Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down (4 page)

“I appreciate that,” Richie told him.

“You’re a stand-up guy,” said Opie. “And we
appreciate
that.”

Richie knew Caruana was handsome, a real lady’s man with a reputation for cavorting about town. Sal was also Richie’s pal and was over the house a lot, more than he’d known, apparently. It pained Richie to imagine his wife in this compromising way, especially since Opie supposedly had photos and “tin ear” chatter to go along for sound from the wire the Bureau had planted. What he saw and heard changed Richie’s priorities in an instant. Suddenly, getting even with Sal Caruana was all that mattered. More than his bookmaking business, more than his nightclub, more even than his relationship with Whitey Bulger. (For the record, Richie’s wife would later deny the affair in a 2009 lawsuit she filed against the U.S. government.)

“We can take care of Caruana for you,” Opie assured Richie. “Get him out of your life for good.”

“What’s it gonna cost me?” Richie replied.

“Look, we need a favor, there are a couple of guys we’re interested in and we thought you could help us out. We know about your ‘book’ and the action you take from the wiseguys. That’s not our interest. We’re interested in something heavier, and if you’re game, we’ll set some contacts up to make sure you are protected and this whole thing stays confidential.”

“You want me to become a rat.”

“And in return Sal Caruana goes down.”

Richie grimaced, clearly conflicted. “I need some time.”

“How much?”

“I’ll give you a call.”

Opie, hardly put off by Richie’s loose hold on cooperation, once more flashed the photo that supposedly showed Sal with Richie’s wife. Richie grimaced again, lips pursed tightly and his face showing a pained expression.

“You got a deal,” Richie told him.

Opie grinned, counted out five one-hundred-dollar bills, and pressed them into Richie’s palm as a show of good faith. Richie, however, remained unimpressed until the agent peeled off ten more Franklins—that finally got him smiling.

Opie returned the grin, and then took advantage of this moment to tell Richie he wanted him to stay in the bookmaking business and remain as close to the New York mob as he had in the past. The agent opened Richie as a criminal informant whose job would be to report on the criminal activities of his associates and also to divulge information on impending crimes. Richie learned that “subjects” were intended for prosecution while “suspects” were more “persons of interest.” And he took to his new role with the same enthusiasm he brought to his dealings with the criminal targets his handlers were trying to bust. Opie figured it was more about Sal Caruana than the money, and he was always able to stall when Richie started pushing on when the Bureau intended to put Caruana away. In the end, they never did, leaving Caruana out there so Richie would have no choice but to continue cooperating.

In future meetings, Richie was informed by Opie and other agents of the rules and regulations governing the whole FBI informant program as outlined in manuals of administrative operations and procedure and in investigative guidelines. Opie debriefed Richie about his background with the criminals and any arrests or incidents he may have had along the way. Subsequently, Richie furnished personal information so the Bureau could check to make sure he was really cooperating.

Opie and his alternate agent handler, who would serve as Richie’s eyes and ears inside the FBI to alert him of possible danger, began to build a bond that transcended the usual relationships developed with criminals on the street. Hip-pocket informants, who were never officially opened as informants, never got this kind of scrutiny. Others, just cooperating witnesses, fared the same. Richie was given special treatment, quickly becoming a “TE,” a Top Echelon informant who’d report on organized crime and individuals of interest to the FBI.

Richie’s status as a bookie served him well here because it made him innocuous, just a real friendly guy who took bets and lay-offs on gambling and never harmed anyone. Richie didn’t know it, but he was also given a number symbol that protected his identity inside the FBI as well as outside, when his information was furnished to the court or other law enforcement agencies. He could feel sure that his identity would never be revealed to anyone outside the Bureau—not to the federal attorneys, the court, or anyone.

Richie heard numerical labels like “137,” “209,” “302” and other classifications that agents discussed among themselves. The 137 was the generic classification for informants; 209 was the report that is filed about the information the informants provide to their handlers; and 302 was the evidentiary report submitted for prosecutorial efforts.

