Living Like Jack Schlossberg

Call me a jack of all trades. Or maybe, just no transaction.

When my editor suggested I immerse myself in the life of Jack Schlossberg, the sometimes-job-holding political figure known for his social media spats, I was met with a wave of office envy.

“Some reporters go to war,” one colleague remarked bitterly. “You get to kick back and do nothing.”

The 32-year-old grandson of John F. Kennedy, who grew up on Park Avenue, is often perceived as living a charmed life since graduating from Harvard Law School in 2022. He’s managed to avoid hefty student loans—after all, Harvard’s tuition is a staggering $80,000 yearly. Now, he spends his time paddleboarding, TikTok-ing, and working at a surf shop in Hawaii.

So, news of his candidacy for Congressman Jerry Nadler’s soon-to-be-empty seat in New York’s 12th Congressional District raised eyebrows. His resume is, well, a bit thin—much like his 6-foot-2 frame.

But calling him a “stupid goose,” he’s surprisingly a serious contender. Zoran Mamdani’s recent mayoral win underlines that experience often outweighs charisma, and Schlossberg has that in abundance.

With hundreds of thousands of followers online, people enjoy watching him roam around the city, singing, biking, and mimicking various celebs.

My editor wondered if I could embody Jack’s lifestyle. After all, what’s better than gently poking fun at the prominent figures? I suppose you could say imitation is flattery.

Truth be told, we don’t have much in common. He’s younger, with thicker hair, and then there’s that impressive trust fund of his. But I suppose we share a desire for attention and an apparent delight in seeing our faces in the news.

Will You Give Voters a Ride?

As Democrats contend with issues of nepotism and “white privilege,” Schlossberg embraces his lineage. At rallies, he’s been playfully referred to as “the people’s princess.”

Like his predecessors, he’s savvy with modern media, crafting a blend of irony and charm. However, there’s chatter that he may be overdoing it. A recent campaign photo of him biking through the city looks like a nod to the paparazzi snaps of his late uncle, John F. Kennedy Jr.

This raises eyebrows about whether Schlossberg’s campaign is a serious political endeavor or just a vanity project aimed at keeping the Camelot legend alive.

Only time will tell, but it’s clear he navigates Manhattan seamlessly, even while juggling flowers and a skateboard. My attempts to replicate that grace—let’s just say they fell short.

The Meme Game

When not busy working, it seems Schlossberg is perfecting his social media poses. Amazingly, he knows how to engage Millennials and Gen Z through TikTok and Instagram. Not an easy task, really.

He shines in the meme department, displaying a knack for capturing the moment perfectly. And no, I didn’t dare take my shirt off for this piece. Trust me, you’re better off.

With around a million followers on both platforms, he’s got his work cut out for him. The competition to represent New York’s 12th Congressional District is heating up, and looks alone won’t carry him through.

Current rivals include Alex Boaz, a 35-year-old Cornell grad, Yale graduate Liam Elkind, and Cameron Kasky, a 24-year-old Parkland survivor.

One Instagram account cheekily asked if the district was about to experience its “hottest primary ever.”

Take Time to Smell the Flowers

Schlossberg has announced his congressional bid through a lengthy New York Times article. Strangely, it focused more on his social media antics than on actual political stances.

Is he, in fact, a Park Avenue populist? What’s his take on rising food prices? And how will he address those who say he hasn’t done meaningful work in the district he seeks to represent?

All remain big questions. The article did mention his love for decorating his “modest” Chelsea apartment with flowers, despite the fact that similar rentals go for over $5,000 a month.

In a bid to mirror his actions, I decided to visit a local flower shop for a photo op of my own.

However, concerns over his lack of clear policy proposals are surfacing. He talks about a “cost of living crisis,” but can he truly connect with cash-strapped Millennials and Zoomers worried about their futures?

Sailing in Waters with Strong Waves

Schlossberg is a committed stand-up paddleboarder, often seen on the Hudson River. So, naturally, I felt compelled to try it out too.

Unfortunately, I fell far short of the mark—night kayaking left me shaken and back on solid ground in tears.

Let’s be honest, Jack has a bravery I can only admire, and running for office is a significant endeavor. What lies ahead for him? With Jack Schlossberg, the winds always seem to favor him.