Hitman

by Howie Carr

  Back then, on his left wrist he’d worn a Presidential Rolex watch, featuring emerald-cut diamonds around the face, inlaid with authentic mahogany that matched the dashboard of his black Mercedes 560 SEL, which he parked next to his thirty-three-foot Holiday Rambler RV.

  Everything was of course long gone now—sold off to pay his legal fees.

  * * *

  THE UNSEEN presence in the Miami courtroom, day after day, was Whitey Bulger. He was the Winter Hill hoodlum who had captured the imagination of the general public, at least until the cops started digging up the bodies he’d buried around Boston over the years.

  Unlike Martorano and the rest of the Hill, Whitey and Stevie had enjoyed police protection for more than twenty years. FBI agent Connolly, now sitting at the defense table, was their go-to guy in law enforcement. Growing up in South Boston, Zip had always worshipped Whitey’s younger brother, Billy Bulger, who with the assistance of the FBI had become the president of the state senate, the most powerful politician in Massachusetts.

  After fortuitously timed federal investigations had eliminated Billy Bulger’s rivals in the legislature, Billy Bulger had asked Zip for one last favor. “Mr. President,” as Billy preferred to be called, wanted Zip to keep Whitey “out of trouble”—or so Whitey had told Martorano. At the time it had seemed a reasonable enough story. But now Casabielle was asking Martorano why he never got suspicious as everyone in the Winter Hill Gang kept getting arrested, except for two guys.

  Whitey and Stevie.

  * * *

  IN FEBRUARY 1979, the entire hierarchy of Winter Hill was indicted for running a multistate conspiracy to fix hundreds of horse races. Everybody was charged except Whitey and Stevie. On cross-examination, Martorano told Zip’s lawyer that he was “happy” when Whitey told him that he’d managed to avoid the federal indictment.

  “Did you not wonder why [Whitey and Stevie weren’t arrested]?”

  “They told me why. Whitey said because John Connolly was able to keep him out of it.”

  “Did you wonder why John Connolly would do such a thing for Mr. Bulger?”

  “Because one of his promises was to help Billy Bulger maintain his position by keeping his brother out of the trouble.”

  “Today, do you still believe the same thing?”

  “I sort of believe it still, but I think there was more to it than that.”

  “But you are not so clear, are you?”

  Martorano thought for a moment about his old friend Whitey. “There was a lot of truths that he said to me, not just all lies.”

  “You didn’t really know who Mr. Bulger was, did you?”

  “Well, I felt I knew him. We were partners. I mean, we had a lot of crimes we committed together. I felt he was a stand-up guy.”

  * * *

  IN MIAMI, Johnny Martorano was back in familiar territory, where he’d spent sixteen years. After he fled Boston in 1979, just before he was indicted in the race-fixing case, he lived mostly in South Florida until his arrest in January 1995. Then he’d been shipped back to Massachusetts. At the Plymouth County House of Correction, he’d lived for more than two years with his codefendants—all except Whitey, of course, who had already vanished.

  The rest of them had been charged in a racketeering indictment—nothing about any of the dozens of murders they’d committed collectively, and individually. But Johnny Martorano had only been arrested on the old race-fixing charges. He was looking at four to five years, tops. So he just sat tight in the jail as the lawyers wrangled over the usual arcane pretrial legal issues in court. Every day he spent in the Plymouth County House of Correction before the trial would count as part of his eventual sentence.

  But in 1997, Stevie and Whitey were disclosed as informants. As part of pretrial discovery, the FBI began turning over its informant files to the defendants. Johnny Martorano suddenly learned that for all those years he and Whitey and Stevie had been committing crimes together, they’d been informing on him, and on the rest of the gang, to the FBI. Whitey and Stevie—his sons’ godfathers—even had their own personal informant numbers, just like the numbers the cops had on their badges. That fact alone bothered Martorano enough to mention it, unsolicited, during the cross.

  “I never believed they were informants,” Martorano told Casabielle, “when we were out shooting people.”

  “Obviously they were with you when you were out shooting people?”

  “Obviously.”

  “So they know you had shot people. Can you tell how many people they were present for that you had shot?”

