The Brothers Bulger

How They Terrorized and Corrupted Boston for a Quarter Century


By Howie Carr

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The riveting New York Times bestseller by award-winning columnist Howie Carr–now with a stunning new afterword detailing Whitey Bulger’s capture.

For years their familiar story was of two siblings who took different paths out of South Boston: William “Billy” Bulger, former president of the Massachusetts State Senate; and his brother James “Whitey” Bulger, a vicious criminal who became the FBI’s second most-wanted man after Osama Bin Laden. While Billy cavorted with the state’s blue bloods to become a powerful political force, Whitey blazed a murderous trail to the top rung of organized crime. Now, in this compelling narrative, Carr uncovers a sinister world of FBI turncoats, alliances between various branches of organized crime, St. Patrick’s Day shenanigans, political infighting, and the complex relationship between two brothers who were at one time kings.

As the film Black Mass, starring Johnny Depp as Whitey Bulger, hits theaters, take a deeper dive into the story of the Bulgers, and their fifty-year reign over Boston with Howie Carr’s The Brother’s Bulger.


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First, I'd like to thank my beautiful wife, Kathy, and our three lovely daughters: Carolyn, Charlotte, and Christina.

Without the help of everyone at the Boston Herald, where I have worked for so many years, I could never have written this book. Thanks especially to publisher Patrick Purcell, editorial director Ken Chandler, former editors Andy Costello and Andrew Gully, and to all the reporters, photographers, columnists, and editors going back to the days of Hearst, especially Joe Heaney. My gratitude as well to the Herald's peerless library staff, especially, in recent years, Al Thibeault, John Cronin, and Chris Donnelly.

Thanks to my literary agents, Larry Moulter and Helen Rees, and to my editors at Warner Books, first Rick Horgan, now at Crown, and later Les Pockell. Also, thanks to my "book doctor," Jeff Kellogg, whose assistance was invaluable. My researcher, Stuart Horwitz, also did fine work, obtaining interviews from people who might not have spoken to me, and he always persevered, despite the occasional brush-off.

Also, I owe much to some reporters at the Boston Globe with whom I have worked (and competed against), although I won't name them for fear of damaging their future prospects. But I must single out two people who no longer work on Morrissey Boulevard—former Globe staffers Dick Lehr and Gerard O'Neill. In many ways their 1999 book Black Mass lit the path for others to follow. In particular, their work on the 75 State Street scandal, first for the newspaper and then in their book, cannot be overpraised.

The information provided to me in the preparation of this book came from more people than I could ever hope to list, even if they wanted me to, which I believe most of them don't. They know who they are, and they know how much I am in their debt. Thanks to one and all, especially to the survivors, and that is not too melodramatic a word to use when considering what so many people involved in this sordid story have endured over the past forty or so years.

I would also like to express my appreciation to, in no particular order, and for various reasons: Chris Lydon, Nancy Shack, Larry Bruce, Michael Goldman, and Jon Keller, and among those who are now gone, Jerry Williams, Paul Corsetti, Jackie McDermott, and Fred Langone.

If I have neglected to mention anyone by name who wanted to be so identified, I apologize. Better safe than sorry, even now.


BILLY BULGER WAS ON THE spot. This time he couldn't take the Fifth Amendment when a congressman asked him if he knew where his fugitive gangster brother was hiding out, with a $1 million bounty on his head.

It was June 19, 2003, and the sixty-nine-year-old president of the University of Massachusetts was sitting in a packed hearing room in the basement of the Rayburn Office Building in Washington, D.C. For six months, ever since he'd stonewalled the House Committee on Government Reform in Boston, William Michael Bulger had called in every chit, pulled every string, to prevent this moment from arriving.

But the reality was that despite his $359,000-a-year salary, Billy Bulger was no longer the most powerful man in Massachusetts politics, and he could not defy Congress.

His brother James—better known by his nickname of Whitey—had been on the lam for more than nine years now. He was on the FBI's Ten Most Wanted List, charged with nineteen murders, and two years earlier his wanted poster had appeared briefly in the film Hannibal. But Whitey hadn't actually been seen in the United States since 1996, and he was slowly making his way into the pantheon of vanished legends—Ambrose Bierce, D. B. Cooper, Jimmy Hoffa, Judge Crater…

Billy had bought a new suit for his appearance before Congress. It was from Brooks Brothers on Newbury Street, to Billy the epitome of upper-crust Yankee respectability. Everyone back in Boston would be watching the C-SPAN feed that was being broadcast on every major TV station in the city.

