Freddie Roach once worked for infamous mobster Whitey Bulger: 'He was a really nice guy'

Kevin IoleCombat columnist
Freddie Roach opened up about his childhood job trimming Whitey Bulger's trees. (Getty Images)
Freddie Roach opened up about his childhood job trimming Whitey Bulger's trees. (Getty Images)

LOS ANGELES — David Letterman used to have a segment when his late night show was on NBC he called “Brush with Greatness,” in which audience members would recount the times they’d met a celebrity or some notable person.

Freddie Roach would have been able to fill an entire season with the many names from sports, movies, music, politics and other areas who have walked through the door at his Wild Card Gym.

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From Mark Wahlberg to Mickey Rourke, from Jesse Jackson to Shaquille O’Neal, Roach’s life has been full of celebrity encounters.

It all began, though, when he was a teenager living in Dedham, Massachusetts, and working as a landscaper for his father, Paul, who was an arborist. During dinner at a Hollywood restaurant to discuss Manny Pacquiao’s July 20 title fight with unbeaten Keith Thurman at the MGM Grand in Las Vegas, Roach told of the time that trimming the trees of one of his father’s customers led him to be interviewed by the FBI when he was just 14 years old.

The notorious mobster Whitey Bulger lived in Milton, Massachusetts, and hired a company to do his landscaping. As an arborist, Paul Roach was hired to maintain the trees on the property. The elder Roach tasked his 14-year-old son, Freddie, with trimming the mobster’s trees.

Bulger was the head of the notorious Winter Hill Gang that terrorized Boston for years. In 2013, he was convicted on 32 counts, including of participating in or ordering 11 murders. In 1974, Bulger was a feared figure in Boston while Freddie Roach was an amateur boxer of some note from a working class family who needed to help in the family business to earn extra money.

“He was a really nice guy,” Roach, who has trained Pacquiao on and off since 2001, said matter-of-factly. “He always treated us very well.”

But even when he was alone at Bulger’s home, Roach was never really alone. That’s because authorities kept a close watch on activity at Bulger’s home.

James "Whitey" Bulger, who was arrested in Santa Monica, California on June 22, 2011 along with his longtime girlfriend Catherine Greig, is seen in a combination of booking mug photos released to Reuters on August 1, 2011.
James "Whitey" Bulger, who was arrested in Santa Monica, California on June 22, 2011 along with his longtime girlfriend Catherine Greig, is seen in a combination of booking mug photos released to Reuters on August 1, 2011.

The FBI took the matter seriously, and in their desire to learn about Bulger, the teenage Roach was swept up in it.

“I did get questioned once why I was there by the FBI at a young age,” Roach said. “I said, ‘He hired me to work.’ They said, ‘Does he pay you for it?’ I said, ‘Of course he pays me for it.’ That came and went and never heard anything since.”

Roach was unaware of Bulger’s reputation. Bulger was a primary sponsor of the boxing team Roach was competing on and one of Bulger’s brothers sponsored the team for trips to the national tournament.

One of the members of Roach’s team was a local young man who was slightly older than Roach, Kevin Weeks. Roach recalled Weeks as being one of the better fighters on the team.

Despite being four years younger, Roach ribbed Weeks for being part of his high school diving team.

“I said, ‘Tough guys aren’t supposed to be on the diving team,’” Roach said.

Roach still occasionally hears from Weeks, who himself became part of Bulger’s gang.

After being released from prison in 2005, Weeks went on to write a book titled, “Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob.” Weeks had led authorities to the bodies of six men Bulger was suspected of having had murdered.

Bulger went on the run in 1994, but was captured in Santa Monica, California, in 2011, not far from Roach’s gym. But while Roach has had occasional chats with Weeks, he said he never again heard from or saw Bulger after he’d worked on his landscaping in the 1970s.

Roach is busy these days getting Pacquiao up to speed for the bout with Thurman. He said Pacquiao, who arrived in the U.S. for camp not quite two weeks ago, still hasn’t looked as sharp as he expects he eventually will.

“He’s been sparring every other day and we did 10 rounds of mitts the other day,” Roach said. “He looked really good on the mitts and so forth, but the sparring, he’s a little off a little right now because the jet lag is killing him. He hasn’t really slept soundly yet. He’s still having trouble with the jet lag a little, but by Tuesday, he should be fine.”

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