Howie Carr (11 page)

The new, consolidated Winter Hill Gang soon began flexing its muscles. They wanted to control gambling north of the city, and that meant eliminating another crew of independent mob-sters led by Indian Joe Notarangeli, who operated out of Mother’s, a barroom under the elevated tracks of the Green Line at North Station.

The Notarangelis controlled a number of bookies in the Merrimack Valley, and they were stubborn. In March 1973, a bartender from Mother’s was killed by machine gun fire at a stoplight in Brighton. He had no connections to organized crime. His fatal error: He drove a Mercedes-Benz that looked a lot like one owned by Indian Joe’s brother Al.

Eleven days later, Whitey was in the front seat of an automobile with an Uzi machine gun as a Notarangeli hood named Al Plummer drove down Commercial Street in the North End. Whitey opened fire, practically decapitating Plummer and wounding another gangster in the car, an old associate of Stevie Flemmi’s named Hugh “Sonny” Shields.

The third person in the car was a hoodlum named Frank Capizzi, who had been wounded twice earlier by Winter Hill hit squads, namely Whitey. After the third shooting, on Commercial Street, he and his family fled Boston, crisscrossing North America to escape. As he wrote to a judge in 2003, his children “had the job of cleaning festering wounds and picking out bits of lead from my back as they surfaced.”

Four days later, on a Friday night, they caught up with Billy O’Brien, a thirty-two-year-old roofer and stevedore from South Boston (no relation to the Billy O’Brien who was murdered in 1967). O’Brien, who had served time for killing yet another hoodlum named O’Brien, in South Boston in 1964, was driving on Morrissey Boulevard. He had bought a cake at Linda Mae’s before picking up his ten-year-old daughter, Marie, for the weekend. In the car with O’Brien was another rackets guy named Ralph DeMasi. As they headed north, another car pulled up alongside them and the passenger opened fire, again with a machine gun. O’Brien was hit seventeen times, and died instantly. DeMasi was wounded.

“I thought someone was taking target practice on the road,” DeMasi said in a letter to a judge in 2004. “It was my good friend John Martorano.”

The driver: Whitey Bulger.

Eleven days later, a different pair of Winter Hill killers flew down to Fort Lauderdale to murder an ex-boxer from the Notarangelis’ hometown of Medford. When he opened the door to his apartment, the associate of Indian Joe was shot five times in the head.

By April 18, Indian Joe had abandoned Mother’s. He retreated to his home turf, Medford Square, a bustling downtown area with heavy pedestrian traffic and narrow, clogged streets. About 3:45, he walked into the Pewter Pot coffee shop, used the pay phone, and then sat down and ordered a coffee.

He hadn’t been there long when Johnny Martorano walked in, wearing construction clothes. Johnny shot Indian Joe twice, then walked out of the restaurant and jumped into a car driven by an older man with “stubby fingers,” as one witness put it.

Ten months later, in February 1974, Johnny Martorano caught up with Indian Al, shot him in the head, and left his body in the trunk of a stolen car in Charlestown. Days later a couple of Charlestown teenagers took the car for a joy ride. The cops caught up with them in Somerville. In the trunk was the frozen corpse of Indian Al.

The Hill began calling in, one by one, the bookies who’d been laying off their action to the Notarangelis. One of the calls went out to Jackie McDermott, the top bookie in Lowell. McDermott was summoned, as he later told the story, to the Holiday Inn on the Somerville-Charlestown line and escorted to Room 13. Whitey was there, but Howie Winter did most of the talking, and McDermott did all of the agreeing. What choice did he have?

Finally, when all of the arrangements had been made, McDermott was told he was free to leave. He nodded, but said he had just one question he’d like to ask.

“Why’d you hit Joe like that, in front of so many people? Right downtown there, in broad daylight?”

Whitey Bulger threw in his two cents’ worth: “Because we wanted to show everyone how easy it is.”

Whitey was in the gang, but he still wasn’t of it. The other gangsters appreciated his impeccable Boston police and courthouse sources; even the Mafia would come to rely on Whitey to keep them informed. Gerry Angiulo would say to him, “Whitey, you can find out a little more than me...”

But he was still the odd man out in Boston organized crime, the one guy from Southie, the city’s overwhelmingly Irish neighborhood. Somerville was at least as Italian as Irish; Howie Winter was married to an Italian woman. The Martoranos and Frank Salemme were half-Irish. Whitey, though, was what the others laughingly called FBI—full-blood Irish. It didn’t disqualify him from membership in the gang, but it did set him apart from everyone else.