The committee chairman was Tom Davis, a Virginia Republican, Amherst College '71, and Billy had tried to play the Amherst card with him—hey, can't we work something out? In Boston, they had negotiated over a closed-door hearing—no cameras, no damnable reporters. But word had leaked, and now Davis was gaveling the public hearing to order.

The chairman asked Billy if he wished to make a statement before the questioning began. Billy looked down at a prepared text, which had already been distributed to the press.

"I now recognize," Billy said of his brother, hesitantly, without a trace of his fabled cockiness, "that I didn't fully grasp the dimensions of his life."

It was a far cry from what he'd proudly told newspaper reporters of his brother in 1988: "There is much to admire."

Billy was now immunized—nothing he said could be used against him, unless he lied. But he could no longer invoke his Fifth Amendment privilege against self-incrimination. He was faced with a Clintonian dilemma, and there was only one way out. He would have to… not remember.

"I am particularly sorry," Billy continued, "to think that he may have been guilty of some of the horrible things of which he is accused."

About the allegations made against his older brother, Billy had written in his memoirs seven years earlier: "I am confident much of it has been circulated as an oblique political attack on me. I know some of the allegations and much of the innuendo to be absolutely false."

But that was before the Massaschusetts State Police recovered six bodies, including those of two twenty-six-year-old women, from the shallow graves Whitey and his underworld partner, another serial killer named Stevie Flemmi, had dug on public property in and around Boston. In his memoirs, Billy had never mentioned that Stevie Flemmi was a pedophile, or that Flemmi's parents had lived next door to him since 1980. Nor did he inform his readers that Flemmi often spent the night at his parents' house, across the courtyard from Billy, and that most Sundays, Whitey and Stevie huddled at the Flemmis' house with the FBI agents they had bribed with cash, jewelry, and wine.

"I do still live in the hope that the worst of the charges against him will prove groundless," Billy Bulger read. "It is my hope."

But the congressmen would have none of it. Although the committee was ostensibly investigating almost forty years of corruption in the Boston FBI office, today's hearing was about the Bulger brothers—Whitey and Billy. Even the Massachusetts Democrats on the committee, playing to the vast television audiences watching in New England, would take their shots. But the most relentless congressman was Republican Dan Burton, the former committee chairman who had pursued Billy for more than a year. Dan Burton was from Indiana—a "jerkwater state," as Billy would have described it at one of his annual St. Patrick's Day breakfasts in South Boston. This was Dan Burton's show, and he couldn't be cajoled or threatened. If Burton had been from Massachusetts, Billy would have known which buttons to push. But he was from Indianapolis, and Billy Bulger was now under oath.

"Mr. Bulger," Burton began, "what did you think your brother did for a living?"

Gone was the glib, gavel-wielding boss of Massachusetts politics. "Well, I know that he was for the most part," Billy stammered, speaking uncharacteristically in sentence fragments. "I had the feeling that he was uh in the business of gaming and and uh…" He paused. "Whatever. It was vague to me but I didn't think, uh—for a long while he had some jobs but uh ultimately uh it was clear that he was not uh um being um uh you know he wasn't doing what I'd like him to do."

Billy's biggest problem was a phone call he'd received from Whitey in January 1995, just after he'd fled Boston. Though Billy was an attorney, an officer of the court, he had told no one in law enforcement about the conversation until 2000, after one of Whitey's underlings had disappeared into the Witness Protection Program. The feds had called Billy before a grand jury, laying a perjury trap, but much to the feds' chagrin, he'd admitted receiving the call. Angry and frustrated, someone in the U.S. Attorney's Office had leaked his testimony to the newspapers.

"I expected I would receive a call," Billy said, tentatively, mixing tenses. "That was his request. I am sure he would like a private conversation."

Billy had had six months to prepare his answers, but he still couldn't come up with the witty, cutting responses that had so long been his trademark in state politics. In fact, Billy sounded as tongue-tied as one of his majority leaders.

