Legends of Winter Hill: Cops, Con Men, and Joe McCain, the Last Real Detective

by Jay Atkinson

  Dennett coined the term slow walking after an old con where he followed half a block behind the mailman, clipping the welfare checks. The idea was to avoid rushing the play by talking or walking too fast, keeping it cool and natural to put the sucker at ease. One time Dennett and Black Jimmy sent a rookie, a twenty-year-old kid who wasn't too bright, to collect the envelope. From a parked car they watched the kid approach the sucker with a flurry of nervous tics. When the envelope came out, the kid grabbed it and sprinted across the parking lot and down the main road.

  Dennett and Jimmy caught up to him and opened the door so the kid could jump in. “I got the money,” he said, flourishing the envelope, his eyes glazed with adrenaline.

  “What the fuck are you running for?” asked Dennett. “The name of the game is slow walking.”

  In the crudest form of the game, Black Jimmy might get away with a few grand. But what had attracted the Winter Hill gang's attention was the size and frequency of the hits Jimmy was making. Adding the Cowboy to the crew brought a whole new dimension to the con. He was a big man, six foot three and 230 pounds, with a size fourteen shoe. (Black Jimmy used to tell the Cowboy to tiptoe up on the suckers; his flapping feet would scare them away.) In the latest permutation of the slow walk, the Cowboy, dressed in suit and tie, would go into the electronics department at Sears and ask to see the manager. Hale and hearty, he would slap the man on the back and say that he represented the Ramada Inn and that it was the manager's lucky day: the chain wanted to buy fifty entertainment units for one of its hotels.

  That's just great, the manager would say.

  “Listen, I gotta couple of my people coming in this afternoon to finalize things,” the Cowboy would say. “Let me borrow your office for a half hour.” He'd explain that he needed a quiet place to fill out the paperwork.

  Later that day, the Cowboy would lead a sucker into the mall. Somewhere along the way a bartender who had been slipped a hundred bucks would call out, “Hey, Bob, how's things over at Sears?” Farther along, the Cowboy would stop outside a boutique and tell the sucker, “Wait here a second. See that girl in there? I like her sister.” Then, out of the sucker's earshot, he'd go inside the store, smile at the girl, say something funny, and ask her where Sears was. The salesgirl would laugh and point and the sucker would think that she and “Bob” were discussing her sister.

  On a big hit, Al Forzese would be hanging around the men's wear department, dressed in a nice shirt and slacks and wearing a phony I.D. badge. He'd wink at the Cowboy and mention that he loved his new TV and wanted another one. See me later, the Cowboy would say.

  The Cowboy and the sucker would walk into the manager's office, and there would be White Jimmy, who had slipped inside at the last moment. Posing as the manager in his well-tailored suit, White Jimmy would tell the sucker that he had some excess inventory and would be willing to make a nice side deal— he'd even throw in the warranties. Then White Jimmy would call Black Jimmy at a pay phone and pretend he was talking to the warehouse, and a few seconds later Billy Dennett would appear in his floppy gray shipper's vest and it would be all over. The sucker would hand over an envelope filled with ten, fifteen, twenty thousand dollars, and White Jimmy would tell him to drive around back and he'd get his television sets.

  As soon as the sucker left, the crew would split up, head for the exits, and disappear. On a good day, they'd work a couple of hours and net up to five thousand dollars apiece. Everyone would go away happy, except the sucker. And he had very little recourse: he couldn't go to the police and say, “I was going to buy some stolen TVs that didn't exist and I got ripped off.”

  Black Jimmy was a student of human behavior, a genius really, and in a short time he and his crew were beating suckers for even larger amounts of money. One of their best scores came on the vacuum cleaner scam. White Jimmy, posing as a district manager for the Howard Johnson restaurant and hotel chain, approached the Kirby Vacuum Cleaner Company and said that HoJo's wanted to change their entire system over to Kirby's. In advance of this, White Jimmy had visited the coffee shop at the local HoJo's, got friendly with the waitresses, spread a little money around on tips, and told the staff that his name was Mr. Parker. When he returned to HoJo's with the Kirby salesman in tow, everyone knew and liked him, and the sucker had no trouble believing he was the manager.