Now, though, the FBI was about to construct for Whitey his own little mini-crew, a gang within the gang. The two men who would become his closest associates—FBI agent John “Zip” Connolly and mobster Stevie Flemmi (from an Irish neighborhood, married to an Irish woman)—were about to return to Boston.

Flemmi had been on the lam since the fall of 1969. By early 1972, he was holed up in New York, but he wanted to return to Boston, and the FBI wanted him back. Flemmi was, after all, the best kind of organized crime informant—an Italian hood who was trusted by the Mafia, but who had no compunctions about informing on them. The problem was, he still faced a pair of outstanding warrants, for the Billy Bennett murder in 1967 and for the car-bombing of Barboza’s lawyer, a semi-shady underworld attorney named John Fitzgerald. The Bennett murder was disposed of quickly, when two of the other defendants were acquitted of the charges by a Suffolk County jury.

The Fitzgerald bombing, though, was more complicated. It had occurred in Middlesex County, where it was more difficult to broom a case than in Boston. And the lawyer was, at least in the public mind, a civilian who had merely happened to be in the wrong place at the wrong time. Fitzgerald had lost a leg in the bombing, which made him an even more sympathetic figure. In short, Middlesex County needed a scalp, and Condon had one picked out—Stevie’s old partner, Frank Salemme, who was also hiding out in Manhattan.

If everything could be worked out properly, Salemme’s capture would be good for everybody—except for Salemme, that is. Rico and Condon wanted the credit for the pinch to go to their new protégé in the bureau, Zip Connolly.

Zip was yet another native of the Old Colony Harbor projects. He’d graduated from Boston College in the same class with Johnny Martorano’s brother, Jimmy, then briefly, unhappily attended law school. In 1968, Zip was at loose ends, and he needed some advice. He ran into Paul Rico’s partner, Dennis Condon, and Boston police detective Eddie Walsh, an old friend of the Connolly family’s. Both Condon and Walsh would later brag that they had “recruited” Zip. Then Connolly stopped by the State House to visit his old neighbor and now state rep, Billy Bulger, to discuss career opportunities in law enforcement.

On August 1, 1968, U.S. House Speaker John McCormack wrote a personal note to his old friend J. Edgar Hoover on behalf of a constituent.

“Dear Edgar,” the letter began. “It has come to my attention that the son of a lifelong personal friend has applied to become a special agent of the Federal Bureau of Investigation....”

Zip was appointed to the FBI in October 1968. He began his FBI career in Baltimore and then San Francisco before he was transferred back east to New York. But like Stevie, he still wanted to get back to Boston, to be closer to his ailing father. Condon and Rico were bumping up against the FBI’s mandatory retirement age, but Connolly was just a kid, barely thirty. He could be their go-to guy in the Boston FBI office for the next twenty years, whatever their second careers turned out to be.

But first they had to get him back to Boston. Connolly was the guy who could take down Salemme. Every few days, Flemmi and Salemme would get together in Central Park. They’d sit on a park bench and swap secondhand gossip about what was going on back in Boston. One day, early in 1972, as soon as they sat down on a park bench, Stevie delivered some big news.

“I’m getting out of here,” he told Salemme. “It’s too hot down here.”

His next stop would be Montreal, Flemmi explained to a stunned Salemme. And as Flemmi prepared to flee, Condon began establishing the paper trail to explain Connolly’s impending capture of Salemme.

In 1998, under oath in federal court, Condon was asked about all the memos he sent to Connolly in the days before Salemme’s arrest.

“I believe I sent him a couple of photographs [of Salemme] and said: See if you can spot—spark them up down there.”

Once Stevie was safely out of New York, the plan to make Zip Connolly a hero could proceed. In 2003, Salemme told congressional investigators what happened almost immediately after Stevie fled.

“Shortly after that,” Salemme said, “I was bumped into by John Connolly on 83rd Street and 3rd Avenue.”

By the time Salemme was shipped back to Massachusetts to stand trial for the bombing, Stevie Flemmi was safely established in Montreal. He would say later that those were the best years of his life. On the witness stand, he later claimed, unconvincingly, that he didn’t even want to return to Boston. He said H. Paul Rico made him come back. Working at a print shop, Stevie kept up with the Salemme trial in the Boston papers. The case went badly for Frank—he was convicted of bombing the car that belonged to John Fitzgerald and shipped off to state prison for sixteen years.

