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Dangerous liaison

In a way, DiSilva felt she had something over some of Flemmi's other girlfirends: She was older, more experienced, and didn't harbor any illusions about their relationship or her place in his life.
By Ralph Ranalli

As she twists the throttle, the burgundy Yamaha Waverunner XL 760 leaps forward in the aquamarine waters of Florida's Intercoastal Waterway, leaving behind an impressive white roostertail of spray. In moments, Marilyn DiSilva is traveling 40 miles per hour, the wind blowing back her chestnut hair and sunshine bathing her smiling, deeply tanned face.

Four curved dorsal fins break the water about 50 yards away; a group of dolphins is making its way up the channel, swimming in perfect unison. "Look at that! Welcome to Florida! Isn't this incredible?" DiSilva yells, slowing down just long enough to point before torquing the throttle wide open again.

Skimming across the light chop, the Waverunner zips past pelicans perched on concrete pilings, pastel-colored waterfront homes, and a seemingly endless parade of small beach-resort towns. Restaurants shaped like tall ships are landlocked next to ocean-view motels with names like Ebb Tide and Jolly Roger. The area seems stuck in a Gulf Coast time warp - there isn't a Starbucks or a Gap in sight. Ubiquitous instead are palm-thatched open-air "tiki bars" that look as if they are on loan from the set of Beach Blanket Bingo.

Yet, where others see kitschy fiberglass pirates and pricey trinket shops, DiSilva sees nothing but azure waters, blinding sunshine, and a fascinating display of marine life. "It's become part of me. I've lived in beautiful places - the Arizona desert, Hawaii, Costa Rica," she says, "but I always come back here, because it is the most calm and serene place I know."

She even sees the beauty in stingrays. They're in season in early summer and can sometimes be seen moving en masse, like a big, ominous storm cloud drifting under the water. Mostly, though, they hide peacefully under the sand. Until they get stepped on, that is. It's easy to spot the limping beachgoers who have suffered the excruciating jab of a venom-laced barb; getting zapped by a stingray is almost a rite of passage here.

Yet, Marilyn DiSilva is one of the few people she knows who have been able to wade among the rays without ever being stung. In a way, her whole life has been like that; she always seemed to make her way through hazards unscathed.

There was another time when she was wading in dangerous waters indeed. This 52-year-old jet-skiing, scuba-diving, cigar-smoking woman was once the unofficial mascot of Boston's infamous Winter Hill Gang. The leaders of the gang, James "Whitey" Bulger, Stephen "The Rifleman" Flemmi, and John Martorano, when their combined body count is tallied, are probably the most prolific murderers in Boston history. Authorities suspect them, all told, of killing at least three dozen people, both foes and friends, including two of Flemmi's ex-lovers.

Once upon a time, on the gritty streets of Boston and Somerville, Marilyn DiSilva was Stevie Flemmi's girl - and she has survived to tell the tale.

DiSilva still remembers the look on Flemmi's face that day in late 1978 when she told him she was leaving for good, ending their four-year relationship. She had gone to an apartment in Somerville to drop off the keys to the Cadillac he had given her. She says she had never seen that expression before, his dark eyes hollow, his face contorted with anger.

"If looks could kill, I would have dropped dead. His whole face was in a rage, an instant rage. He couldn't believe I was leaving - like I had slapped him in the face," she says. "It was scary, the one time it took me aback, and I said to myself: 'Wow, maybe doing it this way wasn't a good idea. I could have put the keys in the mail.' But I wanted to do it to his face and at least give him that."

It was only years later that she would hear that Stevie Flemmi was suspected in the murders of two other lovers, Debra Davis and Deborah Hussey, his longtime paramour's teenage daughter. At the time of their confrontation, DiSilva says, she had a feeling that she should get away. During the preceding year, she had become increasingly nervous about her connections with the Winter Hill Gang and the effect it could have on her three daughters.

Later, when she lived on a brackish section of the Weekiwachee River in northern Florida, she would trap crabs and feed them. It was mostly leftovers - lasagna, meatballs, whatever - anything to keep the imprisoned crustaceans from turning on one another for food until she was ready to cook them. In a weird way, it reminded her of her days hanging out at Marshall Motors, the Winter Hill Gang's garage in Somerville. The same foods kept Stevie Flemmi, Whitey Bulger, and Johnny Martorano fat and happy as they sat around plotting their criminal business. "I went from feeding the Winter Hill Gang to feeding crabs," she says.

