Thomas Gilbert, Jr.

BA, Princeton University

^*

Tommy Gilbert was well born and well built. He not only looked like a particularly handsome surfer boy, he was an actual surfer—in the Hamptons! So perhaps it was a combination of his looks, his parents’ money, and his social connections that kept many of the people who knew him from reacting when he started losing his shit.

“I’m a graduate of Buckley,” he wrote, in late 2015, in a letter to Manhattan DA Cyrus Vance, Jr. Buckley, which Gilbert and Vance^* had both attended,^* is a prep school on the Upper East Side; Gilbert also name-checked two more high-tuition alma maters, Deerfield Academy and Princeton. He sent the letter from the Manhattan Detention Complex—a.k.a. the Tombs—many blocks south of the Upper East Side. “Fortunately,” he went on, “I’ve had access to the newspapers and have enjoyed reading articles about the DA’s offices and the city’s various cases. I was impressed by the overall decline in crime this summer.” After the ass-licking, he gets down to business, complaining that he’s not the sort of person who flourishes in jail, that he’d been “railroaded,” and that he ought to be released to protect and preserve his “personal life” and his “career.”

His career consisted mainly of sponging off his parents—he was thirty-one—while pretending to acquaintances that he was starting a hedge fund. As for his personal life, there were three outstanding episodes for which he was known.

• In October 2013 Gilbert had, for no reason, beaten the living shit out of Peter Smith, his Brooklyn roommate and fellow Buckley alum.

• Prior acts of violence and other circumstantial evidence led police to question Gilbert about the fire that, in September 2014, destroyed Peter Smith’s family’s lovely historic house in the Hamptons. As of this writing, Gilbert has not been charged and the case remains unresolved.

• On January 4, 2015, visiting his parents’ Upper East Side apartment, he asked his mother to run out and fetch him a sandwich. That she complied and didn’t say, “Either make one yourself or go out and fetch your own fucking sandwich” is, in and of itself, enough to make one think, “Jesus. These people.” Then it got worse. Tommy Gilbert shot his father* point-blank in the head, placed the pistol on his dad’s chest to make it look like a suicide, and left in a hurry.

He was arrested a short time later—hence his stay in the Tombs—in his own apartment in Chelsea.

He was said to be furious with his father for threatening to cut his $600 monthly allowance down to $400.^*