Howie Carr (15 page)

Stevie’s flow of usable information, as opposed to gossip, was little more than a trickle, but the FBI’s protection never flagged. Zip Connolly’s next save came in early 1976. An excon and businessman named Francis Green owed $175,000 to a finance company with ties to Winter Hill. Accompanied by Johnny Martorano, Stevie and Whitey drove to the Back Side restaurant in Dedham to put the squeeze on Green. The deal was, they would receive a cut of whatever money they could wring out of him.

As they walked into the restaurant, Martorano spotted one of his old grade-school classmates—Bill Delahunt, the new district attorney of Norfolk County. As Whitey and Stevie found a table, Martorano walked over to say hello to the prosecutor. After a few pleasantries, they traded verbal jabs, and finally Delahunt told Johnny to stay in Boston and out of Norfolk County.

By then Green had joined the Bulger party, and Martorano walked over and sat down with them. From across the restaurant, Delahunt was now staring at the gangsters, but that didn’t deter Whitey.

“If I don’t get my money,” he said to Green, “I will kill you. I will cut your ears off. I will stuff them in your mouth, and then I will gouge your eyes out.”

Green went first to the Norfolk County district attorney, but the office punted to the FBI. And there the case died. It was becoming a pattern. Dennis Condon wrote the report, describing Green in the first sentence as “a convicted swindler.” He pointedly mentioned that Whitey was trying to collect for a woman, “a friend of theirs.” He wrote nothing about the threats.

Condon, however, would soon retire, taking a job in the administration of Governor Michael Dukakis. Another of Condon’s contemporaries, Bob Sheehan, would take his federal pension and become the state comptroller. The old guard was changing at the Boston office of the FBI. H. Paul Rico had retired from the bureau’s Miami office in 1975 after twenty-four years on the job. He soon had a new job—director of security for World Jai Alai, a gaming company based in Florida. Rico would soon be back in the middle of everything in Boston, but for now, he was relaxing in the Florida sunshine.

Meanwhile, Connolly was putting together a new FBI crew. Other than Zip, the most important agent for the future would be John Morris, who’d helped out on the Jimmy Martorano case. Morris and Dennis Condon both lived in Lexington and would commute into the city together. Soon Morris was one of the boys, and eventually Zip decided it was time to introduce him to Whitey.

In federal court, Morris later recalled Connolly’s instructions as to how he should handle Whitey: “Be sure to treat him with respect.”

When Morris finally met Whitey, he was surprised to see that Stevie Flemmi had also shown up. According to FBI regulations, informants weren’t supposed to be interviewed together; they weren’t even supposed to know who else was giving information to the bureau. But no one on either side seemed terribly concerned about the bureau’s rules.

“I wasn’t sure if they knew they were informants,” Morris said, in all seriousness.

Whitey still had provided no information of any consequence to Zip. He’d turned over the license plate numbers of a few troublesome Southie hotheads he wanted taken off the board, and he’d also passed on some negative, self-serving gossip about several political figures, including District Attorney Delahunt and at least one of Mayor Kevin White’s political operatives in Southie. Zip dutifully wrote up the “tips,” although he couldn’t have been satisfied with the quality of the information.

But as Whitey discovered, there were other ways to keep an FBI agent happy. In June 1976, the same month Jimmy Martorano was convicted, Whitey presented his first gift to Zip Connolly. It was a stolen diamond ring. Zip gave it to his first wife, as she would testify during his racketeering trial in 2002.

Meanwhile, the flow of “gold” out of the FBI office to South Boston continued unabated. Whitey next learned that a bookie named Richie Castucci had become an informant for the FBI. Castucci ran the Ebb Tide, the old Mafia hangout on Revere Beach where the Teddy Deegan hit had been planned back in 1965. Castucci was tight with Winter Hill—he’d introduced Flemmi and Johnny Martorano to a major New York book-maker when they were organizing Fat Tony’s race-fixing scheme. But then Castucci started feeding information to the FBI, and he passed on some information about two fugitive Winter Hill gangsters—Joe McDonald and Jimmy Sims. He knew they were hiding out in New York’s Greenwich Village, and he told the feds.

The penalty for such treachery was death. The Hill decided Richie Castucci had to go, but before they killed him, they planned to make a lot of money off him.