DiSilva still has a vivid mental picture of the scene at Marshall Motors. A couple of times a week, after seeing her daughters off to school, she would drive to the Winter Hill apartment Flemmi had set up for her and start fixing their lunch, maybe a tray of stuffed shells or manicotti. She would walk the food down the street to the Marshall Motors garage, through the front office, and into the back room, where they invariably sat in the same three ramshackle chairs - Whitey behind an old desk, Stevie in front, and Johnny off to the side.

They would all talk, and eat, then talk some more. In a way, she had a relationship with all three. "I had the intellectual conversations with Whitey, the sex with Stevie, and the fun with Johnny," DiSilva says. The arrangement worked, at least for Flemmi, who was always busy juggling several girlfriends as well as two families - one with his estranged wife, Jeannette, and the one with his companion Marion Hussey.

"You know you're my number one. You know I care about you more," he would tell DiSilva, though she knew it was a lie. "Not that I knew a lot about the others," she says. "But I knew they were there."

There was an undeniable attraction between DiSilva and Flemmi. "The sex part was always good," DiSilva says. In a way, she felt she had something over some of his other girlfriends: She was older, more experienced, and didn't harbor any illusions. Still, she sometimes coveted the perks they got, including Saturday nights with Stevie and exotic Jaguar sports cars. She made do with weeknights, a boat-size Cadillac, and the time she spent with the boys at the garage. "He saw me a lot that way, so he didn't have to take me out," she says. "That's why he set me up with Johnny at night to play."

Last year, Martorano pleaded guilty to committing 20 murders, many of them at the behest of Bulger and Flemmi during the time when the Winter Hill Gang was consolidating its power over the bookmaking industry in Boston. After the deal with the government, DiSilva says, she was stunned to learn that during much of the 1970s, when they were hanging out together, her 300-pound party pal was busy murdering people.

The image of Martorano as ice-veined killer haunts her. She remembers him as a big, smiling, booze-swilling and pot-smoking teddy bear who hung around with a pair of beautiful, raven-haired twin sisters from Denmark and always seemed to have Barry White on the cassette player in his Cadillac. He seemed perhaps the most genial and harmless of the group as they drove around Boston, going to parties or restaurants or to Basin Street South, a nightclub he owned.

Of course, there was probably a lot that went on that DiSilva didn't know about. Her nights, which started after her girls went to bed at her mother's house, usually ended early, she says. At least by the gang's standards, that is.

"I would always make sure I was sober enough or straight enough to go home to my daughters so I could get them off to school the next day," says DiSilva. "By 2 a.m., when I was gone, when the coke came out and all, [the gang] probably had an orgy. If it had ever started when I was around, I would have been out the door. I am not that kind of person."

Much of her time with Stevie and the gang was at Marshall Motors, during the day, when her girls were at school. She would hang with them and laugh and argue with Whitey, the group's resident know-it-all. They sparred about sports, current events, and politics, although Whitey said little about his politician brother, Billy, she says. "He would be sitting at his desk, picking his nails with that knife from his boot," she says. "We used to talk about baseball, a little hockey; they had bets on everything. It was a lot about Southie, how he helped different people. We always talked about the good things he did, bragging."

She loved trying to take the pompous Bulger down a peg or two, prompting him to say to Flemmi: "Listen to her, she's like a [expletive] truck driver. Listen to that trash coming out of her mouth."

Her reply: "[Expletive] you, Whitey. This is how I talk. If you don't like it, then you can leave the room."

"I would be sitting safe in Stevie's lap at the time, and he would be laughing, but then he would nudge me, as if to say, 'Don't push this.' Then I would say, 'Do I look like a truck driver?' And I would prance around a little bit. He'd say to Stevie, 'Why don't you get rid of her?' "

She never thought Bulger meant it literally. Twenty-five years later, after hearing the stories of the two Debbies, she wasn't so sure. Debra Davis, Flemmi's girlfriend of nearly 10 years, disappeared in September 1981. According to the Davis family, Flemmi actually wept in front of them after she had "left" Boston, supposedly with another man. The family never heard from her again.

