James “Jimmy” Beaudoin II was born the first time in March 1991 in Fort Lauderdale, the eldest son of a hardscrabble single mother. Then, in his early 20s and hoping to escape the dead end of his past, he was reborn in New York City. In March 2015, not three years after landing in the city with little more than the shirt on his back, Jimmy Beaudoin legally changed his last name to Rackover. For the court petition, he obtained the consent of a wealthy older Manhattanite named Jeffrey Rackover, a diamond dealer dubbed “jeweler to the stars” who had become a surrogate father to him. While it wasn’t a formal adoption, it proved a symbolic one, the shedding of a former self in order to don the fineries that New York sometimes bestows upon its most ambitious and adaptable newcomers. The two men didn’t look much alike—Jimmy is muscular and tall with the square, wide face of a brooding 1950s matinee idol; Jeffrey is none of those things. Nevertheless, for the sake of convenience and to ward off any implications of a sexual relationship, Jimmy was introduced around town as Jeffrey’s long-lost biological son. Much was given to Jimmy Rackover, and much was expected in return. He wore tailored Savile Row suits, had his shirts made by Anto in Beverly Hills, and spent his summers poolside in East Hampton. He took the subway “like two or three times when I first got to New York, and that’s it,” preferring Ubers and taxis. He used his Equinox gym membership twice a day, brought women on first dates to the Upper East Side Italian mainstay Campagnola, and hit nightspots like Tao, the PHD lounge, and Happy Ending. He had a full-time job as an insurance broker specializing in jewelry and fine art at Willis Towers Watson. By any estimation, his was a rapid ascent into the tight, often impermeable social weft of the city. “I always felt like I was meant to be something bigger,” Jimmy tells me about his desire to make it in New York.

“There are all these stories about him and I, and all this gay-lover shit. All I did was go out and chase girls.”

For a long time, the princely reinvention seemed complete. Then came a Saturday night in November 2016, when Jimmy hosted a small after-hours party in his posh Sutton Place apartment that ended in a vicious murder. A little after dawn on that Sunday morning, as the other guests made their way home, four men remained inside the apartment: Jimmy, his best friend Larry Dilione, Larry’s childhood friend and roommate Max Gemma, and an affable Connecticut native named Joey Comunale, who had been a stranger to the others until that night. One or more of these men is a murderer. Inside the apartment, Joey was violently beaten and stabbed 15 times in the chest—nine on the right side and six on the left. The questions why, how, and by whom still linger. The murder itself was largely overshadowed by the brutality of the cover-up. After an attempted dismemberment in the bathtub using a kitchen knife, Joey’s body was wrapped in plastic and a bed comforter, tossed from Jimmy’s fourth-floor window onto a busy Manhattan sidewalk, packed into the trunk of a Mercedes Benz, and driven to a secluded spot in Oceanport, New Jersey, where he was set on fire and buried in a shallow grave. It would take three days before police found the body.

“I didn’t see any of this coming,” Jimmy tells me, sitting in a tiny cinder block room in the visiting area at Attica. Since April 2019, he has been incarcerated in the maximum-security prison in the northwest corner of New York State, serving a sentence of 28 years to life for murder in the second degree. “I thought I’d just be coming back from the Hamptons right now, like a regular cycle of my life.”

There are no guards or listening devices in the room, yet Jimmy is reluctant to talk. Since his arrest on November 15, 2016, he has not once been out of police custody, and in that time he has never spoken to investigators. He didn’t take the stand at his trial and he didn’t speak at his sentencing. From the very start, he was cast as the poster boy ringleader of a sadistic, partying-too-hard murder. Footage of him being led out of Manhattan’s 13th Precinct wearing a midnight-blue Prada suit over a white V-neck T-shirt, his wrists in handcuffs, became instant tabloid fodder. Yet he has remained overwhelmingly silent. Silence can save you, especially in the criminal-justice system, but it also allows you to fit neatly into anyone’s preferred version of events.