Post reporter spends day in cushy life of Jack Schlossberg — politics’ newest (and work-shy) nepo baby

Call me a Jack of all trades.

Or perhaps no trades.

I was the envy of the office when my editor asked me to spend a day living like Jack Schlossberg, the occasionally employed political scion most famous for feuding with family members, celebrities and strangers on social media.

“Some reporters get dispatched to war,” one colleague tartly remarked. “You’ll get to kick back, relax and do nothing.”

Since graduating from Harvard Law School in 2022, there’s been the assumption that the 32-year-old Park Avenue-raised grandson of John F. Kennedy has been living life on easy street.

Unburdened by pesky student loans (Harvard Law tuition costs a cool $80,000 a year), Schlossberg has been free to spend his time paddleboarding, posting to TikTok, and working at a surf shop in Hawaii.

So, news this week that he’s making a run for Rep. Jerry Nadler’s soon-to-be vacated seat in New York’s 12th Congressional District has raised eyebrows, given his résumé is as slender as his 6-foot-2 frame.

But the self-described “silly goose” is a serious contender.

As Zohran Mamdani’s mayoral victory proved, experience counts less than charisma — and Schlossberg has it in spades.

His hundreds of thousands of social media followers fawn as he saunters around the city, singing, cycling, and imitating various public figures.

My editor asked if I was up for the challenge of living like Jack. After all, what’s more Jack Schlossberg than poking gentle fun at someone in the spotlight? As they say, imitation is the sincerest form of flattery.

To be clear, we don’t have much in common: He’s a little younger, his hair is a lot thicker — and there’s also the matter of his multi-million-dollar trust fund.

But there are some similarities: namely, our need for attention and the enjoyment we both clearly get from seeing our pictures in the paper.

Taking voters for a ride?

Schlossberg doesn’t shy away from his impressive lineage, even as Democrats rally against nepotism and “white privilege.”

The same people who attend “No Kings” rallies have cheekily crowned Schlossberg “the people’s princess.”

Like his forebears, the savvy scion is utilizing modern media to help craft his image — one that’s equal parts corny, cool and ironic — but some say he’s riffing a little too hard.

Campaign photos that show Schlossberg cycling through the city are an obvious ode to paparazzi pictures of his late uncle, John F. Kennedy, Jr.

It’s prompted critics to wonder whether Schlossberg is simply taking voters for a ride — literally and figuratively. Is this entire campaign just a vanity project? Something to keep the Camelot mythmaking machine alive?

Time will tell how it all pans out, but Schlossberg seamlessly weaves in and out of Manhattan traffic while carrying both flowers and a skateboard.

My attempt: a little less graceful.

He memes business

While many might dismiss Schlossberg’s incessant TikTok and Instagram use as a folly, he’s meeting millennial and Gen Z voters where they are.

To his credit, it’s hard to break through on social media — and the Harvard grad is a master meme-maker.

And if he’s not working a job, he’s certainly working his angles.

Schlossberg can perfectly pose for selfies and shirtless snaps, like the one below. (Disclaimer: I refused to take my shirt off for this assignment, and your eyes will thank me for that.)

Schlossberg boasts nearly a million followers on TikTok and Instagram each — and he needs the edge.

The race to represent the 12th Congressional District is already shaping up to be uber-competitive, and Schlossberg can’t rely on his good looks to get him over the line.

The primary is already set to be packed with young, dreamy Democrats.

Alex Bores, the 35-year-old Cornell-educated hunk who currently serves in the New York State Assembly, has already thrown his hat in the ring.

Yale grad and Rhodes Scholar Liam Elkind is also a contender, as is Cameron Kasky, a 24-year-old survivor of the Parkland school shooting.

Instagram account @thatgaygucandlecompany quipped: “Is New York’s 12th congressional district about to experience the hottest primary ever?”

Take time to smell the flowers

Schlossberg announced his Congressional bid in a 4,500-word New York Times piece that was heavy on the details of his social media spats, but curiously light on talk about politics and policy.

Is Schlossberg, who endorsed Zohran Mamdani, a Park Avenue populist? What does he think of the price of groceries? And what would he say to critics who accuse him of never having held down meaningful employment in the district he aims to represent?

It’s all unclear — but the piece did note that he loves to keep flowers in his “modest” one-bedroom apartment in Chelsea (rents for similar lodgings list for upwards of $5,000 a month on Zillow).

The Times piece was accompanied by pictures of the aspiring politician popping into a florist to pick up some flowers, so obviously I had to follow suit.

Schlossberg’s lack of policy proposals has already alarmed some, including the progressive political account Notice News.

The millionaire has mentioned a “cost of living crisis,” but it remains to be seen whether he can really connect with cash-strapped millennials and zoomers who are increasingly anxious about their financial futures.

Navigating choppy waters

Schlossberg is an avid stand-up paddleboarder, often seen traversing the Hudson River, so a real day in the life wouldn’t be complete if I didn’t follow suit.

Sadly, however, I wasn’t up to the task.

A recent night kayak on the Hudson had me terrified — and I arrived back on dry land in tears.

Jack is clearly braver than I — and running for public office is no small feat.

Who knows how he’ll fare, but when you’re Jack Schlossberg, the wind is always at your back.