  Mr. Parker told the Kirby salesman that if his initial order panned out, he'd go through this dealership for a nationwide buy. To fill HoJo's order, which was a rush, the Kirby salesman collected fifty units and drove them over to Howard Johnson's in a company truck. Clad in overalls, Black Jimmy and the Cowboy unloaded the vacuums while White Jimmy took the salesman into the coffee shop. There “Mr. Parker” was greeted by name and treated to a bevy of smiles.

  The two men sat down in a booth near the exit, and Mr. Parker asked one of the waitresses, a girl named Tammy, which items on the menu looked good that day. “Get whatever you want,” said Mr. Parker to the salesman. “I'll take care of it.”

  So the Kirby salesman ordered a BLT with French fries and a chocolate frappe and Mr. Parker told him that he was a very smart man indeed as the HoJo frappes were excellent. Meanwhile, Black Jimmy and the Cowboy had finished loading the vacuums into their own truck and, by a prearranged signal, called White Jimmy in the coffee shop and had him paged.

  “Mr. Parker, your office is on the line,” said Tammy. “They want you to run up there.”

  Telling the Kirby salesman that he'd return in a minute, bringing the thirty-day purchase order with him, White Jimmy strode out of the restaurant. Shortly thereafter he and Black Jimmy and the Cowboy were on their way down the road with fifty vacuum cleaners. Later they heard that the sucker waited for a half hour before approaching the front desk to inquire about Mr. Parker.

  “Who?” asked the clerk. “There's no Mr. Parker here.”

  The Kirby salesman began to cry, and the desk clerk phoned the Boston Police. When the cops arrived, one of them said, “You gave him a truckload of vacuums, wholesale value $450 apiece, and what'd he give you? Nothing.” The cops thought it was hilarious.

  As Black Jimmy expanded his group of cons, he realized that more players in the game meant more risks: Richie Carney had been drinking at a bar called the Forum in Kenmore Square, bragging about a score he had made, when the Bear caught wind of it. Flemmi wasn't sure how the con worked, but he knew Black Jimmy was running it. And there were rumors that Jimmy and Billy Dennett were giving information to the cops on the Flemmis and their associates to keep the heat off themselves.

  The rumors about ratting on the Bear were true. The complicated rules that Black Jimmy lived by allowed him to ring up a score in one arena while informing on the dirty players in another. Meanwhile, Joe McCain, with his active stable of informants, pending arrests, grand jury testimonies, and Herculean caseload, was like the nous of Greek cosmology; he saw most of what Black Jimmy and his associates were doing but intervened only when necessary. Big Joe was willing to ignore the shady activities of bookmakers and con men if they helped him to pinch a violent criminal. His Marshall Street upbringing made him a realist: there were lesser evils and greater evils in the world, and greater and lesser goods. In police work, the greatest good was getting a shooter off the street. Therefore, turning someone like Barboza into an informant made no sense, as the best you could hope for was to trade a stone killer for another killer. On the other hand, Black Jimmy never hurt anyone and was often the source of up-to-the-minute information on the most dangerous crooks.

  Black Jimmy and Joe McCain struck their first bargain when the thirty-year-old flimflam man, straight out of Walpole and still on probation, got in a beef over the wedding ring con. In that game, an actor would walk into a nice middle-class joint, hail the bartender, and say that his wife had lost a diamond ring there the night before. Again preying on the bartender's greed, the actor would offer a five-hundred-dollar reward for the safe return of the diamond, saying he'd come back the next day to see if anything had
turned up.

  A couple of hours later, the second actor would turn up with a paste diamond that looked like the real thing. Claiming he'd found the ring beneath one of the tables, the actor would feign surprise when he heard that there was a reward being offered. “Gee whiz, I could really use five hundred bucks, but I can't stick around,” he'd say. “Tell you what, I'll split it with you. Give me two-fifty from the till, and when the reward comes in, you can keep it.”

  At $250 a whack, it was a pretty short con, but Black Jimmy got pinched on it anyway. Billy Dennett, who was already an informant, introduced him to McCain, and Joe fixed it: restitution of $250, charges dismissed, in exchange for Jimmy's promise to let Joe know if anything big was about to go down on Winter Hill. It was the beginning of a beautiful friendship.

  * * *

  THE NIGHT JAMES “THE BEAR” FLEMMI summoned him to the Pond Café, Black Jimmy had the feeling that something was going to go down, all right: him. Still, he kept his nerve and, with Richie Carney along for moral support, drove across town to erase Flemmi's concern that he might be an informant. It was raining hard, a fine, cold sleet that hung like wires in the sky above Jamaica Plain, when he parked the Buick across the street from the bar and he and Carney sprinted over with yesterday's racing form covering their heads. They stamped their feet on the mat and burst into the crowded, smoky club, shaking off their overcoats and scanning the room for the Bear.

