibes Breakdown

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