It wasn’t long before Shea answered the siren call of the streets. And it wasn’t much longer before Whitey Bulger caught wind of this kid — a fearless brawler with brass balls who was nonetheless a stand-up guy. After a few tests of loyalty, Bulger figured he’d found a new soldier. He entrusted the kid with running his lucrative drug trade.
“It was an honor,” says Shea. “It was a privilege. I was in awe. He was the legend. He was the king. Who wouldn’t want to be like Whitey? A kid growing up in that environment, seeing the respect that he got, seeing the power that he had. Nobody fucked with Whitey.”
The common folktale in South Boston was, of course, that Bulger was keeping drugs out of the neighborhood. In fact, the opposite was true. In those days, the ’80s, cocaine was huge in Southie (as it was seemingly everywhere). And Whitey Bulger was getting his cut. “It really was run like a corporation,” says Shea. “But one thing he never let in was heroin and angel dust. He kept those two out. Strongly.”
Whitey Bulger was a drug kingpin. Extortionist. Racketeer. Murderer. And, to Red Shea, he was a father. He instilled important life lessons. “ ‘Don’t drink too much. Watch how you drive. Don’t drive fancy cars. Keep yourself clean-cut. Don’t lose your temper like that.’ I appreciated all that,” says Shea. “He was always saying, ‘Read a book, John. Read a book. Make sure you read a book, John. Reading’s really good for ya.’ Those things stay with a guy who’s never had a father.”
Even as he was living the high life — pulling down $15,000 to $20,000 a week, taking trips to Miami and Montreal, wearing Armani suits, uncorking $300 bottles of wine — Red Shea was still a 21-year-old kid. He looked up to Whitey and Steven Flemmi and Kevin Weeks. “Every one of them guys I learned something from,” he says.
That’s what hurts him the most. He gave his life to these people. Gave up the woman he loved and, under other circumstances, would have married. (“I loved being a gangster more than anything, and that’s the reason I never got married. Being in that life, you should never bring a family into that life.”) He spent a dozen years in prison rather than break the code he lived by. But Whitey, Steve Flemmi, Kevin Weeks, all the Southie guys who preached the Irish mob’s omerta — few of them followed their own example. “When it came time,” Shea says with a rueful smirk, “the majority of them were the great pretenders.”
He was in prison when he learned the truth. The rumors had been circulating for years, but he’d have none of it. He wouldn’t allow himself to believe them. Then one day, a friend called from home and played him the TV news over the phone. Whitey Bulger was a top-echelon FBI informant and had been for years. He was King Rat. “I felt like someone had reached down the wire, right through me, grabbed my heart, and tore it out,” he writes. Shea says now, “It was one of the hardest pills I’ve ever taken in my life. I could have given him up in a heartbeat and done no time. I could have. But I didn’t. I defended him. To the very end.”