Police heard stories around the underworld that Flemmi had killed 26-year-old Davis and had buried her body underneath the Marconi Club, a private barroom he once owned in Hyde Park. They eventually searched the basement of the club, which Flemmi had long since sold, but found nothing. Last month, State Police, Drug Enforcement Administration, and IRS investigators working with US Attorney Donald K. Stern's office searched for her remains under the Neponset River train bridge in Quincy. In mid-October, investigators found a body that they believe is Davis.

Deborah Hussey vanished four years after Davis, just before Thanksgiving in 1985. She was the eldest daughter of Marion Hussey, with whom Flemmi had had a relationship for many years, but she was not Flemmi's child. Investigators believe Flemmi was Woody Allen to Debbie's Soon-Yi. Law enforcement sources say that shortly before her disappearance, 26-year-old Debbie Hussey, who had had numerous scrapes with the law, had started telling people she'd had a sexual relationship with Flemmi since she was 14. For a time, the family believed she might have gone to California, but like the Davis clan, they heard nothing more and began fearing the worst. Her remains were recovered last January in a dirt pit near Florian Hall in Dorchester. Marion Hussey has repeatedly declined to talk about her daughter or about her relationship with Flemmi.

A longtime Bulger and Flemmi associate, Kevin Weeks, led investigators to the body. At a plea hearing in US District Court in July, Assistant US Attorney Sam Buell told Judge Richard G. Stearns that Weeks had helped Bulger and Flemmi dispose of Hussey's body. Bulger, according to Weeks, had strangled her.

"I don't know what to think, to hear that these other girls are gone," DiSilva says now. "Was he closer to them? Did they know more than they should have? What was the difference between them and me?"

Flemmi, Bulger, and Martorano have arguably surpassed the likes of New England mob bosses Raymond L. S. Patriarca and Gennaro "Jerry" Angiulo, hitman Joseph "The Animal" Barboza, and the Boston Strangler as Boston's most infamous criminals. Authorities now say the trio were responsible for as many as 36 murders.

Moreover, Flemmi and Bulger's controversial work for the FBI's secret Top Echelon anti-Mafia informant program was exposed after they were indicted for racketeering in 1995. The crafty Bulger fled and is still a fugitive, but Flemmi used his informant status as a defense. In 1998, historic hearings sparked a national scandal as bribery and other misdeeds by the Boston FBI agents who dealt with them were exposed. Bulger and Flemmi's primary handler, former FBI special agent John Connolly, was indicted last month for allegedly tipping them off to other informants who were subsequently murdered.

That's why Marilyn DiSilva still uses her married name, to spare her family some of the notoriety she knows will come of the revelation of her past life with the killers. Some of her relatives, after all, still live in the East Cambridge neighborhood where she grew up, in an apartment over a grocery store. She was educated at St. Francis School, off Cambridge Street. The old church and the nuns who lived in the adjacent convent were the main reason her family remained in the city so long after their friends had moved to the suburbs.

Both of her parents worked, so the nuns agreed to look after the preschool-age Marilyn during the day. For the lack of a better place, they stuck her in classes with children several years older.

Her first boyfriend was a year older but a class behind her when they met just before her graduation from Somerville High School in 1965. They dated while he finished senior year, and she took a job transcribing from a Dictaphone at Liberty Mutual Insurance Co. in Boston. Within six months or so, she learned she was pregnant. Her future was suddenly not her own.

"My family planned the whole thing. They didn't ask me, they just said: This is when the wedding is going to be, this is where you are going to live. Bada-ba, bada-ba," she says. "I cried my eyes out. Oh! I didn't want to marry him. I didn't really even like him."

After the wedding, her husband found work as a machinist at Polaroid while she stayed home. But they were never happy. She married while pregnant with her first daughter and divorced three years later, barely 21, when her belly was swelling with her third. Her girls were so close in age that when she dressed them alike, people asked if they were triplets.

She looks back on that time as a crossroads. She took a job waitressing, first at an Irish bar in Cambridge, then at a place called Chandler's in the South End. Chandler's wasn't much to look at, yet the reputation of its clientele made the place seem bigger than just a long bar with tables and a small dining room in back. It was a hangout for Boston's criminal elite and was half-owned by Howie Winter, who had taken over leadership of the Winter Hill Gang after its founder, Somerville longshoreman James "Buddy" McLean, was assassinated in the late 1960s.

