2026 congressional midterm elections

Seeking a flex-ible work schedule. Roy Rochlin/Getty Images

Jack Kennedy Schlossberg tried getting into the family business and lost, by like, a lot. Not as bad as George Conway but not great for the grandson of the beloved JFK. Since opponents criticized him for never having a real job, we thought we’d suggest some alternate career paths, if he’s done with politics. 

Reality TV Star

The producers of Love Island need to be knocking down his door right now. Or The Traitors, or Survivor, or Dancing with the Stars. I’m open to suggestions. He would make the perfect reality TV boyfriend and emotionally terrorize women on screen week after week. He would do great on the Island/Villa/Casa and he could put his influencer skills to good use. This is basically just like Congress anyways. 

Paddleboard Instructor

Since he loves to SUP in the Hudson, the Schloss can take the time to teach others his wicked swim skills. And it’s a good workout. From no PAC Jack to six pack Jack. 

Crypto Bro

Like any man that faces rejection (cough Eric Adams cough Andrew Cuomo) turning to crypto currency is the only logical way to process the loss. He can coin the “Kennedy Coin” and make a mint. And then lose it all. 

AI Spokesperson

Since he loves to use Claude for research and debate prep, Anthropic should rebrand Claude as “Jack” and then you can “Ask Jack” instead. That sounds so much better right? Though Anthropic’s incoming head of government relations Alex Bores might not like it.

Trophy Boyfriend

If he doesn’t have an Instagram model girlfriend now, he will soon. And since he can just accompany her around and live that  West Village Girl life, meeting friends for Aperol spritzes. He doesn’t even have to move from his place in Chelsea, it’s a state of mind. Plus there's a Fellini on 22nd Street.

Club Promoter for Billionaires

Mamdani’s policies like the pied-à-terre tax are really making the ultra-wealthy feel isolated these days. It can get really lonely in a 7,000 square foot Park Avenue penthouse. Jack can start a social club where people like this can find a safe space to be themselves. Maybe Dan Goldman can join.