  Black Jimmy cursed himself for not bringing a gun— ehh, not even the Bear would shoot someone in front of so many people. But he felt his luck returning when another wiseguy said that Flemmi hadn't been there all night, and Jimmy signaled to Carney, who was up at the bar ordering a drink: let's go.

  As soon as Black Jimmy and Carney stepped outside, Flemmi appeared in front of them, dripping with rain. “Hey, where're you guys going?” he asked.

  “Nowhere,” said Jimmy.

  “Gimme a ride to the Forum,” the Bear said.

  Black Jimmy didn't want to do it, but he had very little choice. If he wasn't talking to the cops— and he certainly wanted Flemmi to believe that— then there was no reason to carry a gun or refuse the Bear a lift. Playing suckers had taught him to maintain an easy, open demeanor, and never to tip his hand. But James “the Bear” Flemmi was no sucker.

  Black Jimmy tossed his keys to Carney and got in the passenger side; if the shit went down, he figured he'd jump out of the car. The Bear ducked into the backseat and moved over directly behind Jimmy. Carney started the engine with a roar, and they drove off.

  In the backseat Flemmi was uncharacteristically silent. But as Jimmy wondered what to do next, he heard two metallic clicks. Glancing back, he saw that the Bear held a silver-plated .32 down by his ankles and had drawn the extractor back, chambering a round. Jimmy leaped over the seat, clamping both hands over Flemmi's as they wrestled for the gun. Driving along May Street at thirty miles an hour, Richie Carney looked over his shoulder at the two combatants, unlatched the driver's side door, and jumped into the street and tumbled away.

  The Buick careered along the shiny thoroughfare with no one at the wheel. Snarling and pumping his elbows, Black Jimmy braced his feet against the door and tried to wrest the pistol from Flemmi's grasp; the Bear leaned down and bit Jimmy's finger to the knuckle, and at that instant, the gun fired twice. One round lodged itself in Flemmi's right shoulder and the second bullet creased the top of his head and passed through the rear window. Then the Buick struck a parked car, jumped the curb, and piled into an oak tree, springing open the passenger side door.

  Dazed, Black Jimmy climbed out of the backseat into the pouring rain. Flemmi groaned from inside the Electra, crawling over the floorboards as he searched for the gun. Taking a last look at his beautiful new car, its fender crumpled and steam whistling through the grille, Jimmy shed his tattered sport coat.

  And he ran.

  TEN

  The Confidence Man

  RAIN FELL FROM THE DARKENED SKY in a great pixilated mass. Dashing between two houses, Black Jimmy lost his right shoe, tripped, lurched like a drunken man, and kept on running; climbing over an alley fence, he tore his pant leg, jumped onto the cinders, and went limping in the direction of Hyde Park. He imagined that Jimmy Flemmi, bleeding from his wounds, was chasing him armed with guns, knives, and a hatchet. Stumbling along, he pictured the Bear driving his battered convertible, its headlights broken, searching for him block by block.

  The streets were empty in the rain. Finally Black Jimmy turned into a more cramped neighborhood and ran into a tenement and began pounding on doors. “Help, I've been robbed,” he said.

  On the third floor a man wearing an undershirt opened his apartment door. Inside the man's wife and two young children were sitting in the shifting light of a television.

  Gasping for air, Jimmy asked to use the telephone, and the man pointed to the kitchen. Black Jimmy pulled out a slip of paper and dialed the number that was printed on it and Joe McCain answered.

  “Joe, someone's trying to kill me,” Jimmy said. “Can you come and get me?” He covered the phone and asked the man's address. “I'm at eleven Paul Gore Street in Hyde Park.”

  McCain wanted to know what had happened, and who Black Jimmy had been with. “I can't talk on the phone,” said Jimmy. “I don't want to scare these people.”

  Twenty minutes later, Joe McCain arrived at the tenement and then drove his passenger to the Holiday Inn across from Mass General. On the way Black Jimmy told McCain about his fight with the Bear and how Flemmi suspected that he was cooperating with the police.

  “Why the hell did you go there?” McCain asked.

  “I didn't want a guy like the Bear to think I was talking to the cops,” said Black Jimmy.