  “I don’t know.”

  As far back as the 1960s, Johnny Martorano learned from the yellowing FBI reports, his friend Stevie Flemmi was calling him a pimp behind his back, and trying to frame him for murders Stevie himself was planning to commit. It was all right there in the FBI reports—the 209s and 302s, many of them written by agents who were being paid off by the gang, including Martorano himself. But neither Whitey nor Stevie had ever mentioned any of the murders to their G-man handlers. So Stevie still had one card left to play against Johnny: he could rat him out for all the murders they’d committed together. After living large all these decades, with his immunity from prosecution, now Stevie Flemmi could betray Johnny one final time.

  But this time Johnny Martorano understood what was happening, and he was determined to stop the rat. He had to act quickly, though, before Flemmi could move against him.

  “I was concerned,” Martorano was telling Zip’s lawyer. “Now I know they could possibly implicate me, my brother, all my friends.”

  “You did it for your friends?”

  “I did it for a lot of them, yeah.”

  “So you did the right thing?”

  “I still believe I did. I mean, I didn’t think anybody else got hurt by Flemmi or Bulger after the fact.”

  “You did the right thing, Mr. Martorano?”

  “Yes.”

  “Did you always do the right thing?”

  “I tried. But I don’t think I always did the right thing.”

  * * *

  JOHNNY’S NEGOTIATIONS with the feds took more than a year, part of which he spent in the hole at the federal prison in Otisville, New York, but in the end Johnny Martorano was finally offered a sweet deal by the feds. As Casabielle told him, “They wanted you really bad.” Because Johnny Martorano had the goods on Stevie and Whitey and Zip Connolly, and because he knew just how solid his information was, he held out.

  For forty years, even when he was a fugitive, Martorano had moved easily among all the crews and factions in the Boston underworld, Irish and Italian, black and white, Mafia and independents. He was the one fish the feds couldn’t afford to let slip through the net. And so eventually they cut him exactly the plea bargain he had held out for: he would testify, but only against Whitey, Stevie, and Zip. For appearance’s sake, the Justice Department lawyers added the names of a few more minor wiseguys, mainly from Whitey’s South Boston crew. But they were just filler: How could Martorano testify against hoodlums he’d never even met, let alone committed crimes with? Under the terms his lawyers painstakingly hammered out, Johnny would not have to testify against his brother Jimmy or against his fellow Winter Hill gang leader, Howie Winter. And Johnny Martorano would end up doing twelve years, for twenty murders.

  “Did you ever calculate how many months you did per body?” Casabielle asked Martorano.

  “No.”

  “Could it have been about seven months?”

  “Could have been.”

  “That’s a pretty good deal, isn’t it?”

  “I had good lawyers. I made a good deal. I don’t deny I made a good deal.”

  * * *

  THE JUDGE was giving defense lawyer Casabielle a free hand. The prosecutors had gone through the list of killings in a perfunctory manner. But Zip’s lawyer, knowing he had the jury’s undivided attention, was still trying to pile as many additional gory details onto the record as possible. He wanted the jurors to be
disgusted that their government would cut a deal with a killing machine like Johnny Martorano.

  Flemmi, Casabielle knew, would not be nearly as effective a witness when he took the stand after Martorano. With his twitches, and his stuttering when challenged, the seventy-four-year-old Flemmi was easier to rattle. And he had trouble keeping his stories straight from one deposition or trial to another.

  As Casabielle went over the list of Martorano’s twenty victims, Johnny often admitted to killing hoodlums because he thought they might testify against someone he knew, or because they had disrespected one or another of his friends. But Casabielle preferred concentrating on the law-abiding citizens—the civilians—that Johnny Martorano had murdered by mistake. Like Michael Milano, a bartender Martorano machine-gunned at a stoplight in Brighton in 1973. Milano died because his new Mercedes and a long fur coat made him look like his employer—a gangster whose North Station bar the Hill had staked out.

  “You killed him by mistake?” Casabielle asked.

  “Not by my mistake,” Martorano said. “Somebody said that was a certain guy we were looking for.”

  “Did you know what that person looked like?”

  “No,” said Martorano.

