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  Once again, to Kathy, and to my mother

  Contents

  Title Page

  Dedication

  Acknowledgments

  Prologue: Miami 2008

  1. “Always Be a Man”

  2. Apprentice Gangster

  3. Gang War

  4. The Animal Flips

  5. Bwana Johnny

  6. The Winter Hill Gang

  7. Indian War

  8. Glory Days

  9. The Bubble Bursts

  10. The Fugitive

  11. The Last Hit

  12. “You Can’t Rat on a Rat”

  Where Are They Now—2010

  Index

  Copyright

  Acknowledgments

  First of all, thanks to my beautiful wife, Kathy, and our three daughters—Carolyn, Charlotte, and Tina—for their forbearance during the writing of this book. And Carolyn, thank you for your assistance in bailing me out of whatever computer difficulties I was grappling with from day to day.

  Obviously, this book could not have been written without the cooperation of Johnny Martorano. I sought him out on his return to Boston, and eventually he came around to the idea that his life story could serve as the framework for a larger tale, a history of organized crime in Boston over the past half century.

  We spent hours together, much of it in the city room of the Boston Herald early Sunday mornings. He talked, I listened. Everything that has been said about his memory is true. Not only does he have a near-photographic recall of details, but he’s also a first-class raconteur. As one of my Herald colleagues who got to know Johnny on those Sunday mornings put it, “If only he wasn’t so damned likable.” He also introduced me to a number of his friends and associates, who had their own stories to share and whose memories refreshed Johnny’s recollections, as a lawyer might say in court. I appreciate everyone who shared their stories with me, although I won’t name them, for obvious reasons.

  I hope that the photographs will add a different dimension to this book. I would like to thank everyone at the Herald, where I have worked for so many years, for their assistance. For allowing me to print many of the photographs, I owe a particular debt of gratitude to Pat Purcell, the owner and publisher of the Herald. Thanks also to the staff of the Herald’s library, which came up with clippings about ancient crimes. Photographer Mark Garfinkel also provided invaluable assistance.

  As for the mug shots, most of them were made available to me by people who probably wouldn’t appreciate being identified here. But I hope they know how much gratitude I have for their assistance. The two organizational charts of the Winter Hill Gang, from 1975 and 1982, were made available to me by the Drug Enforcement Administration (DEA) and the Massachusetts State Police (MSP). Many thanks, especially to DEA agent Dan Doherty.

  My great friend Larry Bruce spent what must have seemed to him like endless hours getting the mug shots into publishable form, and I appreciate it more than I can express. I would also like to thank my radio producer, Nancy Shack, for all her help on the book in so many ways.

  Much of this book is based on public records and police reports. To break up the text, I occasionally used transcripts of Johnny’s testimony at the two Zip Connolly trials, in Boston in 2002 and in Miami in 2008. He was asked many of the same questions at both trials, and I used what I considered the more compelling of his answers.

  I am grateful to all who provided me with the FBI reports quoted in the book, and also thanks to the Boston Police Department’s public-information unit, from which I obtained the official accounts of murders sometimes dating back more than forty years.

  Bob Gleason, my editor at Forge, has been a pleasure to work with. He and his staff, especially his assistant Ashley Cardiff and editor Eric Raab, did yeoman’s work molding the book’s various elements into a coherent whole. Along with Larry Bruce, Eric’s skillful handling of the photos gave this book its unique look. George Tobia, my agent as well as Johnny’s, put together the deal in his usual professional matter.

  Finally, for introducing me to Bob Gleason, I owe my friend Bill Martin, the bestselling novelist, more than one gift certificate to Fleming’s Steak House or the Hanover Street Chophouse, whichever he so desires.

  Prologue: Miami 2008

  JOHNNY MARTORANO WAS choosing his words carefully. It was September 17, 2008, and he was sitting in the witness stand in a state courtroom in Miami. The sixty-seven-year-old hitman was being cross-examined in the murder trial of a corrupt FBI agent from Boston, John Joseph Connolly, Jr.—better known as Zip, the nickname bestowed upon him by his underworld paymaster, the legendary gangster Whitey Bulger.

