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Politics & Media
Jun 03, 2026, 06:29AM

Jack’s on the Right Track

Schlossberg’s Congressional candidacy is perfect for 2026.

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It’s unlikely that John Bouvier Kennedy Schlossberg (Jack), the playful Millennials-just-wanna-have-fun grandson of JFK, is familiar with the 1959 Coasters’ smash hit, “Charlie Brown,” with its memorable line, “Why’s everybody always picking on me,” but if a musicologist on his payroll is smart, it’d make a great ad for his quest to represent New York’s 12th Congressional District. (It’s a safe Democratic seat, and despite the outrage from journalists and party insiders that Jack’s making a mockery of the campaign, that’s hard to reconcile since Jerry Nadler has embarrassed that district since 1992.)

As I wrote last November, there’s no downside to a Jack win: he’s 33, has an active and bizarre (a plus, unless you’re Graham Platner) social media presence, and like Donald Trump is willing to say anything outrageous to get attention, and maybe make quiet retractions later. (I don’t like Jack’s politics—such as they are— but the same’s true for his competitors.) There are exceptions, but both chambers of Congress are more boring than Bob Dole’s 1996  presidential campaign against Bill Clinton. In an era where politics is the country’s leading entertainment (at least right now), there are few politicians who are helping Trump (the nation’s top comedian) do the heavy lifting, although inadvertently AOC, Lindsey Graham, James Talarico and Chris Van Hollen are in the mix.

Jack, almost assuredly, would vote a straight Democratic line if elected to Congress, so I’m missing the severity, and nastiness, of the complaints.

The New York Times’ Michelle Cottle, in a May 28th column (“He’s Entitled and Nepotistic. This is Not What Democrats Need.”), influenced by Mr. Peabody, with Bullwinkle, Boris, Sherman and Natasha looking on, writes with exasperation: “In some cases, the golden aura of the [Kennedy family’s] beloved brand seems to take the place of vetting individual members, saddling the public with uninspiring or even unfit leaders.” The “unfit” is applied most vehemently to Bobby Jr.’s admittedly weird place in the Trump orbit, but she touches on some other Kennedys as well.

Cottle (with the Times since 2018, is a Maryland resident, so her pique about Jack is odd, not to mention disagreeing with Lady Nancy Pelosi, who endorsed Caroline’s son. She isn’t a royalist! No kings! But she writes from another time zone: “So reminisce about the cultural cool of Camelot all you want… But for the love of God and the sake of our democracy, let us stop treating Mr. Schlossberg and his extended family as inherently worthy of important political jobs that affect the lives of real people.”

Is Cottle one of the “real people,” too? Probably not—the Times doesn’t employ mere “real people”—but I got a kick out of her implication that Jack’s election would endanger democracy. Democrats, except those who deviate from the norm, aren’t allowed to encroach on Trump’s turf. She adds: “Some children of fame and privilege grow up committed to working extra hard to prove themselves. Mr. Schlossberg does not seem to have chosen that path.” She doesn’t provide a single example of a privileged child who worked extra hard to shake the “sin” of nepotism; Cottle could’ve gone down on the Sulzberger clan that’s run the Times for 130 years, but probably wasn’t up for “brown-noser” ribbing she’d endure from colleagues.

In fact, the “beloved brand” of the Kennedys all but disappeared after Uncle Teddy’s cowardly lack of action at Chappaquiddick in 1969, and public womanizing and intoxication in subsequent years, before his “rehabilitation” earned him the ludicrous “Lion of the Senate” tag. Since then, no other Kennedy has advanced to the U.S. Senate (although a couple of the third-generation scions had relatively brief and inconsequential stints in the House). More importantly, how many voters across the country under the age of 65 have any memory of “the cultural cool of Camelot”? It’s not relevant, and, flipping the coin, neither is the wave of nostalgia among some conservatives for the aborted Nixon Administration.

Cottle does let down her guard near the end of her column: “Look, nostalgia is a heckuva drug. I, too, long for a simpler time when my phone wasn’t spying on me—or when Donald Trump was a mouthy playboy rather than a duly elected menace to democracy. And who doesn’t feel a pang looking at the iconic photo of 3-year-old John-John saluting his father’s coffin?” As an eight-year-old I watched JFK’s funeral, and the choreographed (as was revealed later) John-John salute was poignant. But that was 1963 and, like everything else in American culture today, politics is a far different form of civics/entertainment. Don’t blame Jack!

—Follow Russ Smith on Twitter: @MUGGER2023

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