What was Whitey Bugler's biggest mistake ?

I say getting involved in drugs and staying in the game too long .

He was a real piece of shit, but as far as getting away with his crimes he literally did every single thing right besides stay in one place for too long after he went on the run, and even that probably would have been ok of he didnt bring Greig with him. I mean its honestly amazing he had his top 3 closest guys all cut deals and tell on him, two of which did thier whole time and were released long before he even was caught.

His mistake was to go on the lam with the Craig. In black mass its write that was first identificated and this led to Bulger arrest.

I don't know if he made a "mistake" per se... he operated successfully for a while managing FBI and his own criminal doings (e.g., Greg Scarpa)... I think time just ultimately caught up with him as it does to everyone, and you can only walk a razor's edge for so long before you slip up sometime...

I think he did pretty well for someone who went on the lam

I bet he regrets ever getting in bed with john Connelly. He was a gangster and would have made money probaly would have went to jail way back in the 70tys with horse race fixing but he wouldnt have to live with being labeld a rat in his town of southie and the rest of boston. He thought he was a wiseguy diamond pinkey rings he spent alot of time it seems around made guys like nick femia and the anguilos. Theres even pics of him with vinny the animal. He asked jr russo to intervene when the winter hill guys in the early 70tys were gonna kill him. There was a funny story steve flemmi flipped out on him in florida when whitey showed him 2 kilos of coke well steve was driving them in a car like what the fuck you have that in my car for. I remeber a few years back my friend pulled out some ugly as nine i was just giving him a ride down the street i freaked out im said put that shit away and got him to the place quick n bolted. They dont play with guns in mass. I have a felony from a million years ago and what ever is in your car is yours. Not cool.

The underworld says Bulger was being a rat for the FBI, but imo it would be more correct to say that it was the other way around: the FBI (Morris, Connolly, Rico etc) were "moles" for him in the law enforcement. In a documentary about his trial, it's said he didn't even really help with relevant information against rival gangsters, Flemmi provided more than him, so for the feds it's less embarrassing to say he was a rat, an informant for them and to reluctantly admit they gave him too much freedom, rather than acknowledging he wasn't that useful, because in that case they would have to admit they allowed him to stay free just in exchange of bribes or "old friendship" in Connolly's case, that would make them look even worse because, had Bulger really been a valuable informant, then his FBI handlers would be guilty of negligence and abuse etc, but if he wasn't, then they are corrupt "moles" at his service and accomplices to all murders he committed in even a more direct way.

Mistake, what mistake, he was caught at what 83 after 16 year on the run. He hadn't done time or been arrested since the mid 1960's, I'd say he had a great run with few mistakes

Dwalin is right. In black mass is said that the fbi after Hoover for year said that the mob didn't exist tried everything to destroy the LCN families,plus bulger was a connolly idol when he was a child in southie so when connolly asked bulger to be an informant they speaked the same language aka was both irish,growned in southie and hate the italians. In the book is explained as connolly and his supervisor Morris was the real moles and helped to made fail more state police cases against the winter hill. In the 1970s and 1980s say that an fbi agent was corrupt was a blasfemy but was true.
Flemmi and bulger even gave 1000 or 2000 € for pay the airplain ticket to the Morris mistress or reach him because was in another state.
Bulger informations was nothing because as flemmi who was close to the Angiulos.

furio i dont mean to be rude but did u read my post above yours? Lol maybe english is not your first language but yoi litterally said exactly what I just said already.

No. I don't read your post i just read the post title and write my answer. Its not against you Mikey simply I dont read the post.

Haha ok im sorry furio! Maybe im a bit cranky today pr something sorry. Be well my friend

Basically that's what happened. Flemmi was the original snitch as I don't think Whitey was ever on Prince St., yet the Feds had details about the place that not just 'anyone' would know. Connolly just put Flemmi's files and others into Whitey's file so he could keep Whitey protected. I do think Whitey was a rat too, but the mafia stuff came directly from Flemmi I'm betting.

Whitey was a rat because connolly said that he know guys,of course bulger visit Angiulo at prince street because jerry know that is possible made money with him but he was useless to indicted angiulo.