  Zip Connolly was already more than five years into a ten-year federal sentence for racketeering. And now in Florida he was facing life for the 1982 murder of a businessman who’d made the fatal mistake of throwing in with the Hill—the Winter Hill Gang of Boston—of which Johnny Martorano was a founding member.

  Martorano had actually pulled the trigger on the businessman, John Callahan, a good friend of his—the twentieth and final murder of his career. But state prosecutors were contending that the murder at the airport in Fort Lauderdale had actually been orchestrated by the “highly decorated FBI agent,” as Zip Connolly was invariably described in the newspapers.

  Zip was accused of convincing the Hill that Callahan could implicate all of them, gangsters and FBI agents alike, in an earlier string of murders involving the takeover of a jai-alai company.

  At Zip Connolly’s first trial for racketeering, in Boston, Martorano had been the prosecution’s chief witness, and Zip’s attorneys hadn’t been able to lay a glove on him. Now, in Miami, another high-powered defense lawyer was having a go at Martorano, and he, too, was flailing. The lawyer, Manuel Casabielle, had already told the judge during a sidebar conference that simply being in the presence of Martorano was intimidating him.

  “It feels scary when you are close to him,” Casabielle whispered. The Dade County jurors didn’t seem frightened, though. They appeared mesmerized by his tales of the Winter Hill Gang, a collection of unusually murderous mobsters.

  At its peak, the Hill’s cast of killers had included Martorano, admitted murderer of nineteen men and one woman, as well as Stevie “the Rifleman” Flemmi. The Rifleman was now doing life for ten murders, and in various other court appearances Flemmi had taken the Fifth Amendment when asked about nine other slayings he’d never been formally charged with.

  Finally there was James “Whitey” Bulger, a fugitive since 1994, number two on the FBI’s Ten Most Wanted List behind only Osama bin Laden. Just two weeks earlier, on his seventy-ninth birthday, the FBI had doubled the reward for his capture to $2 million. Whitey, who hadn’t been seen in the United States since 1996, was charged with twenty-one murders.

  What Johnny Martorano hadn’t known during his gangster days was that both Whitey Bulger and Stevie Flemmi were informants for the FBI—rats, as Johnny would put it. And for that he could never forgive them.

  Whitey and Stevie hadn’t been just Johnny Martorano’s partners, they were among his closest friends. Stevie was the godfather of Johnny’s middle son, christened in 1970 when Stevie was a fugitive from murder and car-bombing raps in Boston
. Whitey was the godfather of Johnny’s youngest son, Jimmy, born in 1986, when Johnny himself was on the lam, in Florida, living less than thirty miles from the courthouse where he was now testifying.

  But Johnny Martorano was an even more fearsome killer than his two Winter Hill cohorts. In a few days, Stevie Flemmi would testify that after Martorano had become a fugitive in 1979, he had always kept the FBI informed of Johnny’s whereabouts. But the FBI never moved to arrest him, Stevie explained, because Johnny was a life insurance policy of sorts for the feds’ star underworld informants Bulger and Flemmi. The Mafia in Boston would never dare move against the two “independent” gangsters as long as Johnny was still out there … somewhere, capable of avenging his two sons’ godfathers, the two guys he thought were his best friends.

  “Johnny Martorano was a boogey-man to the Mafia,” Stevie Flemmi would testify. In fact, Stevie’s older brother, another notorious Boston hitman known as Jimmy the Bear, had once taken—and botched—a Mafia contract on Johnny’s life. The Bear was another of Martorano’s closest friends—he’d been the godfather of Johnny’s oldest son. But like so many of Johnny’s old pals, the Bear was gone now, dead of a drug overdose in state prison.

