Iconic Boston Irish mob boss James (Whitey) Bulger’s infamous Winter Hill Gang touched down in Detroit in the mid-1970s. It was almost his demise. Instead, because of Bulger’s highly-controversial relationship with the FBI in Massachusetts, the trip made by a lieutenant of his to the Motor City indirectly led to him gaining even further control of the rackets in his hometown of South Boston than he already had.

Whitey Bulger’s story is currently being told on the big screen in the critically-acclaimed film Black Mass, starring Johnny Depp as the demonic and calculating Bulger, serving life behind bars for murder and racketeering. He was a fugitive of the law for 16 years until his apprehension in California in 2011 where he had been living for most of the previous decade and a half. His Winter Hill Gang was a hodgepodge of mostly Irish and Italians hoodlums, thieves and professional killers operating out of “Southie” and suburb Sommerville, Massachusetts, from the 1970s into the 1990s.

Winter Hill Gang member Anthony (Tony the Fixer) Ciulla, the preeminent horse-race fixer in North America in the late 1960s and first half of the 1970s, was sent to Michigan in 1975 to engineer an extensive race-fixing ring to be staged at multiple tracks throughout Metro Detroit in a joint venture with the traditional Italian mafia, specifically the local Zerilli-Tocco crime family, New York’s Genovese crime family and Philadelphia’s Bruno crime family. Ciulla’s arrest less than two years later and subsequent decision to turn informant spawned hoards of convictions, 40 in all when it was all said and done.

It should have bagged Bulger, but his unholy alliance with federal authorities spared him, while not being so kind to his fellow Boston Irish crime lord Howie Winter, in a horse-race fixing related to the ponies running at Pocono Downs in rural Pennsylvania that landed in 1979. Winter’s conviction in the case and removal from the streets (he did 8 years in federal prison) paved the road for Bulger to take unchallenged command of the Winter Hill syndicate and complete gangland supremacy in Boston’s Irish underworld.

And it probably wouldn’t have happened if Ciulla – pronounced CHU-LA – had never stepped foot in Detroit. That’s where he finally got jammed up, finally took the arrest that led him to flipping. Michigan was his Waterloo and ultimately his downfall.

The whole operation was practically doomed from the start. First and foremost for the fact that the horse-racing industry in the Motor City was maybe the most mob-corrupted and federally scrutinized in the entire country back then. The feds in Detroit had been itching to connect the area race circuit and organized crime for years. So when the large, imposing and rotund Ciulla sauntered into town, carrying with him his colossal-sized reputation and set up shop at The Derby bar located a block away from the Zerilli-Tocco syndicate-owned Hazel Park Racetrack, the feds saw their chance and Tony the Fixer he became Public Enemy No. 1 for the Detroit FBI office.

Hazel Park Raceway, opened in 1949 and located two miles north of Detroit’s city limits, was a college graduation present from Michigan Italian mafia “founding fathers” Joseph (Joe Uno) Zerilli and Vito (Black Bill) Tocco to their sons and future local mob leaders, Anthony (Tony Z) Zerilli and Giacomo (Black Jack) Tocco. For years, rumors of illegal activity at the state-of-the-art racetrack ran rampant, but authorities never attained enough hard evidence to file charges.

After the younger Zerilli was busted for hidden ownership in and the skimming of six million bucks from The Frontier Hotel and Casino in Las Vegas and sent to prison in 1974, the Detroit mafia’s control of the racetrack was vulnerable. The state of Michigan was already pressuring Zerilli and Tocco to relinquish ownership. The Ciulla case would be the death blow.

Ciulla grew up in the Boston-area mob hotbed Revere, Massachusetts. Instead of joining the city’s traditional Italian crime syndicate, he gravitated towards the mainly Irish Winter Hill Gang, which was an offspring of the old Mullen Gang, the last group standing in the aftermath of the massive and carnage-strewn Irish Mob War of the 1960s and early 1970s. Before he reached his 30th birthday, the boastful and behemoth-sized (6-foot-4, 350 pounds) Ciulla was well known all up and down the east coast as the best pony fix-it man in the business.

After learning his trade in Boston, he traveled to other locales, to manipulate horse-race outcomes, places like New York, New Jersey, Maryland, Florida and Pennsylvania, as the Winter Hill Gang made alliances with Genovese Family acting boss Anthony (Fat Tony) Salerno and Philly mafia don, Angelo (The Docile Don) Bruno. Salerno’s Genovese clan was one of New York City’s “Five Families” and lorded over large portions of the rackets in New Jersey. Budding Philadelphia wiseguy Pasquale (Pat the Cat) Spirito was Bruno’s representative in the race-fix scams.

Soon, Ciulla was asking his superiors for permission to take his show on the road to the Midwest, gangland territory long run in tandem by the mafia families in Detroit and Chicago. With Metro Detroit being home to not one, but two successful and allegedly mob-regulated racetracks (Hazel Park Raceway in Hazel Park, Michigan and The Detroit Race Course in Livonia, Michigan), set his targets on Motown.

Sometime in the early spring of 1975, Salerno and Bruno reached out to the legendary and fast-aging Detroit Godfather Joe Zerilli and asked permission to send Ciulla and his crew there in return for a piece of the action. Zerilli, who sat on the American Mafia’s National Commission alongside Salerno and Bruno, agreed and by the first week of May, Tony the Fixer touched down in “The D” and went to work.

