In the annals of American crime history, few figures are as perplexing and chilling as Harold Konigsberg. His story, a twisted tapestry of confessions, manipulations, and courtroom theatrics, began to unravel in the spring of 1965 within the stark walls of Danbury Federal Penitentiary in Connecticut. It was there that a team of FBI agents first encountered the enigmatic Harold, a man who held them captive with fragmented narratives and a penchant for his own voice. Agent John Connors, who had been on Harold’s trail since the early 1960s, recounts, “He would give you part of a story, because he said you already knew the rest. He goaded you into asking questions he wasn’t going to answer. But he got carried away. He liked listening to himself talk.”
Initially, Harold painted a picture of the Mafia’s intricate hierarchy, detailing the power dynamics within families, the ownership of various rackets, and the preferred haunts of gangsters indulging in their daily marinara. However, by May 25th, mere intelligence gathering had lost its allure for Harold. “This is nothing,” he declared to the agents, dismissing the mundane details. “Why be interested in nickels and dimes?” With this pronouncement, Harold transitioned from informant to confessor, embarking on a chilling catalog of his own Mob hits.
To validate his gruesome claims, Harold directed the FBI to a clandestine Mob graveyard in Jackson Township, New Jersey. There, agents unearthed the skeletal remains of two individuals believed to be victims of Harold’s deadly craft. One, suspected of being an informant, was entombed beneath a concrete porch. The other, a theatrical agent burdened by debt, was discovered stuffed inside a metal drum in a chicken shed, allegedly doused with acid as per Harold’s account. Adding another layer of macabre evidence, investigators also recovered hair and bone fragments, possibly belonging to a woman whose husband was entangled in the production of pornographic films.
The FBI’s meticulous record of Harold’s confessions listed a staggering twenty murders, deaths, and disappearances, painting a grim portrait of his life in the shadows. Yet, amidst this litany of violence, the government harbored a primary objective: to connect Anthony Castellito’s murder to Tony Pro, a Mob figure of significantly greater consequence than Harold himself. Robert Kennedy, in his exposé “The Enemy Within,” described the Teamsters union as a “conspiracy of evil” and “the most powerful institution in this country—aside from the United States Government itself.” Against this backdrop, the pursuit of Tony Pro intensified, especially considering the recent murder of another union challenger and the indictment of Jimmy Hoffa and seven others for a massive fraud involving the Central States Pension Fund.
Harold willingly recounted the details of Castellito’s murder to the FBI. However, his cooperation came with a price. He demanded immunity from prosecution in pending extortion cases in Philadelphia and New York in exchange for his testimony. William Hundley, head of the organized-crime unit at the Justice Department, found this proposition palatable. He even suggested extending immunity to Harold for all crimes he confessed to, provided he assisted in locating Castellito’s body. Regarding the New York prosecution, Hundley confidently assured his superiors in a memo of his ability to handle it “informally.” To the dismay of the Manhattan D.A., the Feds strategically placed Harold in the Medical Center for Prisoners in Springfield, Missouri, effectively prolonging his charade under the guise of psychiatric evaluations for another year. Simultaneously, the case against him in Philadelphia quietly disappeared.
When the stage was set, Harold was discreetly transported by train to Newark and then to Somerset County jail. His identity remained concealed even from the warden. On June 30, 1966, under the watchful eyes of marshals, he led authorities to farmland east of Freehold Township, purported to be Castellito’s burial site. “We looked for two days,” recalls Arnold M. Stone, the Justice Department lawyer spearheading the search. “We didn’t find Castellito. Harold kept saying, ‘It’s gonna take a while.’” Harold revealed that he had received a letter from his wife indicating that the body had been moved. Hopes for discovering traces of the corpse or evidence of disinterment through laboratory tests were dashed. Despite recognizing the terrain, Harold failed to pinpoint the exact burial location.
The absence of a body undermined the Feds’ ability to shield Harold from the legal system. In December 1966, he was returned to lower Manhattan to face trial in one of the extortion cases. In a calculated move, Harold attempted to provoke a mistrial by accusing his lawyer, Frances Kahn, of being a “spy” for the D.A. and promptly firing her. Yet, in a bizarre twist, he retained Kahn and Frank Lopez as “paralegal assistants” for his pro se defense, relying on them to feed him notes from the defense table. Harold later recounted, “I had my wife sit alongside of me and look up words in a dictionary.”