"I never thought we'd still be—that there would not have been a resolution of it. Ordinarily in these cases—"

—the cops catch the guy. Billy stopped himself before he actually said it. The only other time Whitey had been a fugitive, from a bank robbery indictment in 1955, he'd lasted only three months on the lam before the FBI collared him. But in 1994, Whitey was forty years wiser, and perhaps $40 million richer.

"So the tone of it," Billy said, "was something like this: He told me, uh, don't believe everything that's being said about me. It's not true."

But of course it was true. All of it.

"I think," Billy said, slowly, "he was trying to give me some comfort on that level and he—I don't know…" Billy paused, as everyone stared at him. "I think he asked me to tell everybody he was okay and, uh, and then I told him, well, we care very much for you and um, we're very hopeful. I think I said I hoped this will have a happy ending. At the time there was no talk of the more terrible crimes."

It was December 23, 1994, the day that Whitey Bulger vanished. He had always assumed that it would come to this, so in 1977 he had begun constructing a new identity for himself. The most powerful organized crime figure in New England was about to turn into "Thomas F. Baxter."

When the cops got around to searching his condo, and his girlfriends' houses, they would find an Irish passport, as well as how-to books about living on the lam. There were almost as many of them as there were World War II books and videotapes. Whitey was obsessed with Nazis, so much so that in 2004 the feds would consider staking out the sixtieth anniversary commemorations of D-day in Normandy, hoping to catch him traveling on a European Union passport.

The cops would also find his diaries. He'd begun putting his thoughts down on paper a lot just before he left. He would sit at the kitchen table in his condo in Quincy, where he'd replaced the sliding glass door that led to his back patio with a bulletproof steel plate. Night after night, he'd write in his old-fashioned Palmer-style longhand about the LSD experiments he'd taken part in while in prison in Atlanta in the late 1950s.

"It's 3 a.m. and years later, I'm still effected [sic] by L.S.D. in that I fear sleep—the horrible nightmares that I fight to escape by waking, the taste of adrenalin[e], gasping for breath. Often I'm woken by a scream and find it's me screaming. I later read while still in prison that LSD can cause chromosome damage and birth defects—that one article determined for me that having children was too risky."

Would a jury buy it? That Whitey Bulger cared about children? Whitey hoped he never had to find out.

It was late afternoon, and as he drove toward downtown Boston, the Christmas lights twinkled in the projects and the three-decker houses of South Boston where he'd spent his entire life, except for a few years in the air force, and later almost a decade in federal prison, in Lewisburg, Atlanta, Leavenworth, and Alcatraz.

About to be indicted again, for the first time in thirty-eight years, Whitey would disappear, until he could put the fix in, the way he always had. Something always seemed to happen when the law got too close to Whitey—wiretaps would be compromised, bugs discovered. Cops hot on his trail would find themselves demoted or transferred. Witnesses would disappear, or recant, or forget. Or Whitey would receive a phone call moments before the police raided a warehouse stuffed with marijuana that just happened not to be under his protection.

Surely something could be worked out this time too. And if not, "Tom Baxter" would enjoy his golden years, another retired gentleman on the road with his lady friend.

Beside him in the front seat of the Grand Marquis was his most trusted underling, Kevin Weeks, age thirty-seven. Weeks had been with Whitey almost from the day he graduated high school in 1974. Like all of Whitey's closest associates, Weeks called him "Jim." Over the years he'd helped Whitey plan his eventual flight. They had beepers, and code words, and now Kevin would be Whitey's eyes and ears in the Town, as they referred to South Boston.

In the back seat sat Theresa Stanley. At fifty-seven, she was the oldest of Whitey's girlfriends, and she preferred a more traditional, lace-curtain Irish phrase to describe their relationship. She "went with him," and had since 1965 when he was a thirty-six-year-old ex-con, fresh out of Leavenworth, and she was a single mother of four young children.

Theresa had been looking forward to Christmas this year. She and Whitey had just returned to Boston after a lengthy trip to Europe, a dry run for the journey they were about to embark upon. Whitey had made good use of his time, renting safe-deposit boxes in banks in Dublin, London, and Venice, before they finally returned home, at Theresa's behest, after Thanksgiving.

On this day, Whitey and Theresa had been planning to drive to Copley Square and finish their Christmas shopping at Neiman Marcus. But around 4:00 p.m., dusk on one of the shortest days of the year, Kevin Weeks had beeped Whitey and asked where he was.

