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.
A golden tray sits on the Resolute Desk as President Donald Trump speaks during an announcement on American nuclear innovation in the Oval Office at the White House on July 24, 2026, in Washington, D.C. Trump is signing multiple executive orders targeting the nuclear energy sector and easing rules for new reactors and nuclear fuel supply chains.
Trump’s hubris rivals the fallen heroes of ancient Greek mythology
In January, the New York Times asked President Donald Trump if there were any limits on his global powers.
“Yeah,” the president responded, “there is one thing. My own morality. My own mind. It’s the only thing that can stop me.”
That was eight months ago, but fortunately Christopher Nolan’s blockbuster adaptation of “The Odyssey” has made ancient Greek literature newly relevant. Before that window closes, I’d like to talk about hubris.
Today, the term mostly means excessive pride or arrogance. That’s part of what the Greeks meant by it too, but the meaning was a bit richer and more specific. Hubris was an insolent or outrageous act that offended the gods, often because the transgressor was claiming abilities or authorities that solely belonged to supreme beings.
Nolan renamed and slightly modified the concept of xenia for the film, calling it “Zeus’ law.” In the director’s telling, mortals should follow the rules laid out by the gods, specifically the requirement to treat strangers with respect lest they be gods in disguise.
In a sense, hubris is the opposite, or at least the rejection, of xenia. The hubris of the suitors, and at times Odysseus himself, invites punishment by the gods and their mortal instruments.
Which brings me back to Donald Trump. His claim that there are no constraints on his personal power to dictate events on the global stage was one of the greatest expressions of hubris ever uttered by a political leader.
Trump’s claim was obviously false when he made it.
He vowed that he could end the Russia-Ukraine war in 24 hours. He’s proved powerless to make that happen. If he had divine powers to work his will, why would he have balked at implementing his tariffs so often that Wall Street adopted the “TACO trade” term for his deals? “TACO” stands for “Trump always chickens out.”
And why would Trump have made so many embarrassing concessions to China — from rescinding tariffs on Chinese goods to allowing them to buy crucial and incredibly valuable computer chips?
But Trump saw his success at capturing Venezuelan strongman Nicolas Maduro as proof of his ability to launch missiles to the same effect as Zeus’ lightning bolts. Trump believed he was the most powerful man who ever lived.
This is no exaggeration. In March, when the Iran invasion seemed successful, Trump gave a document penned by“Presidential Historian David King” to New York Times reporters Maggie Haberman and Jonathan Swan purporting to prove that Trump was “the most powerful person to have EVER walked this planet.” King was, in fact, a businessman and occasional caddy for legendary golfer Gary Player.
King compared Trump favorably to many of history’s most powerful, and often heinous, figures: Alexander the Great, Attila the Hun, William the Conqueror, Napoleon Bonaparte, Joseph Stalin, Genghis Khan, Mao Tse Tung, Adolf Hitler and Vladimir Lenin. Many of these men thought they were the most powerful person in the world, too. And many were defeated precisely because they believed it.
At least Napoleon and Hitler had a string of truly impressive victories before they learned the folly of hubris. The limits on Trump’s power have been exposed by far less august forces than the combined might of the allies in World War II or the fearsome Russian winter.
Iran is a comparatively middling power. But the regime’s ability to absorb punishment while imposing its will on the Strait of Hormuz has proved to be a greater constraint on Trump’s power than his morality or mind. We should note that, at least rhetorically, his morality has not proved much of a constraint. He has repeatedly promised to destroy Iranian “civilization” if the regime refuses to capitulate.
But they haven’t — and won’t anytime soon — because the regime’s tolerance for pain far outstrips Trump’s. The combined fear of skyrocketing oil prices, outrage of Gulf state potentates, diminishing weapon supplies and domestic unpopularity is doing the work that international law, congressional oversight and the collective opinion of foreign policy experts can’t or won’t do.
If I considered Trump more heroic than reason and facts could allow, I would say his Sisyphean predicament has the whiff of Greek tragedy to it. Trump is vexed by the fact that the Iranians won’t honor deals or ratify his countless premature claims of victory — giving new meaning to his vow that his presidency would make people tired of winning. It’s almost like they’re out-Trumping Trump.
Things might have gone better if he’d heeded that great Greek tragedian Sophocles: “For Zeus utterly abhors the boasts of a proud tongue.”
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Jonah Goldberg is editor-in-chief of The Dispatch and the host of The Remnant podcast. His Twitter handle is @JonahDispatch.