Quitting Biden, Proving A Point
He explains leaving the campaign altogether.
Design Matters with Debbie Millman
Mar 9, 2026 · 42 min · 31 segments
Jack Schlossberg—the writer, lawyer, political correspondent, and only grandson of President John F. Kennedy—joins Debbie Millman live at On Air Fest to discuss political legacy, internet culture, and…
In the meantime, um, you went to Yale University, where you wrote for The Yale Daily News, you were editor of The Yale, Yale Herald, and in an article titled, "In Rally Behind the President," you argued that Democrats do not always play the game of politics correctly.
Uh, I believe in it because I know the history, and to me a Democrat is somebody who has been fighting for decades for civil rights, for working people, for labor, for immigration reform, for sensible economic policy, that has a party that has a job record that beats the Republicans 50 to one.
So I feel like that story and that history and that association is not something that a lot of people my age or younger really have with the Democratic Party, and I think it's hard when you, uh, are competing against another side that, in my opinion, plays by different rules, uh, doesn't feel obligated to tell the truth or explain or be correct on policy.
And I think, obviously, I don't want us to get the answer wrong, and a, the only reason to be in politics is to try to make a smart policy.
And I don't know how Democrats became associated with being stale, being stuck in the past, risk averse.
So I think in a lot of ways Democrats hamstring themselves by trying to get the answer right, trying to, uh, explain the problem, and don't remember to be funny, take risks, tell stories, and I think that that's why I'm running for Congress.
I don't think we need to forfeit social media following to the other side.
And I think that there's absolutely no reason that we can't be cool, fun, edgy, and break through, because at the end of the day, I think our policies are way more popular with the American people than the other side.
I mean, he is still one of the coolest dudes in the universe, so how that happened is something that I think people are trying to understand, and in many ways it's a branding and positioning exercise, because how did we lose that so quickly? I mean, we're talking about a decade.
In the meantime, um, you went to Yale University, where you wrote for The Yale Daily News, you were editor of The Yale, Yale Herald, and in an article titled, "In Rally Behind the President," you argued that Democrats do not always play the game of politics correctly.
Uh, I believe in it because I know the history, and to me a Democrat is somebody who has been fighting for decades for civil rights, for working people, for labor, for immigration reform, for sensible economic policy, that has a party that has a job record that beats the Republicans 50 to one.
So I feel like that story and that history and that association is not something that a lot of people my age or younger really have with the Democratic Party, and I think it's hard when you, uh, are competing against another side that, in my opinion, plays by different rules, uh, doesn't feel obligated to tell the truth or explain or be correct on policy.
And I think, obviously, I don't want us to get the answer wrong, and a, the only reason to be in politics is to try to make a smart policy.
And I don't know how Democrats became associated with being stale, being stuck in the past, risk averse.
So I think in a lot of ways Democrats hamstring themselves by trying to get the answer right, trying to, uh, explain the problem, and don't remember to be funny, take risks, tell stories, and I think that that's why I'm running for Congress.
I don't think we need to forfeit social media following to the other side.
And I think that there's absolutely no reason that we can't be cool, fun, edgy, and break through, because at the end of the day, I think our policies are way more popular with the American people than the other side.
I mean, he is still one of the coolest dudes in the universe, so how that happened is something that I think people are trying to understand, and in many ways it's a branding and positioning exercise, because how did we lose that so quickly? I mean, we're talking about a decade.
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Quitting Biden, Proving A Point
He explains leaving the campaign altogether.
Fears For A Fair Election
He voices grave concerns about 2026 elections.
Democrats Lost The Cool
He challenges his own party’s instincts.
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