  “So you went out looking for someone you didn’t know, that you didn’t know what he looked like, and by mistake you shot Mr. Michael Milano?”

  “Somebody else said that was him.”

  “And you took that person’s word?” Casabielle said.

  “Yes.”

  “That was enough for you to kill somebody?”

  “At the time, yeah.”

  * * *

  A COUPLE of murders later, Casabielle brought up a guy named William O’Brien. The Hill had been looking for a tough ex-con named Ralph DeMasi, and O’Brien was driving him on Morrissey Boulevard in Dorchester. They had just left a meeting at which they’d been trying to buy guns for the gang war in which the bartender had been killed a couple of weeks earlier. They were headed for South Boston to pick up O’Brien’s ten-year-old daughter Marie. It was her birthday, and he had a cake for her in the backseat of the car. But O’Brien never made it back to South Boston. A Winter Hill hit car pulled up alongside his and Johnny Martorano opened fire with a machine gun, killing O’Brien and wounding DeMasi.

  Casabielle asked Martorano about William O’Brien.

  “I didn’t know him. I was looking for the other guy that was with him.”

  “So William O’Brien, again, was a mistake?”

  “It could have been.”

  “We are talking about somebody that was possibly innocent.”

  “He was possibly guilty, too. They both showed up looking to buy guns to kill someone.”

  The O’Brien hit was one of at least five murders committed by the Winter Hill Gang in 1973–74, when they were settling a score for the Mafia with a rogue organized-crime crew. Martorano explained how the other gang, which the Hill completely destroyed, had started the war by killing an LCN bookie—“his name was Paulie,” Martorano said, “I forget his last name.”

  After the gang was wiped out, Johnny Martorano and Howie Winter went to the North End, and Jerry Angiulo, the Mafia underboss of Boston, gave them $25,000. But Johnny Martorano steadfastly maintained he never took money for killing people, not even from the Mafia and Jerry Angiulo.

  “That was like a donation from him,” Martorano said of the $25,000, “for our help.”

  Then Casabielle mentioned a 1981 murder he did in Oklahoma for John Callahan, whom Johnny would murder in Florida a year later. Callahan gave Martorano $50,000 after he traveled to Oklahoma to murder the owner of Callahan’s former company, who had to die because he suspected Callahan had been skimming money from his jai-alai frontons.

  When he got the money, Johnny gave half of it—$25,000—to his driver on the hit, fellow Winter Hill fugitive Joe McDonald. Then he split the remaining $25,000 with Stevie and Whitey back in Boston. So Johnny Martorano had banked a little over $8,000 for his nineteenth murder.

  “Was that also a donation?” Casabielle asked.

  “Positively.”

  “What charity were they donating to?”

  “To Winter Hill.”

  “Are you seriously telling this group of people that the money … was a contribution to Winter Hill, the Winter Hill charity? Is that your testimony?”

  “It was a gift from him [Callahan]. He was so happy he didn’t get indicted. Better than giving it to a lawyer, I guess.”

  At that point Casabielle didn’t even bother to point out that a year after accepting the $50,000, Martorano killed the guy who had given it to him. Later Johnny would tell the jury he “felt lousy” about having to “kill a guy who I had just killed a guy for.”

  “It was very distasteful,” he elaborated.

  Instead, Casabielle stayed with the larger theme of the Winter Hill gang as a charity, returning to the money the Hill accepted for wiping out a small rival gang for the Mafia.

  “And what good deeds did Winter Hill do other than kill people and feel good about it?”

  “I believe they helped a lot of people over time.”

  “And they hurt a lot of people as well?”

  “Yes.”

  “Are you saying to this group of people that when Mr. Angiulo gave you $25,000 for those murders, that was also a contribution to the Winter Hill charity?”

  “Correct. He was giving us money because we killed a guy who killed his friends.”

  “And your testimony, sir, is that you don’t kill for money?”

  “No.”

  As the lawyer continued this line of questioning, Johnny Martorano was thinking to himself, Does this guy really believe I’d kill somebody for $8,000? For a million maybe, but eight grand? Nobody risks his life for eight grand—a junkie possibly, but nobody else. Jerry Angiulo understood that—it was just a nice gesture he’d made, splitting up the fifty large like that. He was cutting up a score with his partners, which is what the Winter Hill Gang was with the Mafia—partners.