Leonard Newman, one of the prosecutors, remembers the spectacle Harold created: “People lined up outside 100 Centre Street to see the show he put on.” Harold’s courtroom attire was consistently mismatched, complemented by what the Times described as a “King of Clubs beard.” He relentlessly bullied witnesses and, when Judge Abraham Gellinoff overruled him, accused the judge of concealing exculpatory evidence.
Frank Rogers, an ambitious assistant D.A. eager to make his mark, represented the prosecution in his first major case. A law review alumnus from St. John’s, Rogers was described as a skinny man beginning to show signs of middle-age weight gain, always impeccably dressed in three-piece suits and rarely seen without his pipe. Harold immediately targeted Rogers, unleashing a torrent of insults, labeling him a “bigot, sadist, low-life, reptilest, fork-tongue talker.” He even called Rogers to the witness stand on four separate occasions, prompting Rogers to lament, “Every time he runs out of witnesses, he calls me.”
In a particularly theatrical cross-examination of a psychiatrist brought in to assess his sanity, Harold spent an hour constructing a hypothetical scenario before finally posing his question: “Now, Doctor, assuming everything I’ve said to be true, do you have an opinion as to whether District Attorney Rogers is crazy?”
Despite the gravity of the situation, some observers initially held a flicker of sympathy for Harold. Murray Kempton, writing for the Post, captured this sentiment in a sorrowful dispatch: “One went . . . preparing to salute one of the giants of the American struggle for Constitutional liberty. . . . One fled after the second hour with an idol crumbling in the dust behind.”
As the trial progressed and Harold’s pronouncements became increasingly erratic, Judge Gellinoff intervened. “Mr. Konigsberg, listen, my friend, now I’m—”
“‘My friend’? You got ten dollars, I’ll sell you back your friendship,” Harold retorted, showcasing his characteristic cynicism.
The following day, Judge Gellinoff’s composure finally shattered. After excusing the jury, he erupted, “Shut up when I’m talking. You are the greatest faker in the history of the court that I know of. . . . You are one of the most brilliant people that I have ever seen as a defendant in this court. . . . I have said these things on the record so that you will know, Mr. Konigsberg—”
“That you’re prejudiced?” Harold interjected.
“—you will not get away with this,” Gellinoff concluded, his frustration palpable.
The jury ultimately found Harold guilty on four counts of extortion and one of conspiracy, but remained deadlocked on four other counts and acquitted him on one. On sentencing day, Harold refused to acknowledge his identity as the Harold Konigsberg convicted of two prior felonies. This defiance compelled Judge Gellinoff to empanel a new jury solely to establish Harold’s identity, adding another five weeks to the legal proceedings. Gellinoff eventually handed down a harsh sentence of thirty to forty-four years, remarking with a hint of irony, “You’re developing into quite a constitutional lawyer.”
Even with this conviction, Harold had effectively evaded justice for murder. Peter Richards, a Justice Department prosecutor, pleaded with his superiors in a memo dated October 31, 1967: “It seems to me impossible to allow this man, who has confessed to more than twenty murders and who has told us that he will ‘go gunning’ for his enemies when he is released from prison, ever to be released from custody.” Fearing a reversal of Gellinoff’s sentence, the Feds attempted to leverage Harold’s confession to the Castellito murder against him, even preparing an indictment. However, they soon abandoned this effort. Without a body or an eyewitness, the evidence was insufficient to prosecute him for murder. The FBI’s extensive interviews with Harold had yielded little more than embarrassment and frustration.
Harold’s motivations for confessing were not rooted in remorse or a desire for justice. He spoke to the FBI for sheer amusement, reveling in his ability to manipulate authority figures and subject them to his elaborate games. “Now, there’s a lot of things I’m guilty of,” he once confessed, almost tauntingly. “I’m just saying, catch me on something.”
Paul Durkin, the primary FBI agent assigned to Harold throughout this tumultuous period, when contacted, stated, “I don’t want to get into discussing our relationship.” When pressed for the reason, he simply replied, “It’s because I liked him.” This unexpected sentiment underscores the complex and unsettling nature of Harold’s personality.
Not long after the extortion trial, D.A. Rogers and Detective Joseph Coffey brought Harold in for questioning, unaware of the extent of his previous confessions to the FBI. “We wanted information on other people, so Rogers made the mortal fuckup of giving him immunity,” Coffey recounted.