All through the fall of 1976, everyone in the gang bet football games heavily with Castucci. Even Whitey and Stevie, the nongamblers, took the plunge, because they had no intention of ever paying off Castucci, except with a bullet. For about half the season, the Hill remained ahead, and Castucci dutifully paid them off each Monday. But as the season wore on, the boys went into the red. They kept doubling up on their bets, but they couldn’t get even, and by Christmas, they knew it was time for Castucci to go.

He was told he could pick up his money in Somerville at the garage. When he got there, as Johnny Martorano later confessed, he handed Castucci a bagful of cash and told him to go to an apartment with two guys and count it. The two guys were Whitey and Stevie. Castucci was sitting in the apartment kitchen sorting the bills, with his back to the front door, when Johnny Martorano walked in and shot him in the head. Whitey and Stevie cleaned up the blood and wrapped the body in a blanket. Then they put Castucci’s body in the trunk of his car and drove it back to Revere, where they abandoned the vehicle in the parking lot of an apartment building.

To protect Whitey and Stevie, Connolly immediately began filing reports suggesting that Castucci was deeply in debt to both the Hill and the Mafia, and that Castucci settled with Winter Hill first. That was a fatal breach of organized crime protocol, Connolly wrote, because the Mafia always insisted on being paid off first. But the murder of an FBI informant required more than the usual duplicity. The day after Castucci’s body was found, the feds convened a multi-agency meeting to figure out who had murdered their informant. Representing the FBI was Zip Connolly. He suggested that the hit bore all the hallmarks of a Mafia assassination.

“Winter Hill doesn’t kill like that,” he said.

The legend of Whitey Bulger continued to grow, at least in the FBI reports filed by Zip Connolly. Soon Zip was claiming that Whitey had saved the life of an undercover FBI agent named Nick Gianturco.

Gianturco had been working undercover out of a warehouse in Hyde Park as “Nick Giarro.” The sting, which was called “Operation Lobster,” involved Gianturco setting himself up in operation as a fence, buying stolen goods from truck hijackers, mainly from Charlestown.

At one point, an associate of Stevie Flemmi’s asked if “Giarro” had any protection, because the associate was planning to rob him and didn’t want any repercussions.

Stevie phoned Whitey, who called Zip, who immediately got in touch with Gianturco and asked him if he had any meetings planned. Gianturco told him that he did, that night, but he’d already decided to blow the crew off because, wisely enough, he didn’t trust them.

As the years went by, Connolly and Morris increasingly exaggerated the importance of the tip. Morris eventually cited it as one of the two occasions on which Whitey’s information had prevented the murder of an FBI agent. During his testimony in 1998, Morris was asked to name the second agent.

“I cannot recall,” he said.

Whitey and Stevie had tried vending machines, and now Howie Winter and his associate Sal Sperlinga decided to put pinball machines into all the bars and veterans clubs in Somerville. First they got the Somerville aldermen to repeal the city ordinances outlawing the machines. But once pinball was legal, other, more legitimate businessmen quickly moved in, undercutting the Hill’s high gangster prices. In no uncertain terms, Howie Winter informed his would-be competitors that it was the Hill that had brought pinball back to Somerville, and that it was the Hill that would now enjoy the fruits of its monopoly. But instead of knuckling under, some of the other companies went straight to the Middlesex County district attorney, and soon the lantern-jawed first assistant district attorney, John Forbes Kerry, was announcing the arrests of Winter and Sperlinga.

The pinball arrests in late 1977 were a major break for Whitey and Stevie. Howie was the undisputed boss, and Sperlinga one of his top money men. With both of them off the street, Johnny Martorano was the last remaining at-large Winter Hill hoodlum who outranked them, so to speak.

The pinball machines, though, were just the beginning of Howie Winter’s troubles. One of Fat Tony Ciulla’s crooked jockeys had been arrested in New Jersey, and he flipped. Once the Garden State jockey implicated Ciulla, Fat Tony cut a deal for himself with prosecutors, and then he sold his story to
Sports Illustrated
, which put it on the cover of its November 6, 1978, issue. In the piece, Ciulla didn’t mention the names of anyone from Boston, but in New Jersey, a judge ordered Fat Tony to reveal the names of the gangsters who were involved in fixing races with him in Massachusetts.

“Your Honor,” he complained, “I don’t know if I am allowed to say these names here in open court.”

The judge didn’t care about federal grand juries. “You are here now,” he said.

Fat Tony took a deep breath and began speaking.

