Counterpoint: Jon Stewart Shouldn’t Run for President in 2028

But electing Jon Stewart as president would just lean into the skid. It would be an acceptance that the line between politics and entertainment is officially gone, and it would further our poisonous politics as a TV show that has led us to ignore the maintenance of our society to such a staggering degree that Trump and a college-aged doofus named Big Balls can overturn decades of American empire on a whim. Electing Stewart president is like trying to plug holes in a boat instead of just getting a new boat, but if that boat was the Titanic after it hit the iceberg.

I don’t know if Stewart would be a good president or not; that’s a nuanced and unknowable question. Last year I wrote tens of thousands of words about how ironic it is that the more conservative Joe Biden has a more liberal domestic policy legacy than Barack Obama (and how Obama is jealous of that fact), primarily due to how their clashing visions of governance manifest themselves in the real world. Obama is a classic technocrat who was very Trump-like in his desire to sit in the White House and let his advisors do the nitty gritty of politicking for him, while Biden is an old school back-slapper who loves to roll his sleeves up and go to war inside Congress. Biden’s form of politics was clearly more effective than Obama’s as he passed more substantial legislation with a smaller majority, and so answering those kinds of explicitly political questions that defined two presidencies are simply impossible when it comes to a man whose primary interaction with politics is cosplaying a journalist on TV.

I was one of those folks raised on The Daily Show and The Colbert Report, and while both shows hold a special place in my heart (especially the far superior Colbert Report), Stewart and Colbert’s famed debacle, The Rally to Restore Sanity and/or Fear, really crushed any belief I had in their viability as overtly political actors. It was a very classic vapid Democratic Party-esque message without enough detail to give people something to do with it, and the lack of any kind of follow through afterwards proves what a dud it was. Maybe if you put a serious political operation around them, their immense TV talents would make them viable candidates, and you can never ever discount anyone in this country with the most valuable commodity in politics: name recognition. But I have serious doubts about their abilities to command our political system.

A Stewart candidacy would be viable in a Democratic primary and possibly in the general election, but we are long past the point of “we need to find someone who can win elections.” Winning one presidential election will not fix this constitutional crisis. We need an LBJ or FDR-like figure who can lead an entire political project akin to Reconstruction, the New Deal and Great Society, where America spends decades amending itself into something resembling its founding ideals. Jon Stewart may be able to be the voice for something like that, but whether he could do the political groundwork to get Congress to pass revolutionary legislation is very much in question. Would he be willing to employ aggressive tactics like threatening the Supreme Court with expansion if they didn’t stop striking down his legislation like FDR did? Biden contrasted to Obama demonstrates that there is a political skill to doing politics (or in the case of Biden’s genocidal Gaza policy, not doing politics), and one of the best ways to develop this skill is to be embedded in politics, as Biden was for decades while Obama largely wasn’t.

Stewart is more thoughtful and articulate than the vast majority of Democrats, but just because the bar is six feet underground doesn’t mean we should just let anyone step over it. Why is Stewart a better candidate for president than say, J.B. Pritzker, a billionaire governor with a war chest that can go toe to toe with Trump’s? Especially when he is currently proving he’s willing to use it in innovative ways to help Texas Democrats resist this authoritarian redistricting overreach that proves the GOP’s interal polling sucks. Even the most cynical hairpiece the Democrats have in their rotation, Gavin Newsom, is demonstrating an understanding of his political power and is using it to resist Trump’s authoritarianism. Stewart could articulate the vision of using that power better than either governor could, but does he know how to actually use it?

Again, I would point those naturally assuming that a political commentator could easily do politics towards Barack Obama’s struggles to pass the platform he campaigned on. He barely had a cup of coffee in the Senate before becoming president, and his inability to command his own caucus is an indictment of this worldview which assumes that any schmuck can step into politics and be an effective political operator. Winning elections and enacting good policy are two entirely different skillsets, and while Stewart definitely has the ability to do the former, it’s very much a question whether the latter is in his wheelhouse. Politics is culture, but it’s not entertainment, and the inability to discern that difference is a big reason why Democrats cannot command real political power in America. Electing an entertainer as president would do little to push us off this hubristic track so many empires have followed into the dustbin of history before.