Richie gave his handlers a great deal of information about gambling and scams involving bribery and race fixes. For instance, he explained to Opie that horse talk for fixing a race is called a “boatrace.” The jockeys or their associates get together once in a while to make some money for themselves by pooling their dough and fixing the race in full awareness of which jockey will win. The wiseguys have their own informants who relay the information so that they, too, can turn a profit on a deal. Rumor had it that Richie was the best boatrace guy in the business, information dutifully recorded in his 137 file.

Richie wasn’t worried because he was told that he’d never have to testify. Not once did it dawn on him that his handlers might be lying to him about this, about Sal, about everything. Richie had been all about being liked for so long that he’d bought into his own act. And he’d formed such a tight bond with the agents, especially Opie, that it was inconceivable to him that they were anything but on the up and up. Richie started looking at his handlers the same way he looked at the crowds he entertained at the Ebb Tide. He even came clean about how he got to be where he was, how strong-armed heists had scared him and turned him to the track and gambling, the whole ambiance of which was a better fit for his makeup.

Their bond cemented, Opie would come to Richie with a “shopping list” from time to time, gleaning from him more about past events, new events, and “what are you going to give us now” events. And Richie, ever guilty of wanting to please, was always on the lookout for anything that might help his new FBI pals. He found himself feeling respectable, liking the sense of being on the side of the good guys for a change.

In 1976, on a whim, Opie asked Richie about two murderous muffs from Irish Southie who were on the lam and had made it onto the FBI’s Most Wanted list of top ten fugitives. Castucci knew immediately who he was talking about because they were associates of his: Joe McDonald and James Sims, the very thugs Whitey Bulger asked Richie to stash for him in New York.

Being on the Most Wanted list meant that every agent throughout the United States wanted to capture these guys. But Richie didn’t make his handlers even work hard, stunning the agents when he simply told them where McDonald and Sims could be found. He insisted that Bulger had come to him “out of the blue” to get his assistance in hiding the two killers. Richie told Whitey that a pal of his, formerly in the can at the ACI in Walpole, was a “caretaker” in New York who ran a kind of boardinghouse for on-the-lam criminals. Whitey gave Richie the go-ahead to set up the hideaway for McDonald and Sims, the location of which he nonchalantly furnished to Opie.

McDonald and Sims represented a huge score, a double bubble—two for the price of one. Back at the FBI office, Opie was ecstatic. All of his research and background on Richie was paying off. Many of the agents had scoffed at Richie’s selection as a target for informant development, especially a TE, but Opie’s decision had now been vindicated.

“A happy informant is a productive informant and everyone is then happy!” Opie announced to the agents in his squad bay.

Ironically, Richie even then didn’t push too hard about when the FBI was going to move on Sal Caruana. And, in point of fact, no one from the FBI had any intention to.

“Cheers!” the agents, including John Connolly and John Morris, bellowed in return.

That meant drinks were on Opie and he was more than happy to foot the bill. Thanks to his latest informant, after all, Opie was going to be instrumental in the nabbing of two Top Tens for the Bureau, a potential career-changing accomplishment.

Opie called the New York office of the FBI explaining that he had the inside skinny that would net the fugitives on their turf. The New York agents were thrilled when informed that the Top Tens were holed up in the city. And they were positively ecstatic when they learned that the caretaker in the boardinghouse where the fugitives were hiding was an informant for the New York office.

What a field office’s dream! Opie and the New York agents were glowing over the fact that a couple of Boston muffs, dangerous muffs, had walked into their lion’s den. The FBI in New York had plenty of time to devise a plan to capture these stone killers from Boston. Precautions would be taken to assure that the operation was conducted in absolute secrecy, preventing anyone on either side from screwing it up.

Back in Boston, Richie continued to play both sides of the fence with his usual aplomb. Bulger and Flemmi were treating him like gold and Richie responded in kind by organizing a lucrative boatrace for the Winter Hill Gang. He put together the mother of all horse race scams at Suffolk Downs, calling in his chits from those who owed him. Bulger and Flemmi took part, and word of their participation brought others in as well. Richie even offered his new FBI pals a piece of the action. They refused.