“Fellows that were partners of mine,” he began. “One’s name is Howie Winter. One name is John Martorano. M-A-R-T-OR-A-N-O. Whitey Bulger. Stephen Flemmi.”

It was the first time Whitey’s name had been mentioned in a federal courtroom since 1956.

By January 1979, Whitey was in deep trouble. During Fat Tony’s run, he and Stevie had been in charge of finding bookies willing to take action on the fixed races. Like everyone else, they’d made a lot of money over the years, but now Fat Tony had put them squarely in the middle of the conspiracy, along with everyone else in the gang. With Howie Winter and Sal Sperlinga already in state prison on the pinball machine case, it looked like the end of the line for Winter Hill.

But then Zip Connolly went to bat for Whitey. He had to—he was already on Whitey’s payroll, often leaving his government paychecks uncashed in his desk at the JFK Building in Government Center for months at a time. Zip’s new side-kick, John Morris, would also soon be accepting Whitey’s cash. Now the two feds would really have to earn their keep, by deep-sixing a much higher-profile case than that of shakedown victim Francis X. Green or the botched takeover of the vending machine racket. The FBI agents went to Jeremiah O’Sullivan, the head of the federal organized crime strike force. They made a simple pitch: The FBI was preparing to bug Gerry Angiulo’s Mafia headquarters, the Dog House, at

98 Prince Street, and they needed both Bulger and Flemmi as sources. It was an easy sell, and the race-fixing indictment was quickly rewritten to include both Whitey and Stevie only as unindicted co-conspirators.

Everyone else in the gang was indicted for fixing horse races, and those who weren’t convicted, fled. Using information from their new friends in law enforcement, Whitey and Stevie got word to Johnny Martorano ahead of the indictments, and he vanished. But before leaving, Johnny turned over some valuable names to Stevie Flemmi, one of them a state trooper who had funneled inside information about various investigations to Martorano over the years.

Martorano also passed on the names of his contacts at the telephone company, who had provided numbers for, among other things, the Eddie Connors telephone booth hit in 1975. Martorano still had his loansharking money out on the street, but during the seventeen years he was on the lam in Florida, Whitey and Stevie would send him about a million dollars in cash. In return, Martorano would come in handy as a hitman in the years to come.

Once they dodged the race-fixing indictment, it was back to work, shoveling underworld shit to the FBI in return for federal gold. Now that Richie Castucci had been murdered for being a rat, the FBI needed someone else to help them keep tabs on fugitive gangster Joe McDonald. This was a perfect chore for Whitey, and he took up where Castucci had left off when he was murdered for providing the sort of information that Whitey would now willingly pass on to the feds.

Three times in the summer of 1979 Connolly filed reports on what Whitey told him about McDonald’s activities, whereabouts, and drinking habits. Based on Whitey’s information, the FBI made no arrests, and no one was hit for tipping off the feds. The Boston office of the FBI wasn’t really interested in arrests, only in deluding its superiors in Washington that it was keeping tabs on organized crime. And Whitey wasn’t truly concerned about rats, only about making money off them. He just wanted to rip them off, the way he had Castucci, before murdering them on the grounds that they were informants.

On October 16, 1979, Jimmy the Bear Flemmi died of an apparent drug overdose at the state prison in Norfolk. In 1975, while serving an eleven-to-eighteen-year sentence for assault with intent to commit murder, he’d received one of the state’s first weekend furloughs from prison. Like an early Willie Horton, Jimmy had immediately fled, and was not apprehended until three years later, in Maryland. He was forty-seven when he died.

Meanwhile, Stevie’s mother had been mugged again in Mattapan, by a mob of fifty blacks, and a photo of her sitting outside her car, on the pavement, dazed and bloody, had appeared on the regional Associated Press wire. Stevie was fed up.

He needed to relocate his parents to a “nice” neighborhood—an all-white neighborhood. He asked Whitey if he knew of anything available in Southie, and Whitey told him that the house at 832 East Third Street, next door to his brother Billy’s at 828, happened to be for sale.

It would be a good place for the Flemmis, Whitey told Stevie. And it would be a convenient place for everyone to meet— Whitey, Stevie, their FBI agents, and even, on occasion, Billy. The house included an enclosed sun porch, which, if weather-proofed, would be usable year-round. The sun porch would be perfect for storing things—machine guns, silencers, even the bodies of young women.