There looks to be a new twist in the decades of voter ambivalence toward those rich enough to finance their own campaigns: For former Starbucks CEO Howard Schultz, being a billionaire seems to be more of a hindrance than a help as he ponders seeking the presidency as an independent.
In the cases of both Mitt Romney (who spent $45 million of his own fortune as the GOP nominee in 2012) and Donald Trump (whose $66 million investment was just one-fifth of what his campaign spent in 2016), "there were only muted complaints about the unfair advantages of being a candidate who could hold a fund-raiser staring at the mirror in the morning," veteran political analyst Walter Shapiro writes for the Brennan Center for Justice. "That's why the widespread scorn for Schultz's initial foray into the 2020 race marks an unexpected change in public attitudes towards self-funders."
Running on a deep-pocket, I-can't-be-bought platform has its limits, however, he notes with this important nugget of campaign finance analysis from the 2018 midterms: 19 congressional candidates who spent more than $1 million of their own did not get past the primaries. "The anti-Schultz onslaught may have a far larger meaning than the fate of his individual candidacy. Because of Buckley v. Valeo, social disapproval is the only weapon available to deter billionaires from dominating politics."
image of U.S. President Donald Trump is displayed on a digital billboard in Times Square in New York on April 8, 2026.
Trump is stuck between two realities. Neither serves the American people
Normally, I worry that events may overtake a column. But not so with the Iran war.
I don’t worry about running afoul of a headline or Truth Social post from the president because what is said about the situation is no longer very relevant to the reality.
On April 8, Nick Catoggio, my Dispatch colleague, dubbed an earlier stoppage with Iran “Schrödinger’s ceasefire.” This was a reference to the famous thought experiment by the physicist Erwin Schrödinger, who was trying to explain the weirdness of “superpositionality” in quantum physics. A cat in a box is both dead and alive at the same time until you open the box. Schrödinger meant to illustrate the absurdity of the idea that particles aren’t any one thing, but a “cloud of probabilities.”
The Trump administration is stuck in a word cloud of probabilities of his own making. The war is over. The war is on. The war isn’t a war. We have a deal, but we don’t have a deal, but we’re about to have a deal. We destroyed Iran’s military. No, we left it intact. We want regime change. No we don’t. We already accomplished it. We “obliterated” Iran’s nuclear program a year ago. We had to go to war in February to prevent nuclear war. The Strait of Hormuz is open, closed, or something in-between. No deal without “unconditional surrender.” Let’s make a deal!
This everything-all-at-once vibe can be disorienting, particularly since most Americans didn’t have a war with Iran on their bingo cards until the shooting had already started. President Trump didn’t prepare the country or consult with Congress beforehand because he thought it would all be a smashing success in a matter of weeks.
The miscalculation that started it all: killing Iran’s Supreme Leader, Ayatollah Ali Khamenei, and much of Iran’s senior leadership, on the first day of the war. To “the great proud people of Iran, I say tonight that the hour of your freedom is at hand,” Trump announced on Feb. 28. “When we are finished, take over your government. It will be yours to take. This will be probably your only chance for generations.”
I support regime change in Iran and shed no tears for Khamenei or his goons. But when you start a war by killing the regime’s top leaders, it’s not unreasonable for the remaining ones to conclude that you really intend regime change.
Khamenei was a murderous fanatic, but he was a fairly cautious one. He liked to threaten closing the Strait of Hormuz or attacking our regional allies, but he was reluctant to actually do it, fearing it would invite a regime change war. The mullahs and IRGC goons believed, not unreasonably, that if they lost their grip on power, they’d be lynched by the Iranian people they’ve brutalized for decades.
By starting with a regime change war, Trump removed any reason for the regime not to go for broke. When you have nothing to lose — particularly when you are a millenarian religious fanatic — a Persian Alamo strategy makes a lot of sense.
So Iran closed the Strait of Hormuz and attacked its neighbors.
But it turns out this wasn’t the Alamo. In the contest of wills, Trump blinked. The Iranian regime’s tolerance for punishment proved — so far — to be greater than Trump’s and that of our gulf allies. Militarily we could finish the job, but that would require ground troops and much greater economic turmoil. In a conflict Trump launched unilaterally without the prior support of Congress, NATO or the American people, Trump doesn’t have the political capital for that.
But that’s only half the problem. Trump wants the war over, but he doesn’t want to pay — militarily, economically, politically — what that would cost. So he wants to make a deal that ends it. But there is no deal available that wouldn’t come at an equally undesirable cost. Any deal that looks like what President Obama struck with the Iranians would be too embarrassing to bear. But the Iranians are convinced that they can get just such a deal, and they’re willing to drag things out as long as it takes.
The result: Trump’s in a box of his own making. He thinks he can talk his way out by simply asserting a reality that doesn’t exist. When the financial markets get nervous, he announces a breakthrough that is, at best, a possibility. When the Iranians agree to a deal that looks similar to one Obama might negotiate, Trump goes back to his threats.
It can’t go on forever. But I’m sure it’ll last until long after this column is forgotten.
Jonah Goldberg is editor-in-chief of The Dispatch and the host of The Remnant podcast. His Twitter handle is @JonahDispatch.