It was at Chandler's that DiSilva met Stevie Flemmi in early 1974. Flemmi had been in exile, on the run from charges in the murder of William Bennett, the brother of one of his criminal ex-partners, and the attempted bombing murder of attorney John Fitzgerald, who represented Joe Barboza, a hitman turned FBI cooperating witness. But now, the charges against Flemmi had been dropped. (His attorney, Ken Fishman, would later claim that it was part of a quid pro quo for Flemmi's work for the FBI.)

The brown-haired hoodlum with the dark, flashing eyes was in the midst of a triumphant homecoming. DiSilva spotted him at a party amid a forest of Dom Perignon bottles. "He was a good-looking guy. He was dark. He was very charming. He introduced himself as Steve," she says. "He talked about a couple of cases that he beat. So now he thought he was invincible."

She was an attractive brunette in her mid-20s sporting tight Gloria Vanderbilt jeans and a permanent attitude. He was 15 years her senior. While DiSilva wasn't that impressed at first, his charm and persistence won her over. "He would start asking about me and all, like, did I have a boyfriend, and at the time I didn't have one," she says. "We started going out, either out for some drinks or we stayed and had drinks and talked."

Their first time together was typical mid-1970s sexual-revolution fare. DiSilva's girlfriend Alexis was dating Nick Femia, a hulking criminal associate of Flemmi and Bulger, and she had an apartment across the street from Chandler's - complete with the requisite dim lighting and beaded curtains. It was a very nice place, DiSilva says, "very suggestive."

She and Flemmi were soon an item. His criminal reputation didn't bother her, DiSilva says. After all, hadn't the charges against him been dropped? "He always said he had nothing to do with it. Then there were the acquittals, and I said to myself: 'Maybe they are setting him up.' I didn't dwell on it, let's say, because I was living good."

Flemmi's generosity impressed her. His first gift was a two-tone blue and white Cadillac. He would regularly pull out a fist-size wad of hundred-dollar bills and peel off a few and say, "Why don't you go buy the kids something."

Then there was the time Stevie and Whitey laid out a spread of jewelry in front of her and told her to pick whatever she wanted. She chose a diamond and sapphire cocktail ring and an antique opal. Looking back, she says, it was probably swag from a burglary, but she was too dazzled at the time to care much. Plus, early on in their relationship, she had adopted a firm policy of making herself scarce when their talk turned to criminal matters. "I would tell him, 'I am leaving the room. I don't want to put myself in that position to have to testify or whatever.' "

Flemmi, Bulger, and Martorano, meanwhile, did their best to downplay their own activities. They insisted, for example, that they had nothing to do with murders or trafficking drugs, DiSilva says. "The North End guys do that," they would say. "I basically thought they were bookmakers," she says. "Powerful bookmakers, sure, but basically bookmakers."

After a while the arrangement at Marshall Motors got comfortable - a little too comfortable for DiSilva. Debbie Davis would bring her sleek Jaguar XKE into the garage for service, and DiSilva would notice how comparatively frumpy her big Cadillac looked. The rare nights she and Flemmi went out took some nagging. They weren't glamour evenings from the gangster movies - no front-row seats to Sinatra or surprise plane rides to Atlantic City. They went mostly to out-of-the-way places where they could be alone and indulge Flemmi's passion for raw foods. On special occasions, they would go to Cafe Budapest in the Back Bay. Stevie never dressed up; he'd usually borrow a blazer from the coatroom. Sometimes after dinner they would stop by Blackfriars, a bar on Summer Street in the financial district co-owned by a friend of DiSilva's, a fast-talking part-time cocaine dealer from Quincy named Vincent Solomonte.

Then a horrible incident at Blackfriars started her thinking that maybe the excitement of her double life as mother and a gangster's girl wasn't worth the risks. One night in June 1978, she told Flemmi she was going to the bar to see Solomonte and Jack "TV" Kelly, a former television news reporter. "Don't go tonight," Flemmi told her, and something in his voice told her to listen. The next morning, she learned that Solomonte, Kelly, and three other men had been murdered, gunned down during an apparent drug money robbery in the restaurant's basement. (Years later, Flemmi insisted to her that he had no idea what was going to happen that night, that it had only been a fortuitous premonition. Yet his associate Nick Femia was always a prime suspect. The case was never solved.)