"Theresa's," Whitey said. "We're just going out."

"We need to talk," Kevin Weeks said. This was one of Whitey's rules: Never talk on the phone if you didn't have to, and if you had to, always keep it vague.

Weeks had gotten a tip from John Connolly—"Zip," as Whitey called him—about an hour earlier. Zip, a retired FBI agent who'd been raised in the same public housing project as the Bulgers, had been feeding Whitey information for years—about informants, indictments, investigations, and wiretaps. And now, in addition to his FBI pension, Zip had a six-figure job at Boston Edison, compliments of Billy, Zip would always tell his friends while he and Billy both denied it publicly.

Five minutes after Weeks's call, Whitey's Grand Marquis pulled up in front of the South Boston Liquor Mart at the rotary on Old Colony Avenue, the gang's headquarters for the last decade or so.

Weeks hopped in, but said nothing. That was another one of the rules. You didn't talk in the car, not since the Drug Enforcement Administration had put the new door on Whitey's car back in 1985 as part of Operation Beans. It had been yet another attempt to bring down Whitey that had failed after he received a propitiously timed tip.

At sixty-five, Whitey was not the stereotypical elderly driver. Years later, on the witness stand, Weeks was asked how they could get from South Boston to the Back Bay so quickly during rush hour two days before Christmas. Could Whitey make cars magically move and disappear?

"Jim Bulger could make a lot of things magically move and disappear."

Whitey pulled the Mercury into the tow zone in front of Neiman Marcus. Then all three of them—Whitey, Kevin, and Theresa—got out of the car and Whitey told Theresa he'd be right with her. She waited at the entrance to Neiman Marcus, eyeing them nervously, as Kevin Weeks passed on the information he'd received from Connolly, that the indictments had come down, that they were sealed, and that the feds were planning to round up everybody over the holidays—including Whitey, his partner Stevie Flemmi, and Frank Salemme, the boss of the local Mafia.

"Have you told Stevie yet?" Whitey asked.

"I haven't seen him," Weeks said.

"Make sure you tell Stevie."

Whitey called Theresa back over to the car and told her, "We're going away again."

Their first night on the road, Whitey and Theresa checked into a hotel in Selden, Long Island. They would be visiting a cousin of Kevin Weeks's named Nadine, and her husband. Later Nadine and her husband would tell the FBI that they had no idea that they were entertaining a powerful, well-connected mobster. To them, they said, he was just Tom Baxter.

Theresa and "Tom" stayed in Selden for four days, then drove to New Orleans for New Year's, where Whitey registered at a French Quarter hotel using his real name. No need to become "Tom Baxter" if this was all just a false alarm. By January 5, almost two weeks had passed since Whitey had been warned about the indictments, and still nothing had happened. Whitey told Theresa they were going home.

That night Stevie Flemmi pulled away from Schooner's, his son's new restaurant in Quincy Market, with his latest girlfriend, an attractive Asian thirty-five years his junior. Two Crown Vics cut Flemmi's car off and blocked its escape.

A DEA agent dragged Stevie out of the car and put a gun to his head.

"What is this?" Stevie said in disgust. "A grandstand play?" A few minutes later, Stevie's younger brother, Michael, a Boston cop, walked quickly into the L Street Tavern, which would soon become famous in the movie Good Will Hunting. Officer Flemmi saw Kevin Weeks playing cards at a table and asked him if he could have a word with him outside. Weeks threw in his hand, grabbed his coat, and walked outside with Flemmi. The cop told him about his brother's arrest, and Weeks quickly paged Whitey. As usual, Whitey was one step ahead.

"I just heard it on the radio," Whitey said. "I'm turning around."

This time they drove back to Manhattan, where he and Theresa checked into a hotel and Whitey spent the night thinking things over. In the morning they headed west, driving aimlessly—the Grand Canyon, Los Angeles, San Francisco—two aging tourists with an old-fashioned reliance on cash, rather than credit cards. Two weeks later Theresa Stanley told Whitey she'd had enough. She wanted to go home. Or so she testified later.

