Owing money to a friend sucks. Owing money to a bookie really sucks. Owing money to the IRS beyond sucks. Owing money to notorious killer and Boston gangster Whitey Bulger? There are some choice words you can already think of regarding how badly that would suck.

There aren’t many people alive today who can probably say that they had the misfortune of dealing with the infamous gang leader, but UFC president Dana White is one of those people who can say they crossed paths in all the wrong ways.

Dana White interview
Dana White on Bussin’ with the Boys YouTube

How Dana White Met Whitey … Kinda

According to Sportskeeda, before Dana White became the renowned president of the UFC, he faced a harrowing experience with organized crime in his hometown of Boston. While running a charitable boxing program with Peter Welch, White became a target of James ‘Whitey’ Bulger’s Winter Hill Gang.

In the mid-1990s, two of Bulger’s enforcers demanded $2,500 from him, a sum that was daunting to White at the time. Fearful for his safety after repeated demands for payment, White hastily left Boston for Las Vegas, leaving behind his boxing venture.

In a twist of fate, White’s move to Las Vegas led to a chance reunion with his old school friend, Lorenzo Fertitta, at a wedding. This reconnection eventually resulted in the Fertitta brothers purchasing the UFC in 2001 for $2 million and appointing White as the president, marking the beginning of his journey in transforming the UFC into a global sports phenomenon.

Meanwhile, Bulger’s criminal empire came to an end with his arrest in 2011, years after White had successfully moved on to spearhead the UFC.

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Nina (Late) to the Rescue

When Nina Marie Daniele isn’t shooting guns in the desert with Sean Strickland or having Tom Aspinall ask if she’s ever been fingered by an MMA fighter, she’s usually continuing her usual antics of delivering some of the most informative and entertaining interviews in the fight business.

In a recent interview with UFC head honcho Dana White, she did that once again by giving White the most important gift of all – his freedom.

“I was like ‘what do you give the man who has everything?'” Daniele remarked after already giving White several framed photos of their faces photoshopped over cherubs.

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“Freedom,” she continued, pulling out a check for $2,500 signed to White. “I wrote you a check for $2,500 to pay back Whitey Bulger so you can go back to Boston and live your life as a free man.”

“Whitey Bulger is dead,” White said while laughing from shock.

Yes, he is Dana, yes he is.