DiSilva also had begun carrying a .38-caliber pistol. "It's time you got a gun," Bulger had said one day. Bulger, Flemmi, and DiSilva went to a sporting goods store and picked out a blue-gray revolver, which she kept in her handbag.

It was for protection, Flemmi said. She soon realized that he meant his, not hers. She always did the driving, and she began to notice that in certain parts of town, he would slouch down in the passenger seat. "If anyone gets close," he told her, "just pull over and duck down, and I'll jump out."

Flemmi never told her who might be coming after him, but it still worried her. She started noticing cars following hers, then the Boston police sent her a notice that her telephone records had been subpoenaed. "It started getting me nervous," she says. "God forbid if something would happen to me, what would become of my children? I couldn't leave them to my mother and father. I partied and played for all these years, and I wasn't giving them any kind of life. Hanging with these guys, it wasn't getting me anywhere."

The emotional pullback from Flemmi, she says, was not painful. Since she had no illusions about her place in his life, she had dabbled, discreetly, in romance with other men.

"Was he capable of love? Not really, I think. He was a man, a macho Italian man. What they wanted they got. And if they could keep their women all in order, they were OK," she says. "I think that helped steer me away from it, too, because he had others, and I wasn't the sole or main thing in his life. Maybe that's why I'm still here. I didn't get possessive to the point where he was my whole life."

DiSilva and Debbie Davis would sometimes barely miss each other at the garage. When Davis brought her car for service, DiSilva made herself scarce. "I knew enough not to cause a scene," DiSilva says. Davis, however, heard about another woman in Flemmi's life and was apparently not as willing to share him. She found his car on the street in Somerville where DiSilva was living. "All of a sudden I hear a smash. She is banging on the door, screaming, 'I know he's in there. Stephen! Come out of there!' " DiSilva says. Flemmi grabbed his clothes and ducked out the back way, over a fence, leaving DiSilva to deal with the irate Davis alone.

"Now I hear the porch windows smashing, one after the other. So I threw a housecoat on, and I opened the deadbolt. She lunges at me and tore my entire thing off. There I was on the porch naked, and she is going at me. Of course, I am defending myself. I had her by the hair, bent back over the railing, and we're screaming at each other. 'I know he's here!' 'You pig!' " DiSilva's father finally came downstairs and broke up the fight, holding down the hysterical, bloody Davis until the police arrived. The next day, Martorano called DiSilva and asked to see her about "the crazy girl who was after Stevie."

"I am taking her to court. I want her in jail," DiSilva told him when he arrived.

"No, you aren't. We want you to drop the charges," Martorano said, pulling out a cash-filled envelope. "We don't need the publicity. We'll take care of the windows. Just drop the charges and forget about it."

She dropped the charges, but she didn't forget. No man, she vowed, was ever going to make her that crazy.

By the late 1970s, it was clearly time to move on. The Winter Hill Gang shut down Marshall Motors, and most of them (with the exception of Flemmi and Bulger, who were protected informants) were indicted on federal charges of horse-race fixing. Howie Winter went to prison, and her party pal Johnny Martorano went on the lam to Florida.

Hanging with the gang was no future, DiSilva decided, and she had been thinking a lot about the future. First on her agenda was going back to school, so she signed on at Bunker Hill Community College. Though a decade older than most of the others in her class, 28-year-old DiSilva immersed herself in student life. She not only played basketball but was elected chairwoman of the Student Senate. Her major, believe it or not, was criminal justice.

"Isn't that a kick?" she says. "Here I am hanging out with the mob at night, and by day I'm taking criminal justice courses." All of a sudden, the girl who had made C's in high school - staying home on humid days because they made her hair frizzy - was getting A's and B's. Even Flemmi was supportive, although she wonders now whether he was only interested in her becoming a cop so he could have an inside source in law enforcement.

But her love of college was competing with an insistent little voice telling her to get her family out of Boston and away from Flemmi and the gang. The little voice won out. A handful of credits short of her degree, she took her first opportunity - a man she was seeing was moving to Westfield to run a pharmacy, and she decided to go, too, and to bring her girls, who were fast becoming teenagers.

