The scion of the Kennedy family has a skeleton. It lurks in the corner of the livingroom of his Chelsea apartment, wearing a silk grey and burgundy robe and a brown fedora that belonged to his grandfather.

President John F Kennedy was famous for going hatless, to the dismay of the hat industry.

“That’s why, you can tell, it looks completely new,” an amused Jack Schlossberg said.

Sitting in front of the skeleton are a few young people with laptops who are busy plotting Schlossberg’s run for Congress. There’s a whiteboard with “Congressman Jack” scrawled across the top, just above a vintage “Our Man Jack” sign from his grandfather’s 1960 presidential campaign.

The prize Schlossberg seeks is no less than New York’s glittering 12th district – encompassing the United Nations, the Empire State Building, Times Square, Central Park and this modest one-bedroom I’m standing in.

There are framed prints on the wall near a small grey sofa – Audrey Hepburn, William Shakespeare and Kings of Leon, his favourite band. Schlossberg likes to joke that he resembles Hepburn, and he told me that he has loved Henry IV, Part 1 since high school. He recited his favourite passage: “I’ll so offend to make offence a skill; redeeming time when men least think I will.”

It is fitting that Schlossberg (32), loves Prince Hal, who played around until he rejected Falstaff and tankards and decided to act more responsibly and pick up the mantle of his royal family.

Schlossberg has no Falstaff; he says he doesn’t even drink or use drugs. But, like Prince Hal, he has been searching – dabbling in different jobs and personae.

In a sharp departure from the expected path for a Kennedy interested in politics, Schlossberg entered public life by carving out a role for himself as a charismatic – and sometimes pugnacious, crude and off-the-wall – social media personality, amassing just over 1.7 million followers across X, Instagram and TikTok. Many young people were excited to have another eligible Camelot heart-throb with a thick head of dark hair, this one madly oversharing.

If Schlossberg has been offending to make offence a skill, like Prince Hal, he is also redolent of Hamlet, who feigns being crazy to carry out a serious mission (and ends up doing some crazy things).

On social media, Schlossberg sparred, trolled and went on the attack, often feuding with family members.