  * * *

  IN THEIR direct examination, the state prosecutors had already gone over the complete list of Martorano’s twenty murders, hit by hit. Between 1965 and 1982, he’d killed fifteen whites and five blacks, in three states. Their bodies had been dumped in alleys, in ditches, or left in the trunks of stolen cars. One corpse had never been found. Johnny Martorano killed them in telephone booths, at airports, at stop signs, on the open highway, and in coffee shops, as they left barrooms drunk or snorted cocaine in a parked car.

  The jury now knew that he had mostly used a .38-caliber snub nose revolver, although he’d killed three others with a carbine, two more with a grease gun, and one with a sawed-off shotgun. One time he was the driver when Whitey and Stevie took out a guy in a phone booth. And then there was the pimp that Martorano had stabbed to death while out on a date with a nurse.

  It was standard procedure in these kinds of cases for the prosecution to put onto the record everything that seemed even vaguely unseemly, before the defense could do so and make it appear to the jury that the government was hiding something.

  So all Connolly’s defense lawyer could do was re-ask as many of the same questions about Martorano’s blood-soaked past as the judge would permit, and hope for an opening. Casabielle was reading aloud from Martorano’s plea agreement with the state of Florida to testify in any and all prosecutions. The lawyer asked him if that was why he had come to Miami.

  “I’m keeping my word to the government and I’m being honest,” Martorano said. “That’s it.”

  Casabielle instantly looked up from his notes. “You’re honest?”

  “Yes.”

  “You are an honest man?”

  “I try to be.”

  An honest man—this might be the crack that Casabielle had been probing for. Now the lawyer had to decide which of the twenty murders to use to pry some holes in Martorano’s testimony.

  He picked Richie Castucci, a middle-aged hustler from Revere, who Martorano had shot in the head in Somerville in 1976. Castucci died after the Hill got a tip that Castucci was an FBI informant. Castucci had told the FBI where two fugitive Winter Hill mobsters, Joe McDonald and Jimmy Sims, were hiding out in New York City. Zip Connolly had been convicted in Boston of tipping off Whitey Bulger that Castucci had given up McDonald, but that was something the Florida jury hadn’t been told. They also hadn’t been told at the time of the Castucci murder that Joe McDonald had been on the FBI’s Ten Most Wanted List.

  When the Hill decided to kill Castucci, they had owed a New York bookie $150,000 in lost football bets. Castucci was collecting for the New York bookmaker.

  Just after Christmas 1976, the Hill called Castucci and told him to come over to the mob’s headquarters in a garage on Winter Hill to pick up a down payment of the money they owed the bookie in New York. It was a two-birds-with-one-stone deal: by killing the informant, they were also canceling the six-figure debt to the Mafia-protected bookie in New York.

  If Casabielle was going to undercut Martorano’s testimony, the Castucci murder was as good a place as any to start. Casabielle’s strategy was to keep hammering that one word to the jury: honest.

  “When you lured any of the victims that you shot and killed,” he asked Martorano, “were you being honest with them?”

  “Well, I didn’t think so at the time.”

  “I see. When you told Mr. Castucci to go to an apartment with the $60,000—”

  “I thought you were talking about here,” Martorano interrupted. “I’m telling you that’s true.”

  Casabielle shook his head. “But your statement is, you are an honest man. You didn’t qualify that by saying, ‘I am an honest man today.’ You qualified it by saying, ‘I am an honest man.’ So let’s explore that.”

  “Yes,” said Martorano, warily.

  “When Mr. Castucci met with you at the garage to pick up his money, did you tell him you were going to shoot him in the head?”

  “No, I lied to him and then shot him in the head.”

  “So you weren’t honest then?”

  “No, I was honest to someone else.”

  “So it’s okay to lie to somebody, shoot them in the head, and you can justify that by being honest to some other person?”

  “Usually if somebody gets killed,” Martorano explained, “somebody gets helped.”

  “Who was helped by killing Castucci?”

  “Joe McDonald felt better. I felt better. I felt better at the time. Whitey and Stevie felt better. Everybody felt better.”

  “So you helped them by making them feel better?”

  “I killed a rat.”

