Closing in on nine years as president of the Institute for Free Speech, David Keating long ago cemented his status as one of the foremost conservative forces in the money-in-politics debate. The nonprofit's aim is to safeguard First Amendment rights, particularly unfettered political speech, and views deregulation of campaign finance as central to that goal. Keating took charge after a similar group he started, SpeechNow.org, won a federal lawsuit to end donation and spending limits on independent political groups — thus creating super PACs. He had top posts at two prominent fiscal conservative organizations, the Club for Growth and the National Taxpayers Union, earlier in a D.C. advocacy career dating to the 1980s. His answers have been edited for length and clarity.
What's democracy's biggest challenge, in 10 words or less?
Stopping government from discouraging dissent.
Describe your very first civic engagement.
In high school, I learned about machine politics. My friends who wanted to become summer lifeguards had to be Republicans. I thought that was ridiculous, so I decided to register as an independent. Still am.
What was your biggest professional triumph?
Being appointed in 1996 to the National Commission on Restructuring the IRS, a bipartisan group of tax experts. We surprised many when we reached a broad consensus. Unlike most such reports that gather dust, ours was turned into a bill that became law. It included my recommendations to strengthen taxpayers' rights when interacting with the IRS and to protect innocent people from being forced to pay taxes owed by any tax-cheating former spouses.
Many of my most rewarding experiences have come in volunteer work. Ten years ago my SpeechNow won the case allowing independent groups to fundraise freely. This year I became a director of Masks4All and saw 85 percent of the nation adopt mask requirements to fight Covid-19.
And your most disappointing setback?
Failure to advance through Congress a constitutional amendment requiring a balanced federal budget. Two times in the 1990s we came up just one vote short in the Senate. Still, our campaign helped spur the first annual budget surplus in nearly four decades, starting in 1998 and lasting until the Sept. 11 attacks.
How does your identity influence the way you go about your work?
I identify as an independent person. I'm a registered independent in part because I don't trust either party on key issues. Too many people focus too much on "what's best for my team," either red or blue, which affects their ability to think clearly.
To promote and defend independent thought, much of my professional work has been protecting the freedoms to speak, publish, join groups and petition government for redress of grievances. Without these freedoms, we can't obtain the information we need to understand the world or act effectively to make it a better place.
What's the best advice you've ever been given?
Be a lifelong learner.
Create a new flavor for Ben & Jerry's.
Freedom of Peach.
What is your favorite TV show or movie about politics?
"One Flew Over the Cuckoo's Nest," the 1975 Oscar winner for best picture, about rebellion in a mental institution.
What's the last thing you do on your phone at night?
Turn on the bedside clock app.
What is your deepest, darkest secret?
I think Dave Chappelle and Anthony Jeselnik are hilarious. But don't tell my wife.
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.