Whitey drove to Clearwater, Florida, withdrew his "Tom Baxter" documents from yet another safe-deposit box, and drove back to Selden. There "Tom Baxter" traded in his old Grand Marquis for a new one. He needed a new traveling companion too, and he had one in mind. Her name was Catherine Greig, age forty-two, and he'd had her on the string for close to twenty years. She was a twin, divorced from a Boston fire-fighter, an old-time Southie broad like Theresa who knew better than to ask questions, even about her ex-brother-in-law, whom Whitey had murdered twenty years earlier and buried on Tenean Beach in Dorchester.

The feds knew who Catherine Greig was. They'd tapped her phone at least once. They had surveillance shots of her and Whitey, walking her two black miniature poodles, Nikki and Gigi. Whitey was always complaining about those damn dogs, even though he had taken them to obedience school in Clearwater. Kevin Weeks had made it clear to her that she could not bring them along. Not on this trip.

But "Tom Baxter" and Theresa would spend one final night together. On their way back to Boston, they checked into a hotel in downtown Manhattan, and in the room, Whitey turned on one of his favorite shows—America's Most Wanted. He watched, silently, as John Walsh introduced him as the Fugitive of the Week, and ran the blurry 1991 surveillance video of himself at the Massachusetts State Lottery Commission headquarters in Braintree.

The pictures were almost four years old now. Whitey was wearing sunglasses and a white Red Sox cap as he claimed his "share" of a $14.3 million Mass Millions ticket that he had received under murky circumstances.

At the time, strolling into Lottery headquarters had seemed like a lark, but now Whitey saw it for the hubris that it was. For the first time, the cops had video of him. Not that it would matter much—during the next nine years, America's Most Wanted would feature Whitey twelve times, to no avail.

The next day, Whitey and Theresa returned to Massachusetts. Just after dark, he pulled into a restaurant parking lot in Hingham.

As Theresa got out of the car, Whitey told her he was headed for Fields Corner in Dorchester, to meet Kevin Weeks. In fact he was about to drive to Malibu Beach, where Kevin Weeks would deliver Catherine Greig to him.

As for Theresa, she had some nice diamond jewelry she could hock, if times got tough. Or she could go back to being a banquet waitress, if her varicose veins didn't act up. Sooner or later, Whitey knew, the cops would come calling, and she'd give up "Tom Baxter." But then she'd feel guilty, and call Kevin, and Kevin would beep him. With any luck, all this would be straightened out by then, and if it wasn't, he would have a new alias, or two, or three. For that, he was counting on his old friends from Alcatraz.

But right now, he wanted to talk to his brother Billy. In case the feds already had a pen register on Billy's phone, they would use Eddie Phillips's house in Quincy. Eddie worked for Billy at the State House, and the joke was that his most important qualification was that he was one of the few guys in the building shorter than Billy.

Once Whitey talked to Billy, he could get back on the road. Whitey wanted to drive and drive and drive. That's what he'd done when he'd gone on the lam in 1955, and that was still the plan. A year later, when the feds recovered "Tom Baxter's" Grand Marquis, in Yonkers, New York, it would have 65,000 miles on its odometer.

Whitey watched as Theresa got out of the car in front of the restaurant in Hingham, clutching her single suitcase.

"I'll call you," he said.

She never saw him again.

Nine years later, his brother Billy was still being questioned, under oath, about the phone call, by one of the few congressmen of either party on the committee who seemed even slightly sympathetic, Representative Henry Waxman of Los Angeles.

"Where were you," Waxman asked Billy, "when you received the telephone call from James Bulger?" He pronounced the last name incorrectly, as "Bul-gar," rather than "Bul-ger," with a soft g.

"I was in a friend's, an, an employee's home," he said. "I was asked where I would be and I received a call there."

Waxman: "Who asked you where you would be?"

"I don't have a specific recollection," he said. "But the only person it possibly would have been would be his friend, Kevin Weeks."

His ex-friend, now. Weeks had been arrested, finally, in 1999. After less than a month in the federal holding pen in Central Falls, Rhode Island, he had flipped. Overnight his nickname in Southie went from "Kevin Squeaks" to "Two Weeks."

All-powerful a decade earlier, the Bulger gang had scattered to the winds—they were either dead, in prison, on the lam, or under house arrest. Even the youngest Bulger brother, Jackie, had just pleaded guilty to federal perjury and obstruction-of-justice charges involving Whitey's safe-deposit box in Clearwater, Florida. The conviction cost Jackie four months in prison and, at least temporarily, his $3,778-a-month state pension.