  McCain and a Secret Service agent named Dave Lee, who was investigating Flemmi on a counterfeiting charge, questioned Black Jimmy for over an hour. The con man had two options: either go into protective custody and testify against the Bear on attempted murder charges, or handle everything on his own.

  Dry and warm and bolstered by a couple shots of whiskey, Black Jimmy began to speculate about going home; perhaps he could talk his way out of this and wouldn't need Joe McCain's help after all. He wondered aloud if Flemmi really had tried to kill him, or whether he had overreacted at the sight of a gun.

  “I think I can square this away,” said Jimmy. “Me and the Bear go way back.”

  Just to be sure, Joe McCain had four uniformed cops meet them outside the hotel, and accompanied by this escort, he and Dave Lee drove Black Jimmy to a phone booth near the Somerville incinerator. It was well after midnight when McCain put a “zinger” on the telephone and Jimmy called the Bear's number and asked whoever answered to have Flemmi call him back as soon as possible.

  McCain and Black Jimmy waited on the corner of Joy Street in the rain. Twenty minutes later, the phone rang and Jimmy picked it up.

  “You stupid motherfucker,” said the Bear. “I'll cut your fuckin' head off.”

  Jimmy hung up, his face gone pale. McCain, who had been listening through a tiny earpiece, acted like nothing unusual had occurred. “Do you still think you can resolve this, Jimmy?” he asked.

  Black Jimmy was ready to faint. “I'll testify,” he said.

  McCain winked at Dave Lee. “Are you sure, Jimmy? Because we'll drop you off, if you want.”

  “Stop fucking around, Joe,” said Jimmy.

  They stashed Jimmy in the hospital ward at the Charles Street jail, and then McCain and Lee arrested James Flemmi for attempted murder.

  Three months later, Flemmi went to trial. Assistant District Attorney Jack Zalkind represented the government and Joe Balliro was Flemmi's defense lawyer. Balliro's strategy was to parade every known criminal to the stand, each of them swearing that he knew Black Jimmy and that Jimmy had been threatening to kill the Bear. At the very worst, Balliro argued, the incident in Jamaica Plain was a couple of tough guys who were trying to kill each other. In fact, James Flemmi had suffered the only real inj
uries in their fight— the bullet wound to the shoulder and a cut on his head. Balliro also noted that Black Jimmy had a criminal record, and that several “reliable” witnesses had stated Jimmy was going around that night with a gun in his belt saying, “Where's the Bear?” (This was so improbable that Balliro's comment drew snickers from the gallery, which contained a large number of mob types.) According to Balliro, James Vincent Flemmi was the victim here, not the perpetrator.

  Zalkind argued that if Black Jimmy had been out Bear hunting as the defense had argued, he would have taken a bear gun, not a little bitty .32. Additionally, investigators had learned that Flemmi had gone to a man named Dr. Chin and had the bullet removed in exchange for a bundle of cash, the typical practice of North End wiseguys and not the action of an innocent victim. But in the end, it was Black Jimmy's testimony and dumb-as-a-fox Joe McCain who turned the tide for the prosecution. In reconstructing the struggle for the gun, big Joe reasoned that Black Jimmy's hand was on the outside— otherwise, Flemmi couldn't have bitten his finger, which would've been protected by the trigger guard. Therefore, it was Flemmi who had brandished the .32. With that, the government rested its case.

  During a recess, Joe McCain and Dave Lee and Leo Papile and a bunch of other cops were milling about in the hallway. Across from them were Joe Balliro and Flemmi, who was out on bail throughout the trial. Glowering at McCain, the Bear said, “Oh yeah. Six-three-five-nine-three-nine-nine,” reciting the McCains' home number. Joe went right after him. Havoc broke loose, as Papile grabbed McCain by the throat and two other cops helped pull him away from Flemmi. “Don't fuck with me,” said McCain, pointing at the Bear.

  The jury began deliberating that night, with a verdict expected in the morning. Black Jimmy remained locked up in protective custody. Throughout the trial, his wife had received telephone threats. That night Black Jimmy thought he saw the mobster Frank “Cadillac” Salemme outside the jail and refused to go near any windows, thinking Salemme was there to kill him. When Joe McCain heard about it, he visited Jimmy's wife to reassure her that she and Jimmy were receiving police protection and would continue to do so. Then McCain went over to the Charles Street jail, bringing sandwiches and coffee, and he and Jimmy sat and talked for hours.