Dana White vs the Boston Irish Mafia: Discuss

Whitey Bulger’s mugshot for his incarceration at Alcatraz in 1959. | Photo by Donaldson Collection/Michael Ochs Archives/Getty Images

Or: Was Whitey Bulger a better boss than Dana White? Early indicators say YES. The st…


Whitey Bulger’s mugshot for his incarceration at Alcatraz in 1959.
Whitey Bulger’s mugshot for his incarceration at Alcatraz in 1959. | Photo by Donaldson Collection/Michael Ochs Archives/Getty Images

Or: Was Whitey Bulger a better boss than Dana White? Early indicators say YES.

The story’s been told so often you suspect the reason it’s been told so often sits somewhere outside the parameters of why one would tell the story to begin with. But here goes…in the middle of teaching his fairly successful cardiokickboxing class, way back when, in Southie, some men walk up to Dana White, the now CEO of the UFC, and tell him they need to speak to him.

He says, what he feels is somewhat obvious, that he’s in the middle of a class. They just stand there and in the brief seconds between shock and awareness he realizes that he’s talking to Kevin Weeks, the duly appointed representative for Boston Irish mob head Jimmy “Whitey” Bulger.

They ask him for cash, if he wants to continue running a fairly successful cardiokickboxing class. He claims to have no cash. They give him a deadline to come up with the cash he claims to not have. Failure to come up with the cash is precisely the kind of arithmetic that got White’s ass on a plane out of Boston, and so begins the origin-lycra-tights-to-riches story he’s made sure we haven’t forgotten.

Nothing at all wrong with that. Nothing outside of me knowing Kevin Weeks.

On the occasion of doing a chapter for my book FIGHT, Or Everything You Ever Wanted to Know About Ass Kicking But Were Afraid You’d Get Your Ass Kicked for Asking, I flew to Boston. By arrangement Weeks was to meet me at the place I was staying and our day was to be structured around the need to talk and not much else. Weeks, a lifelong martial artist and boxer himself, it was felt, might have some valuable insights to offer. That and he had a book scheduled to be out soon too. His book was called Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob.

He pulled up in what I remember as a gray late model sedan of some sort. He came to the door and I hustled my way out to greet him noting that his appraisal of me was quick, but complete and felt laser focused. By the time we crossed the street to his car I knew he had done the character math particular to both cops and criminals. When your business is knowing the men you’re dealing with better than they know themselves, if you last long enough, you probably do it well.


Read the rest of the post on the Bloody Elbow Substack, where we detail the UFC’s earnings and debt, along with Endeavor’s own projections as they name two possible risks to their lucrative MMA business.

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