The Derby Bar was their headquarters and heavily surveilled by the FBI, tipped off almost immediately of the Ciulla crew’s presence in town by informants on the street. Hazel Park Raceway rested in walking distance from the tavern and Ciulla himself bounced between the two properties all day. With mob prince Tony Zerilli away in prison, his first cousin Jack Tocco, was in charge of the track on a day-to-day basis – for most of their co-ownership Zerilli was the man calling the shots at the track.

On the heels of Tony Z’s incarceration, Black Jack replaced him as heir apparent to the syndicate throne his father had reigned atop for 41 years. Upon Joe Zerilli’s death of natural causes in 1977, Tocco took over as boss, naming Tony Z his underboss, a union that lasted until the 2000s.

Tony the Fixer had a tightknit crew. Besides him there was Robert (Bobby the Teacher) Owen, Salvatore (Sally Mac) Macarano and Oscar (Fat Jerry) Friedman. They were all experts at infiltrating racetracks, getting access to the jockeys and stables on the grounds and muscling, maneuvering and greasing enough palms to loot the place. Bobby Owen was Ciulla’s right-hand man. He was tasked with overseeing affairs crosstown at the DRC. FBI agents would watch every evening as Owen arrived at The Derby Bar to rendezvous with Ciulla, Sally Mac and Fat Jerry and review the day’s receipts, proceeds, debts and payoffs.

Using a well-stocked cadre of informants tied to the area horseracing scene, the FBI began constructing a case. It was a slow burn, but by the summer of 1976 the heat was on and dominoes started to fall, laying groundwork for future arrests. On several occasions throughout the Bicentennial summer of 1976, the FBI ordered that sports books in Las Vegas pull all races running at Hazel Park Raceway off the board for days, even weeks at a time.

Faced with a pending federal racketeering indictment in Michigan, Tony Ciulla jumped ship in late 1976, latched on with Team U.S.A. and opened up the floodgates on his co-conspirators far and wide. He testified at numerous grand juries and trials across the country in the forthcoming years.

“He gave us everyone he was working directly with, we couldn’t believe how deep he was connected,” retired Detroit FBI Special Agent in Charge of Organized Crime Oscar Westerfield. “The more he talked, the more wide spread we realized his fixing reached. The government was able to male a multitude of cases based on his cooperation. He helped us bring down guys in a half-dozen states. That kind of informant doesn’t comes along very often. All the stories he had could fill a library.”

Tony the Fixer’s appearance before a grand jury in Detroit was the final nail in the coffin for the Motor City mafia’s strangle hold on the horseracing industry in Michigan, leading to the ouster of Jack Tocco and Tony Zerilli from ownership in Hazel Park Raceway by state authorities.

One snippet of grand jury testimony showed how much sway and intimidation Ciulla held at the Hazel Park track.

“I had the whole place wired….if the jockeys didn’t do what I said, they got hurt….this one jockey didn’t dump a race when I told him to so I smacked him six ways to Sunday, every way but loose, left him bleeding on the stable floor.”

While nobody in the Detroit mob wound up getting bit in the indictment, Ciulla’s whole crew and a lot of racetrack staff at Hazel Park Raceway and The DRC did. Hurt most by Ciulla’s cooperation was his own Winter Hill Gang. A 1979 indictment related to fixing races at Pocono Downs in Wilks-Barre, Pennsylvania sent more than two dozen Winter Hill Gang members and associates to the can. The No. 1 defendant in the case was Howie Winter, the only man in South Boston who’s power in the underworld matched that of the notorious Whitey Bulger. Winter’s imprisonment left Bulger the undisputed king of Southie and set the stage for his murderous, yet federally-protected decade-and-a-half reign in the east coast rackets.

Bulger’s absence in the Pocono Downs bust wasn’t for lack of information (he was actually cited as an unindicted co-conspirator) – Tony the Fixer filled the feds in extensively about Bulger and his role in that fix, as well as many others. However, Whitey was left out of the indictment. He was left out of a lot more of them in subsequent years before he was finally bagged in a 1995 bust because of his relationship with corrupt FBI agent John Connolly. The shocking alliance between Bulger and Connolly (born and raised around Whitey in his Southie stomping grounds) was eventually revealed via aggressive reporting by the Boston Globe newspaper. Connolly is currently serving time in prison for second-degree murder based on his connection to a gangland homicide carried out by Bulger and his Winter Hill henchmen.

Ciulla died of a heat attack in 2003 at 60 years old. He had entered the Witness Protection Program following his turning against the mob and lived, first in California and then back in Massachusetts before he passed away. Winter is a free man and recently penned a book.

The sale of the Hazel Park Raceway caused strife in the relationship between Detroit mafia moguls Jack Tocco and Tony Zerilli, with Zerilli claiming Tocco withheld proceeds that were rightfully his. That strife boiled over into full-fledged hatred at the end of their lives. Convicted together in a RICO case from the 1990s, when they walked out of prison in the 2000s,Tocco ordered Zerilli and his family shunned. Tocco died of natural causes in July 2014, Zerilli wasn’t far behind, succumbing to old age in March of this year.

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