At Boston FBI headquarters, Opie regaled agent John Connolly and his supervisor, John Morris, with his coup. Connolly was a “cock of the walk” agent who had a swarthy complexion and imitated the ethnic dress of the Italians he was committed to jailing; some even quipped that he looked like Richie. Morris dressed more simply and somberly, like a conservative businessman in dark suits, simple ties, and white shirts—in keeping with a silver-haired agent always looking straight ahead. Connolly and Morris were veteran TE developers and had had their share of glory. Like Opie, the other agents didn’t really know which informants Connolly and Morris handled. Unlike Opie, they fumed over the success of others on turf they considered theirs and theirs alone.

Later, over beers, Opie bragged a little too much about his recent success, especially to Connolly, and revealed that his snitch had put the “nose” on Joe McDonald and James Sims in New York.

“No way!” Connolly exclaimed.

Opie embellished the details, savoring Connolly’s unabashed jealousy at his score. He could see Connolly chomping at the bit over the whole story, suddenly second-guessing himself for outing his own informant. But alcohol drowned out his concerns, and Opie finished the evening on a high note. Connolly, meanwhile, soaked up every word instead of booze. He had other things on his mind.

The Organized Crime (OC) squad was supervised by a senior agent at the time who had about thirteen agents under him. Connolly charged into his office a few days later with John Morris in tow.

“This better be good,” the supervisor said, mincing no words.

“It’s better than good,” Connolly told him, after Morris had taken a seat. “We got people about to get dimed.”

Connolly proceeded to carve out the details of the secret New York operation Opie had shared with him, and the supervisor listened pensively through the whole tale.

“McDonald and Sims are supposed to give us key intelligence about Angiulo’s group in the North End,” he finally said. “Seems to me the mission of the Three Squad’s larger than a couple of muffs.”

“Yes,” Morris agreed.

Even though McDonald and Sims had been declared Top Ten fugitives, the OC squad’s mission was to get the probable cause needed for the wire to penetrate the Boston Italian mob. Arresting McDonald and Sims at this juncture would “queer” the whole priority objective for the squad. “Management by Objectives” had been the hallmark for the organized crime priority and all of them knew it.

“Fuck Opie,” the supervisor said. “His shit is penny-ante against ours.”

Although successful in gaining the supervisor’s support, Connolly and Morris blanched. They knew that Opie would now know they’d ratted him out and busted his operation to save their own. And they had an even bigger problem to contend with: Bulger and Flemmi.

Since harboring fugitives is a felony, and Bulger and Flemmi were hiding McDonald and Sims, they could lose their protected status as confidential informants. All it would take was for McDonald and Sims to fink them out to the New York office, leaving Connolly and Morris gnashing their teeth over the potential loss of their meal tickets.

But maybe there was a way they could come out of this okay and with the OC squad’s operation intact.

According to Colonel O’Donovan, Connolly went to Bulger and Flemmi and told them the news about Richie and the New York caper. As the news sank in, Bulger stared Connolly down, his dagger-sharp eyes loosening the agent’s bowels.

“So you want me to clean up your mess,” Bulger said.

“It’s your mess, too, now,” Connolly shot back, listening to his own voice as if it was somebody else’s.

For all Connolly knew, Bulger and Flemmi were going to whack him then and there. Instead, they simply turned their attention to the problem at hand.

Bulger called McDonald and Sims first. He told them they’d been ratted and needed to fly, and fast.

Next, Bulger summoned Richie himself and asked to see him about his boatrace. Richie boasted about the big bucks coming in, and Bulger responded by hitting him up for a loan for nearly all of the $800,000 take. Richie was happy to help his boss out. He was convinced the money would keep flowing his way, and that the loan only served to cement his relationship with Bulger.

After the meeting was done, Bulger was feeling especially good about how things had worked out. He had solved the problem Connolly had dumped in his lap and was now eight hundred grand richer for the effort. No doubt satisfied with a productive day’s work, Bulger had just one more call to make: to his most trusted assassin, John Martorano.