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Part two of a two-part series. Read part one here.

He tore families apart, murdered their loved ones, and will now spend the rest of his life in prison, but could  James "Whitey" Bulger's underground crime world have extended even further than his convictions? In part one of this series, WGBH News senior investigative reporter Phillip Martin brought us the story of Owen Flynn, a West End bartender whose death in 1972 is getting renewed attention. In part two, Martin reports on new letters Bulger has written from behind bars and possible connections to the disappearance of Owen Flynn.
At one point during the trial of mobster James "Whitey" Bulger this summer, he turned toward the spectators' gallery and seemed to stare at Ann Flynn Dickinson, which prompted reporters afterward to ask her why.
"Maybe he thought he knew me or you know, I just couldn’t figure it out," Flynn Dickinson said.
But Flynn Dickinson saw in Bulger’s inexplicable stare an opportunity to try to communicate with one of America’s most notorious gangsters; to ask him if he knew anything about the mysterious 1972 disappearance of her father, Owen Flynn, at a time when Bulger was deep into a gangland war.
"I sat down and composed a letter and sent it to the prison and said, 'I am the person that sat in the front row the day that you stared me down not once but twice,'" she said. "I’m looking for information about my father’s disappearance ... ' and just went on in a one-page, very basic, kind of business-like form."

To her surprise, she ended up getting a response from Bulger a few days later.

Flynn Dickinson shared Bulger's letter with WGBH News. At the time Bulger wrote to Dickinson, he was at the Plymouth House of Corrections awaiting sentencing. In neat, cursive writing, Bulger began his response to Flynn Dickinson by stating:

Dear Ann, 

I read your letter over and over again a few times. It’s a very sad story … And I wish I had an answer for you. I don’t have any knowledge of the loss of your father. Please believe me. Because I want to help you, naturally, if I know anything I would never give any names but I’d tell you everything if it would help you.

But a former homicide detective who worked on past Bulger cases said that the disappearance of Owen Flynn matched Bulger’s methods: the wallet on the front seat, the keys on the dashboard, all of the vehicles left in Boston.
Owen Flynn was presumed drowned after jumping, accidentally falling, or being pushed into the Neponset River from the Granite Avenue Bridge that straddles Boston and Milton in December of 1972. His body washed up on Carson Beach in South Boston in January 1973, which raised questions for William Fleming, an MBTA lieutenant commander who has been looking into the case independently.

"Was this a suicide or was this a murder? I don’t know. I find the suicide part particularly hard to fathom. It just doesn’t make any sense," Fleming said. "If it was a suicide, why would someone jump into a freezing bay off the Granite Avenue Bridge, which is about a ten-foot drop and how could his body possibly wash up in Carson Beach?"
Fleming asked someone who might be able to answer both of these questions: Quincy Police Lt. Bob Gillan. As a police diver, Gillan said he has recovered far too many bodies at sea. He also dismissed the idea that Owen Flynn took his own life.
"It doesn’t pass the sniff test that someone would do that so close to the water," Gillan said.
If Owen Flynn was murdered -- by whom and why? In his response letter to Own Flynn's daughter from the Plymouth House of Corrections, Bulger suggested other possibilities:

"He goes on to explain his opinion about what might’ve happened without giving any names. And he gives three different opinions," Flynn Dickinson said. "One of them is that maybe the partners that my father was in business with had life insurance on him ... leave it to a criminal mind, obviously, and they’ll come up with some alternatives for you to think about."
Flynn worked as a bartender at Downey and Judge in the West End. 1972 was a boom time for bars in the neighborhood. Owen Flynn had just borrowed approximately $10,000 to come on board as a "silent partner."
The bar moved from Canal Street to 141 Portland Street. West End historian and archivist James Campano knew the place well, and said borrowing money from loan sharks for a piece of the bar was a common but sometimes dangerous decision.

Flynn Dickinson said it's not clear how her father came up with the money, or how he planned to pay it back. In his letter to Flynn Dickinson, Bulger also suggested that whatever happened to her father could have been the result of mistaken identification.

"He goes on to say maybe there was a mix-up," she said.
Specifically, Bulger’s letter states:

When I was young living in South Boston projects there was an Owen Flynn who was much older than I. Had a few sons, Owen was a big name back then, and he was  an ex-boxer. We spent a lot of time at the gym. He was an ex-World Champion.

But Paul Taylor, a former police officer and investigator with the Massachusetts Office of Licensure, met both Flynns and said it would have been hard to confuse them. At the time that he met Owen Flynn, Taylor said he was working as a bartender at Aces High in Southie, which was owned by Jack Brennan. The bar had a reputation as a police hangout. Taylor recalled seeing Owen Flynn from time to time at Aces High, and he also remembers the day when Flynn’s body washed up on Carson Beach.

"I remember saying to friends that I met that guy -- I know him. And, you know, the fact that he was friends with Jack Brennan -- I just figured he was coming to Jack for help for something because the only people that'd come in, they weren't part of the crew. The crew only came in when they wanted to get away from the crew," Taylor said.
Law enforcement officials I spoke with said there were several unsolved crimes during that period linked directly or indirectly to Bulger, and Massachusetts State Police Detective Lt. Steve Johnson, who worked on the Bulger Task Force, said that a reputation for murder worked to Bulger’s advantage.

"Even murders he wasn't involved in -- he wouldn't dissuade people from thinking he was because it would add to his aura and the fear factor that he would be able to place into people," Johnson said.  
But Bulger did not take credit for the death of Owen Flynn in his letter to Flynn’ s daughter.
"I did not kill your father," he wrote to her in closing.
But if Owen Flynn’s death in 1972 was the result of homicide, and if Bulger didn’t do it, who did, and why?  

Knowing, said Ann Flynn Dickinson, would be the greatest Christmas gift she and her family could ever have.