How one man survived life as a Boston gangster



Sean Scott Hicks doesn’t care what you do with his new memoir, “The Devil To Pay: A Mobster’s Road to Perdition” (Blackstone).  Like it, hate it, use it as kindling to thwart off the chill of winter, I don’t give a flying f–k what you do with the book at this point,” he writes. 

A Cedar Junction prison at the Walpole penitentiary — one of many correctional facilities where Hicks was held. Boston Globe via Getty Images

“Completing it was a burden I needed unloading, a shat I needed shat, returning the weight back to Atlas, all 12 steps of recovery wrapped up in a nice bow — take your pick, whatever metaphor suits you best.”

Hicks’ apathy is understandable. 

For half a century, the serial criminal walked a “well-trodden road to eternal damnation” that saw him spend over 20 years in more than a dozen different prisons. His rap sheet encompassed conspiracy, racketeering, counterfeiting, money laundering, bank robbery, kidnapping, aggravated assault and attempted murder. 

He started young.

Born in Weymouth, Mass., in September 1971 to a “s–t-faced” mother and a father he never met, he was first exposed to the country’s most powerful Irish American mob, the Winter Hill Gang, when his mother was dating mob fixer William “Red” Baker while simultaneously having an affair with Bill Winter, older brother of Howie T. Winter, the gang’s leader. (The gang’s most infamous member, of course, is long-time bandit Whitey Bulger, who evaded capture for decades.)

Lt. Deputy Samuel J. Boike, left, and Lt. Raymound Peck of the Somerville Police, right, escort Howard Winter into Middlesex County Court in 1979. Boston Globe via Getty Images

He liked what he saw. “It was about one thing: respect. The money, power, and responsibilities were just by-products, but pretty f–king good ones if you ask me,” he writes. 

When his formal education ended at age 10, Hicks found himself working for mobster Toby Rust, bagging 50 bucks a time to empty trucks of hijacked whiskey and cigarettes.

He also collected loan repayments and stole cars and, later, became involved in the more violent side of mob work. 

The result, explains Hicks, was that he skipped manhood. “I went from boy to monster,” he writes. But he was clever.

When he was 16, Hicks converted an old lobster boat so it had a hidden vault, perfect for transporting contraband. “The space was only just large enough to hide a couple hundred pounds of cargo or one large man,” he explains.

It was big business. Within three months, he expanded. “I took every penny of profit … and added three more boats to my burgeoning fleet of quasi pirate ships,” he writes. 

Later, he turned to garbage disposal for criminals, although he drew the line at the dead. But he did investigate how to dispose of bodies. One option was sodium hydroxide that “completely dissolves the flesh,” he writes.

The other was feeding it to pigs.  “However cliché, pigs do eat anything … but that doesn’t mean it can digest everything. For that reason, hair must be shaved and teeth must be pulled.”

While in prison, Hicks was a model inmate — but only so he could get out early. 

During his time in Massachusetts Correctional Institution in the 1990s, he attended courses in anger management, understanding addiction, engine maintenance and even hairdressing.

His good behavior saw his seven-and-a-half year term reduced to a third of his original sentence.

A flow-chart of the Winter Hill Gang’s power structure. Reuters

He wasn’t entirely clean. Each week, Hicks received packages containing heroin, coke and marijuana which he passed via associates who stored it by “putting it in the vault.”

He also had a regular supply of “eighty-proof spring water.”

“There was no f–king way I was going to stay sober for seven and a half years,” he writes. “It was cheap rotgut shit, but I didn’t give a f–k. 

“I was loaded by lunch, and the days went by quicker.”

But as Hicks writes, “being a model inmate did not translate to me being a model citizen.” Just four months after release, Hicks was indicted for a stolen traveler’s check scam and for his association with an incident that saw NBA star Paul Pierce stabbed in Boston in 2000.

Inside prison and out, Hicks reconciled his actions with alcohol. “The angel on my shoulder went on a 30-year bender, leaving the devil to call the shots,” he writes.

After another prison release in 2016, he drank himself into a three-day coma only to be discharged from hospital “and thrown back into my s—ty existence.”

It was only after his ninth and final release, in 2020, that Hicks finally found freedom. 

A weapons cache seized during a 1987 Boston gangland bust. Boston Globe via Getty Images

This time, none of his old partners in crime, armed with liquor and another job to do, were there to greet him. “There was nothing outside and I couldn’t have been happier,” he writes.

Today, Hicks is sober. He is also an actor, producer and a rapper, releasing tracks under stage-name “Ghost,” the nickname he acquired during a two-year spell on the run from the police. 

There are regrets, but not many. “Looking back on everything, it all seems so f–king crazy. 

“It’s no wonder I wound up the way I did. A disastrous childhood, a cataclysmic adolescence and an apocalyptic adulthood,” he reflects. “Not exactly a recipe for success, is it?”

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