Flemmi didn't take the news well. Yet, for whatever reason, the rage she saw in his face apparently subsided, because they were soon on cordial terms again. Her relationship with the pharmacy manager, however, didn't last. He was transferred to New Jersey, but she refused to uproot her daughters again. She liked their little maroon ranch house and the comparatively peaceful life in Western Massachusetts. And she had opened her own restaurant in Springfield.

On her own again, she occasionally made a few trips back to Boston during the early '80s to see Flemmi. Debbie Davis was no longer around, he said. She had "gone off to Mexico with some businessman." At times, DiSilva even brought a friend along for double dates with Bulger.

One of DiSilva's girlfriends from Springfield, a woman named Barbara who now also lives in Florida, remembers getting a jolt during an evening with Whitey. They were drinking in an after-hours joint, and he pulled out "this big old knife" and began playing with it, "showing off and being macho."

"He seemed like a nice enough person," Bulger's date says. "But I don't like knives. I told him to put it away. He kind of tucked his tail between his legs and put it back." Bulger was once charged with rape in Montana during a stint in the Air Force in the 1950s, but Barbara remembers him as "the perfect gentleman."

After a while, even Westfield didn't seem far enough away from the life DiSilva was trying to leave behind. She finally decided to move to Florida in 1984. She came back once, in July 1985, because her daughter was hospitalized in Boston after a car accident. She met up with Flemmi one last time. They spent an evening together for old time's sake, staying at the Holiday Inn in Somerville, and she had someone snap a rare, grainy picture of them. She would not see him again for 14 years.

In the intervening years, DiSilva has had a lot of time to think back on the relationship and ponder why Stevie let her go, what happened at Blackfriars, and what became of the two missing Debbies. In particular, it nags at her how Debbie Hussey's mother could have missed an affair between her 14-year-old daughter and her companion. "How could she have not known that he was messing with her? Those are the kind of things you think about when you have daughters," she says, shaking her head. "I sent him a picture of my daughter and I once, because it was a good one of me. It makes me sick today. But who knew?"

In October 1998, she had a chance to get some of those questions answered when she visited Flemmi in the Plymouth County jail. It was before Martorano and Weeks had decided to cooperate, and when Ken Fishman and Anthony Cardinale, the lawyers for Flemmi and New England mob boss Francis P. "Cadillac Frank" Salemme, appeared to have a shot at getting racketeering charges thrown out due to Flemmi's long association with the FBI. DiSilva's godmother had died, and she ventured north for the funeral. On a whim, she decided to see Flemmi.

"When he saw me, his face lit up like a light bulb," she says, recalling his words: " 'Oh, my God! Stand up and let me look at you. You look so great. It's great to see you. How have you been? How are the girls?' "

Flemmi said his case looked "really good. I hope I can get out of here soon. Maybe we can hook up." The visit was only supposed to last a half-hour, but the guards let them stretch it into 90 minutes. At one point, Flemmi said he was glad he warned her to stay away from Blackfriars on the night of the massacre.

"Did you know what was going to go on?" she asked.

"No!" Flemmi insisted. "I didn't have anything to do with it."

"Who did?"

Flemmi just mouthed the word "Nicky."

When the talk turned to Whitey, Flemmi became even more circumspect. "He said he was being watched and being listened to, and that he was being very careful," she says. The conversation ended there as the guards finally shooed her away.

They stayed in touch by mail. Last Christmas, he sent a card. "Hopefully in the future I'll explain a few things to you. I am sure they will be interesting," he wrote cryptically, signing only with his initial, "S."

Less than a month later, however, State Police troopers, DEA agents, and Boston police started digging up the bodies of the gang's many victims. Flemmi's legal forecast, which had been looking so sunny, suddenly turned ominous. There was little chance now that he would ever risk explaining a few things to DiSilva.

That only adds to her regret that she never worked up the courage to ask him why he let her go. "Was it because I had children? Or was it because I was ballsy enough to stand up to you and walk away?"

Still, life in Florida is pretty good, she says. She's back in the restaurant business, bartending, where the money is just OK, but she has time to indulge passions like jet skiing and scuba diving. "I thought I would be in a better position or career or in a different life," she says. "But I am very contented right now. I can say I've been there and done that. I was a risk taker, but all my children turned out well, thank God. Now I have four beautiful grandchildren. Even when I walk out in the water with the stingrays, I say, 'Thank you, God. I got through another day without getting stung.'

"I've had a hell of a life, and that's how it turned out."

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