With wiretaps all around him and investigators breathing down his neck, Gambino captain Angelo Ruggiero had enough problems in the spring of 1984. But when he called his attorney, Jon Pollok, one of the heavy hitters in the defense bar who took on the defense of Mafia figures, it was to ask a favor for someone else.

A friend of his, Ruggiero explained to Pollok, had a situation in which he needed some advice. Ruggiero brought around to Pollok’s Manhattan office on Madison Avenue a copy of the March 25, 1982, indictment involving Joseph Massino, the one that accused Massino, Benjamin Ruggiero, and the others of racketeering and involvement in the murder of the three captains. What did Pollok think of the case?

Pollok had never met Massino or even heard of him until that point. But looking at the indictment, Pollok saw something in it that made him think it was poorly drafted and possibly beatable in court. There didn’t appear to be a single substantive act of racketeering attributable to Massino that had occurred within five years of the indictment, the attorney remembered some years later. In plain English, for Massino to be convicted of being part of the racketeering enterprise known as the Bonanno crime family, he had to be convicted of two acts of racketeering within the five years preceding the grand jury issuing the indictment. Pollok didn’t see enough to make that case against Massino and said as much to Ruggiero.

“Would you like to take a ride?” Ruggiero asked his lawyer.

Pollok, a cautious man, had some trepidation about the cloak-and-dagger stuff, and his first reaction to the request was something like, “What are you crazy?” But his client insisted.

A few days later, Pollok recalled, he was driven by a man whose name he doesn’t recall over the George Washington Bridge into New Jersey, where he was blindfolded. Pollok was a New Jersey resident, and even though he was blindfolded he knew from the direction of the car’s continuing travel and the feel of the road that he was going west along Interstate 80. The only thing to the west along the road was the Delaware Water Gap and Pennsylvania. Soon, the car made a right turn and a half-hour later the car arrived where Pollok knew they had been going all along: rural Pennsylvania.

The car drove into a vacation bungalow area. Though it was late spring, there weren’t a lot of people in the area. Inside one of the buildings was Massino, “a fat guy,” as Pollok recalled. Massino said he wanted to know from Pollok what he thought about the case and whether he could mount a defense. Pollok shared with Massino the earlier assessment he had made. But being an officer of the court Pollok knew he had to convince Massino to return to New York and not remain a fugitive. Pollok had done a good sales job on Massino because a short time later, a matter of a few days it seemed, the fugitive gangster communicated to Pollok that he wanted to come back and for the attorney to see about bail.

Back in New York, Pollok and his partner, Jeffrey Hoffman, got to work on Massino’s surrender. Their first call, Pollok remembered, was to Assistant U.S. Attorney Louis Freeh.

“I want to bring in Joe Massino, let’s talk bail,” Pollok told Freeh.

The prosecutor, who would later go on to head the FBI, was tough and couldn’t be talked into agreeing to give Massino bail. Bring him back and then we can talk about bail was Freeh’s position.

“Can I see the boss?” Pollok recalled saying, referring to Barbara Jones, who had tried the 1982 case against Ruggiero and the others with Freeh.

As professional adversaries, Pollok and Jones had known each other for years and had come to appreciate each other’s abilities. Now head of the criminal section of the Manhattan U.S. Attorney’s Office, Jones had a great deal of power. Though it took some negotiation, Pollok said that he worked out what he thought was a “reasonable” bail package for Massino of $350,000 bond cosigned by his wife, Josephine, and secured by their marital home and two apartments Massino owned. The missing gangster was coming home.

News of Massino’s imminent return leaked out to his cronies, but oddly enough not to the FBI. In fact, special Agent Patrick Marshall and his colleagues continued to prowl New York City in search of the elusive Joseph Massino. It was a job that was getting old fast since the agents were hitting nothing but dry holes. Finally, in late June Marshall visited Gabriel Infanti, who was still smarting over the botched disposal of Bonventre’s body, and had the usual chat about needing to find Massino.

“Don’t worry, I hear he is coming back,” Infanti told Marshall.

Finally, on the morning of July 7, 1984, Salvatore Vitale drove Massino to Pollok’s office on Madison Avenue. From there, Massino, Jeffrey Hoffman, and Jon Pollok took a cab to Manhattan’s U.S. District Courthouse on Foley Square and walked up the long granite staircase to surrender. The time was 9:00 A.M., and in the company of the lawyers, Massino looked like anybody with business to do inside. Unlike Joseph Bonanno’s surrender some twenty years earlier after he had been on the lam, Massino’s return would not be taking anyone in the U.S. Attorney’s Office by surprise. At around 9:40 that morning, Assistant U.S. Attorney Barbara Jones got a call from the courthouse to notify her that her quarry had arrived.