  * * *

  IN THE end, though, everything always seemed to come back to Whitey. After all the books and movies and FBI press conferences, after all the “age-enhanced” mug shots and all the dozen-plus segments about him on America’s Most Wanted, most people still didn’t get it. In the Boston underworld, until rather late in his career, Whitey had always been a small-timer, a ham-and-egger. He was from Southie, where a gang war was cowboys biting off one another’s noses outside barrooms in the Lower End, driving around and shooting point-blank at each other—and missing.

  Now that he had disappeared, though, Whitey had become a legend, a criminal mastermind, when all he really was was a rat. Zip Connolly’s lawyer was trying to draw that bitterness out of Martorano, asking him what he thought now of his youngest son’s godfather.

  Casabielle: “He was dishonest with you for how many years, twenty-five, thirty years?”

  Martorano: “From ’72.”

  When Johnny first got to know Whitey Bulger, Whitey was already forty-three, a late bloomer in criminal terms. Whitey had been shipped off to prison for bank robbery at the age of twenty-six in 1956, when Johnny was fifteen. Whitey didn’t return to Boston until 1965. Johnny was running bars in Roxbury while Whitey was on the Rock—Alcatraz.

  The first time Johnny actually sat down with Whitey, in early 1972, Whitey was up to his eyeballs in one of those slapstick Southie gang wars. He was being hunted all over town by younger, quicker hoods. Which was why he’d shown up at Johnny’s bar in the South End, dressed in a suit. Whitey needed a favor—he asked Johnny to introduce him to Howie Winter over in Somerville.

  He wanted Howie to use his muscle to settle the war over in Southie, even if it meant that Whitey’s boss would have to be killed, not by Whitey of course, but by some of the guys in the other gang, the ones who had been chasing Whitey. No wonder Johnny’s pal Joe McDonald had never trusted Whitey as far as he could throw him.

  So Johnny and Whitey didn’t g
o way back, the way Martorano did with Stevie Flemmi. Stevie he’d known since he was practically a kid. He’d killed guys for Stevie—well, he’d killed at least one guy in Southie for Whitey, too, but by then it wasn’t personal, it was business, a Winter Hill rubout. But after all the favors, when Johnny Martorano went on the lam in 1979, Whitey told him that from now on he should do all his talking on the phone to Stevie. Whitey didn’t do phones. Phones could be tapped.

  Now Casabielle was again asking about Johnny Martorano’s relationship with the two rats in his gang.

  “Mr. Flemmi and Mr. Bulger were dishonest with you, correct?”

  “Technically,” Martorano replied.

  “What do you mean, ‘technically’?”

  “With that [being informants]. But they were honest about a lot of things. You can’t be dishonest without showing some honesty.”

  “That’s part of the charade, isn’t it?” Casabielle said.

  “Yeah,” Martorano said, with a slight sigh, “I guess.”

  * * *

  BY 1988, Johnny Martorano had been on the lam for almost a decade. During that time, he’d killed two more guys for Whitey and Stevie. But his monthly cut from the Winter Hill rackets back in Boston continued to dwindle, and what could Johnny Martorano do about it from Florida? Whitey was the big shot now, and Martorano the supplicant. And Whitey was tiring of his responsibilities to his one-time partner, the guy who had once saved his life.

  In 1987, Whitey had been recorded on a DEA bug saying, “Fuck Howie” and “There is no Winter Hill Gang.” But even as they were writing off their old Somerville partners, Whitey and Stevie were rolling in drug money. They were making more money than the old gang from Winter Hill had ever dreamed of—$5 million “protection money” from one marijuana dealer alone, Stevie would later brag.

  And yet … the cops left Whitey and Stevie alone. If any police ever did make a move against them, they were slapped down, transferred, demoted, or forced to retire. The FBI, the Massachusetts State Police, the Boston PD—nobody could ever seem to build a case against “the two guys,” as they had become known on the street. After a while, few cops even tried.