  “So the only reason that you killed someone you know, like Mr. Castucci, is because it made you feel good.”

  “No, it was because he was an FBI informant.”

  The unmentioned irony, of course, was that two of the Winter Hill mobsters who “felt good” about Castucci’s murder, Whitey and Stevie, were themselves FBI informants—“Top Echelon,” as the feds described them. The third Winter Hill gangster who felt good, Joe McDonald, had already become so suspicious of Whitey and Stevie that he refused to meet with them while he was on the lam.

  And there was another, larger irony—Johnny Martorano, lifelong hater and exterminator of any rats that he came across, real or imaginary, was now himself a witness for the government. But whenever Martorano was asked now about how he could hate rats and yet testify against his former partners in crime, he always had the same answer. He would mention Judas, the faithless apostle, and how the nuns at St. Agatha’s parochial school in Milton back in the early 1950s had drummed into him that there was no worse person in the Bible, Old Testament or New, than Judas Iscariot, who sold out his Savior for forty pieces of silver.

  Whitey Bulger and Stevie Flemmi—what were they in their own way but Judases who had sold out their friends, and for considerably more than forty pieces of silver? Johnny Martorano knew better than anyone that he was no saint, but he felt comfortable describing Whitey and Stevie as Judases. It wasn’t a hard decision to turn on them—it was his obligation, dammit. Sure, sometimes when he suggested that he was doing something noble now by testifying against the crooked FBI agent, he’d get ripped in the Boston newspapers, or by Zip’s lawyers, but Johnny Martorano knew one thing.

  The nuns at St. Agatha’s would have understood.

  “You can’t rat on a rat. That’s the way I see it.”

  * * *

  JOHNNY MARTORANO looked dapper on the witness stand. He was wearing one of his trademark double-breasted pinstripe suits. After his arrest in Boca Raton in 1995, his common-law wife had put all his clothes into storage for him, and after his release from prison in 2007, he’d had them shipped north to Boston.

  The jury couldn’t see them, but Martorano was wearin
g the most expensive shoes in the courtroom: $700 alligator loafers, custom-made, imported from Italy. In the old days, Johnny would drive across the state to Sarasota, to buy them from a high-end haberdasher, a friend of his. He always paid cash.

  Johnny had always tried to dress appropriately—in the gang’s garage in Somerville, he had favored leather jackets, like Whitey and Stevie. But in his nightclubs in Boston, Johnny wore suits—the police reports sometimes mentioned his meticulous taste in clothes. Cashmere in the winter, silk during the warmer months. His suits he’d buy wherever he could—Filene’s Basement or the swanky Louis of Boston, it didn’t matter to him, off the rack was fine as long as they were properly tailored.

  It was in the accoutrements and the accessories where Johnny Martorano tried to make his fashion statements. For close to twenty years, he’d worn a five-carat diamond pinkie ring, a gift from “the boys” in the gang. But shortly before his arrest in Boca Raton, he impulsively took the ring off his finger and handed it to a fellow fugitive from Boston who was short of cash. Johnny told him to pawn it.

  “I liked the kid,” Johnny Martorano would explain later.

  It was all about the lifestyle. Johnny understood that the Miami and Boston reporters covering his testimony would routinely if imprecisely identify him as a “hitman,” as if any other kind of person could have survived—let alone flourished—in the treacherous Boston underworld of the 1960s and 1970s. But even in those bloody years, there had been another Johnny Martorano—the affable nightclubber, the connected businessman whose first wedding the lieutenant governor of Massachusetts had attended.

  Martorano’s trade—the rackets—bankrolled a lavish lifestyle. He went to Vegas every other month to gamble. Staying at the top hotels and watching the best floor shows, Johnny Martorano was a high-roller, and the casinos comped everything. In the winter, he would fly to Miami to enjoy the beaches and to bet on the horses at Hialeah. He was a ladies’ man. Everyone in his circle knew he had shady business connections, but he was loyal, friendly, quick to pick up a check, and invariably left a big tip. He was fun to be around.