“Miss Jones, what is the history here?” asked Magistrate Sharon E. Grubin after Massino’s case was called in the courtroom.

If she took the question literally, Jones could have spent hours relating the history of the Bonanno crime family and the role Massino was believed to have played. But she kept it short and sweet, telling Grubin that Massino had been indicted in March 1982.

“He was never arrested and subsequent fugitive investigation failed to locate him,” Jones said. “Within the last two weeks Mister Hoffman and Mister Pollok, lawyers for Mister Messina, contacted the government and advised us that he did wish to appear before the court and surrender to stand charges.”

By waiting, Massino had put himself in a better position for trial and he knew that. Had he stood trial with the other defendants in 1982, he risked being pulled into a vortex created by the presence of the others. Sometimes just sitting around the same table with your codefendants may create a poor inference about you in the minds of jurors. Massino was accused of involvement in the conspiracy to murder the three captains. Tape recordings introduced at trial contained the voices of Benjamin Ruggiero and Dominick Napolitano talking in conspiratorial tones and in substance to an undercover FBI agent about the killings. Massino’s name was mentioned in the recordings, but he himself was not overheard saying anything incriminating. Since no mobster had testified about the killings, the case was a circumstantial one at best and more so for Massino, who kept his distance from Joseph Pistone’s body recorder.

There was also the potential flaw in the indictment that Pollok had picked up on. Racketeering law had been steadily evolving since the famous 1970 RICO statute, formally known as the Racketeer-Influenced and Corruption Organizations Act. Prosecutors had been using it with some success against the mob, but it still presented problems on occasion and it wasn’t unheard of for indictments to be thrown out or convictions reversed on appeal.

But such problems wouldn’t come to light for many months. As Jones explained, part of the negotiations with the lawyers involved a bail recommendation that prosecutors had become comfortable with. The government agreed that Massino would be released on a $350,000 bond secured by the three properties. Appraisals had shown the amount of equity was enough to secure the bail package.

But a puzzled Grubin, considering Massino’s very recent history of being in the wind, said to Hoffman, “It is somewhat unusual to release a defendant on [a personal recognizance bond] who has been a fugitive for two years.”

Hoffman explained that the Massino family was putting its home on the line, a place where the defendant, his wife, and children had lived for over ten years. No matter what the charges, there were also some fine points about Massino’s record to consider.

One point was that the forty-two-year-old Massino had no prior convictions of any kind. Another factor was that while Massino was charged with a racketeering conspiracy involving three murders, he was not charged with actually committing the homicides, said the attorney. The only actual substantive crimes charged against Massino in the indictment centered on two hijacking allegations. In one count, Massino was accused of stealing a load of tuna fish, the other involved “dry goods,” said Hoffman, referring to the 1975 Hemingway truck hijacking. That had been the case that Massino was able to beat in court after his statements to the FBI were thrown out by a federal judge.

The recitation of the case history by Jones and Hoffman seemed to convince Grubin that Massino could have bail. But she had a duty as a federal magistrate to lay it on the line and tell Massino and his wife what would happen if he ever skipped town again.

“Is his wife in the courtroom,” asked Grubin. “Have her step forward, please.”

Josephine Massino approached Grubin and answered “I understand” when the magistrate told her that if her spouse didn’t show up in court each and every time he was supposed to that she would owe the government $350,000 and in the process possibly lose her house.

“Do you believe that he will show up in court when he is supposed to?” asked Grubin.

“Yes, I do,” Josephine Massino answered.

“And will you help him to do that?”

“Yes, I will.”

As the paperwork was prepared to secure the bond, Grubin next turned to Massino and told him that if he failed to show up when needed in court he could be prosecuted for bail jumping. That was a separate offense that carried a five-year prison term.

“Do you understand that?” Grubin asked.

“Yes, your honor,” answered Massino.

After entering a not guilty plea, Massino, Josephine, and the lawyers waited around lower Manhattan for a session later in the day with Judge Robert W. Sweet. It was Sweet who had handled the trial of Massino’s codefendants in 1982 and had sentenced them to prison terms ranging from fifteen years in the case of Ruggiero and Nicholas Santora to four years to a minor low-level defendant who pled guilty to a robbery conspiracy. A soft-spoken jurist, Sweet was quite familiar with the facts in the case after sitting through the earlier trial. Now, he faced a reprise of the case that would develop some very unexpected turns.