Zip Connolly, the Bulger family's personal FBI agent, was in a federal prison in Lexington, Kentucky, until June 2011, unless, perhaps, he could serve up someone else, the way Kevin Weeks had delivered Connolly with his testimony in U.S. District Court.

Now Dan Burton was asking Billy what he discussed with his brother, the serial killer. Billy's response was gibberish.

"I'm his brother," Billy said. "He sought to call me. Or he sought to call me and I told his friend where I'd be and I received the call and it seems to me, um, that is in no way inconsistent with my devotion to my own responsibilities, my public responsibilities as a, well, at that time, uh, president of the Senate. I believe that I have always taken those as my first, my first obligation."

Burton asked Billy if he had offered Whitey any advice. "My brother's an older brother," Billy said. "He doesn't—he didn't—come to me looking for advice."

Four Massachusetts congressmen watched anxiously, awaiting their turns to question Billy. Not so long ago, when he had controlled congressional redistricting, many of these same politicians had flattered him, attending his St. Patrick's Day breakfasts and laughing at his ancient jokes, donating more than generously to his campaign committee. Now they couldn't wait to throw him overboard.

Representative Marty Meehan of Lowell took the microphone now. Before Marty had first run for Congress he had been solicitous enough of Billy's blessing to arrange a formal introduction from one of Billy's dearest friends, a lobbyist. Like everyone else on Beacon Hill, Meehan had considered it imperative to have the imprimatur of Mr. President before he embarked on any endeavor, political or otherwise.

Not that any of that mattered now. Meehan was ambitious, he wanted to run for the U.S. Senate someday, and as a former prosecutor he knew how to draw blood. He asked Billy about the proximity of his house to the Flemmi residence, which the feds had lately taken to calling a "clubhouse" for Whitey's Winter Hill Gang.

"How much distance," Meehan asked, "is there between your house and the Flemmis'?"

"Perhaps from here to the first desk." About fifteen feet, in other words.

"Nothing ever looked suspicious over there?"


"You're aware Debra Davis was murdered next door?"

"Yes." Debra Davis, one of Stevie's girlfriends, had been twenty-six when Whitey strangled her.

Next up was John Tierney, from the North Shore of Massachusetts. He had more questions about Zip Connolly.

"Did you encourage Connolly to attend Boston College?" There was a pause, followed by a sigh. "I may have," Billy said. "I honestly don't recall. I would, um, I was a little older of course and Connolly would be, uh, around, and I, I could very well have."

Tierney: "Did you write a letter of recommendation for him to attend graduate school?"

"I don't believe so." Then Billy's lawyer leaned over and whispered something in his ear.

"Oh," Billy said, nodding. "About the Kennedy School of Government, I am reminded I think I did send a letter over to the Kennedy School."

Tierney: "Mr. Connolly worked on some of your campaigns?"

"I believe he probably did."

The committee counsel brought up the subject of one of Whitey's hitmen, John Martorano, who had already pleaded guilty to twenty murders between 1965 and 1982. Martorano had testified under oath that Whitey once told him that Billy had ordered Zip Connolly to keep Whitey out of trouble.

"He said that?" Billy asked. "And was Mr. Martorano there when I did? Was he present?"

"He understood," the lawyer said, "that you had done that at some point."

"I see," said Billy. "Well, if I ever did say something like that uh, influence him to stay on the straight and narrow, if that's what's meant by it I could well have said it…. I think it's a pretty innocent comment, if in fact I made it. I have no recollection but I don't want to quarrel with that source."


On Sale
Jul 31, 2007
Page Count
368 pages

Howie Carr

About the Author

Howie Carr is the author of two New York Times bestsellers, The Brothers Bulger and Hitman. Before Bulger fled in 1994, Carr was such an implacable foe of the serial killing gangster that Whitey tried to kill him as he left his house in suburban Boston — an incident reported in 2006 on 60 Minutes. Whitey’s younger brother, Billy Bulger, then the president of the Mass. State Senate, publicly referred to Carr as “the savage.” Carr is also the host of daily syndicated four-hour radio program heard throughout New England, and is a member of the national Radio Hall of Fame in Chicago. He won a National Magazine Award in 1985 for Essays & Criticism in Boston Magazine.

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