I don’t know. These both sound like the kind of stories that would be made up after the fact by somebody trying to salvage their reputation.
There’s no reason why Bulger would pay the lottery winner. The guy was in no position to negotiate. His only choices were hand over the money or be killed. He wasn’t even a regular business associate that Bulger had to keep sweet for future deals.
But stealing the winnings from a working class guy who won the lottery would be the kind of crime that would outrage the community Bulger lived in. It wouldn’t be Bulger stealing from some far-off rich guy; he’d be stealing from one of them.
So Bulger would want to put out the story that he had paid the guy for his share and it was all a scam to keep the feds off his back.
Same thing with being a snitch. Bulger had no motive to lie to the FBI. The mafia would kill him for working with the FBI regardless of the value of the information he gave. And the FBI was only going to protect Bulger to the extent he was giving them value for their protection. Once he got in bed with them, Bulger needed the FBI a lot more than the FBI needed Bulger.
And as above, it hurt Bulger’s reputation when it was revealed he was an informant. Nobody likes a snitch. Beyond that, it changed Bulger from somebody who had succeeded because he was tougher than everyone else into somebody who succeeded because he was working for somebody powerful who was protecting him. It changed Bulger’s image from being an attack dog to being the FBI’s pet poodle.
So again Bulger would want to salvage his reputation by claiming that he hadn’t really been working for the FBI. He’d rather claim that he had been successfully scamming the FBI.
I’ll admit I don’t know any details about Whitey Bulger. But I’ve known literally thousands of criminals and my experience is that they’re always telling lies about themselves in order to build up their reputation.
It probably helped immensely that so many FBI agents were Irish, as Bulger was. The feds LIKED Bulger , in a way they sure never liked Italian mobsters, and they cut him a huge, unforgivable amount of slack.
I always wondered, wasn’t ANYONE embarrassed that this creep’s brother was the most powerful legislator in Massachusetts? I have a hard time picturing “Tony Capone” as top dog in the Illinois legislature or “Paulie Gambino” as majority leader in the NY State Senate.
Plus, by the time the wheels were in motion, it was probably public knowledge to everyone - the lottery commission, the neighbourhood - who had won. If you had the winning ticket in a close-knit neighbourhood, everyone would hear about it within the hour. Killing the guy would not transfer the money, it would be counterproductive, since a dead guy could not attest that he had passed on his winnings to Whitey so the transfer probably would not be accepted as legit. however, a live guy, with a little persuasion admitting half his winnings belonged to his “close friend”, sounds legitimate enough to get away with.
According to the book Black Mas, John Connolly didn’t really bring Bulger in to the mafia case until Connolly’s boss was talking about deactivating Whitey because he didn’t seem to be vey valuable. Then Connolly inserted Whitey’s name into existing memos to make it appear Bulger was providing good intel. Flemmi did provide the FBI good info, but not so much Whitey.
Connolly, on the other hand, got a lot out of the Bulger relationship. He was the classic office bulshitter who made each little success sound like he split the atom. His entire career was built on having Whitey as a source and he was constantly bsing about his value.