According to Jack Kennedy Schlossberg, as his name will appear on the ballot in Tuesday’s Democratic primary: Somehow, pretty much everything.
How brutal New York City machine politics really works. How the press can rip you apart. How far family connections can get you and how far they can’t. How hard it can be to keep a big smile and trademark double thumbs-up in photos while trying to keep loss and pain private. How utterly delicious so many have found his stumbles.
“Our party is just not good at selling our message – and that’s not everything, but it’s a huge part of it. And everyone says that it’s time for a new generation … the Democratic Party has got to learn how to do things differently – until somebody actually tries, and then they don’t want to,” Schlossberg told CNN, sitting at the revived H&H Bagels on Columbus Avenue, trying to stay upbeat.
The core idea of Schlossberg’s campaign to represent much of Manhattan in Congress: In an attention economy, a guy who very quickly turned his lineage into a massive online following and became a star of the last Democratic National Convention could connect with voters who think politics is pointless and their leaders are terrible.
But if multiple polls and the wariness of friends who have been helping him are proven right, Schlossberg is facing not just potential rejection but the prospect of letting down the Kennedy name and all the people who still get excited about it.
He could still emerge from an eight-candidate race for the 12th District that only requires a plurality to win. But rather than readying for the dawn of a new Camelot dauphin, Schlossberg is spending the final days of his campaign talking about the bot armies he believes have been created to astroturf bad comments about him online and having his allies put up “SELLOUTS BEWARE ↑” signs around the posters of his opponents.
CNN spoke to Schlossberg and several of his friends and donors, along with opponents who snipe that he’s barely been campaigning; that, according to people familiar with the matter, he didn’t realize when he started running that New York City’s ranked-choice voting system didn’t apply to the congressional race; that he has flipped out – both on X and in person – at rival consultants and others he’s determined are bad and insincere.
Between chatting with voters on a street corner on the Upper West Side last week, retiring Rep. Jerry Nadler interrupted an answer to another question from CNN to describe Schlossberg as “somebody with no credentials and no anything getting into the race.”
Nadler noted he had not gotten a heads-up from former House Speaker Nancy Pelosi, a longtime Kennedy family friend, when she endorsed Schlossberg to run for his seat.
Friends bemoan that this could have gone differently if someone had figured out how to manage Schlossberg’s charisma and talent, though they acknowledge he’s often made himself unmanageable. To arrange an interview with him, for example, the request goes to his personal assistant because he fired more traditional staff like a press secretary after the first few weeks of his campaign.