But the main witness against Salemme also testified that Stevie was not present at the bombing. Then he vanished, not to be seen again for twenty years. In May 1974 Rico called Stevie in Montreal and told him it was time to come home.

Once the charges against him were officially dismissed, Stevie was warmly welcomed back at the garage on Marshall Street. Stevie moved back in with his mistress, Marion Hussey, in Milton, and was soon sleeping with her fifteen-year-old daughter as well. He found another girlfriend, Debra Davis, at a Brookline gas station, and when her father objected, he drowned mysteriously. In short, it was business as usual for Stevie, and business as usual meant talking to the FBI.

But now there would be someone else in the mix—Whitey. Unlike Stevie, Whitey still hadn’t been officially “opened” by the FBI as an informant. Later Zip invented a story about how he recruited Whitey as an informant as they sat in an FBI car on a moonlit night at Carson Beach in 1975.

But the reality was less cinematic, and more pragmatic. It was an arranged marriage between Whitey and Stevie, and the marriage broker was the Federal Bureau of Investigation. Once Zip was back in Boston, Billy told him to keep Whitey out of trouble. That would be Johnny Martorano’s testimony, and Billy, under oath, didn’t deny it.

As Flemmi testified in 1998: “[Whitey] didn’t just approach me cold and say: ‘Hey, here’s what I’m doing,’” Flemmi said in 1998. “I mean, it didn’t make sense. I would have been wondering what was going on here.”

In court, Flemmi said that Whitey approached him one day in the garage in 1974 and told him he was talking to Connolly. Later, Whitey would tell Stevie that Connolly wanted to meet him, and that the introduction would be handled by Dennis Condon. They met in what Flemmi described as an “obscure” coffee shop in Newton. It was a cordial get-together. Flemmi asked how Paul Rico was, and Condon said he was fine. It was, Flemmi said, “like a transition.”

By 1975, Whitey had officially joined Flemmi as a Top Echelon informant for the FBI. It was quite a feather in his cap, considering that he had spent almost his entire post-prison career in the South Boston rackets, and had practically no access to the information that the FBI was still most interested in gathering—about the Mafia. Stevie was much more tied into Prince Street and the Angiulos’ satellite crews in East Boston and Revere. Stevie would talk to the Mafia, and pass on whatever he’d learned to Whitey.

And Whitey would pass it on to Zip, who would write it up, giving most, if not all, of the credit, to Whitey. The question that has always lingered is, why exactly did the FBI need Whitey if they had Stevie?

The answer was, they didn’t need Whitey nearly as much as they needed his brother Billy. The retirement age for agents was fifty, and they always fretted about their post-FBI jobs. Their federal pensions weren’t nearly as large as they would later become. It was easier for a retired agent to find a new job if he knew somebody, and if he hadn’t made any enemies. And what was so wrong with helping out the brother of a rising legislator who might someday be in a position to put in a good word for a retiring, middle-aged agent?

Whitey was an informant, after all. He did meet, first with Condon, then Zip, and finally other agents as the years went by. And, according to FBI regulations, some informant had to be cited for every bit of information in each report—so why not Whitey? Stevie came up with enough information for two people, and if Whitey got credit for some of the tips, well, how exactly was that a problem? No money was changing hands, at least not yet. And if, down the road, some retired agent from the Boston office were to become Boston police commissioner or director of security for Boston Edison—well, so be it. It wouldn’t be the first time either of those jobs had been given to a politically connected retired G-man.

As time went by, and Billy solidified his grip on state government, Zip would make a habit of inviting the new agents to a tour of the State House, where he would introduce them to the Senate president, “the most powerful man in the state,” as one of the corrupted agents later described Billy.

Things were looking up for Whitey, but he still needed to eliminate some of his old rivals in the Town. Spike O’Toole, an old friend of the McLaughlin brothers, was the first to go. He was a regular at the Bulldog Tavern on Savin Hill Avenue, even though the bar’s owner, an ex-prizefighter named Eddie Connors, was tight with Howie Winter. Connors tipped off Howie about Spike’s pub crawls, and Winter told Connors to give him a call the next time Spike was tying one on at the Bulldog.