Frank Lopez, who was also present during the interrogation, added, “They had no idea Harold was going to implicate himself.”
At the time, Coffey was investigating the unsolved homicide of Johnny Earle, a waterfront racketeer gunned down nine years prior in front of a lunchtime crowd at the Fifty-seventh Street Cafeteria, near Eighth Avenue. “It was the first thing every cop asked,” Coffey explained. “I said, ‘Who killed Johnny Earle?’ ”
“Yeah, I did that,” Harold casually responded. He proceeded to provide intricate details, even directing them to corroborating evidence – a parking ticket he had received while inside the diner. Coffey stated that Harold then confessed to five additional killings. “But he didn’t give us a thing we could use. Rogers was devastated.” According to records from another detective present, the tape recording of Harold’s confession mysteriously disappeared. Coffey confirmed that the Earle case was closed as solved without an arrest, concluding, “He was an unusual guy, your uncle. He didn’t care about doing the forty-four years as long as he got over. In his own mind, he showed he was smarter than everybody else. Because he made a wreck out of a top judge like Gellinoff. And he sucked Rogers in, like unbelievable.”
Big Sal Sinno, Harold’s accomplice in the Castellito murder who vanished shortly after the crime in 1961, was not entirely forgotten. Later that year, fearing Tony Pro’s wrath, he fled to Milwaukee, adopting aliases and working for the railroad. However, his life took a downward spiral, and his girlfriend, the mother of his two sons, resorted to prostitution. Big Sal later described the ensuing family turmoil as “hard on the family” and recounted numerous fights.
In 1975, seeking revenge after Big Sal physically assaulted her, his girlfriend made a long-distance call to the Hoboken police. She informed them that a “Charles Caputo” residing in Fond du Lac, Wisconsin, was in fact Big Sal Sinno, “wanted in Hoboken, N.J., for some serious crime,” as puzzled officers recorded. Upon discovering the phone bill and realizing his girlfriend’s betrayal, Big Sal hastily fled with his children, attempting to reconcile with Tony Pro and requesting funds to relocate once more. He received twenty-five hundred dollars and a promise of another twenty-five hundred upon in-person collection, a proposition he suspected was a setup.
It was then that Big Sal contacted the FBI, desperately seeking entry into the witness protection program. Special Agent John Markey inquired about what Big Sal could offer in return. Big Sal offered the Castellito story, reopening a cold case and setting the stage for a dramatic legal showdown.
In the summer of 1978, Kayo Konigsberg, Harold’s brother, was finally brought to trial for the Castellito murder, alongside Tony Pro. (The other implicated individuals were by then deceased or missing.) For procedural reasons, Michael Kavanagh, the District Attorney of Ulster County, New York, where the crime had occurred, led the prosecution. “We were in over our heads,” Kavanagh, then thirty-four and new to the job, recalled. “It was one of your bigger Mafia trials to date, in Kingston, our little Colonial county seat of twenty thousand. You’ve got guys right out of ‘The Godfather’ pulling up in limousines. You’ve got sharpshooters on top of the jewelry store across the street.”
Harold’s lawyer, Ivan Fisher, took on the case for a mere twenty-five hundred dollars in expenses. Yet, Harold, even from behind bars, proved instrumental in their defense. Fisher recounted, “During our lunch breaks, he ordered in four-pound buckets of shrimp, with fresh tartar sauce and Russian dressing.” Amidst this unusual legal feast, Harold utilized the phones to unearth crucial information. He discovered that the New York Secretary of State held a file on a real-estate agent in Kerhonkson, who was slated to testify about seeing Harold on Castellito’s property on the day of the murder. Crucially, the state had suspended the real-estate agent’s license for writing bad checks – a detail that could severely damage the witness’s credibility. Although Fisher attempted to leverage this information during cross-examination, the D.A.’s objection was sustained. Despite this setback, a guilty verdict was delivered for both defendants. However, Harold appealed, successfully overturning his conviction and forcing a retrial.
“The judge’s preclusion to that cross ultimately caused the reversal,” Fisher explained. “Our case was built on Harold’s investigation. I have no idea how he got the file. The prosecution didn’t even have a copy.” This final twist in the saga of Harold Konigsberg underscored his uncanny ability to manipulate the legal system, even while incarcerated, leaving a lasting and unsettling mark on the landscape of Jersey City’s criminal underworld and beyond.
