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.
U.S. President Donald Trump boards Air Force One on August 14, 2026 at Joint Base Andrews, Maryland. Trump is traveling to Long Island to tour law enforcement facilities in Nassau County and rally support for local Republican candidates ahead of the upcoming midterm elections
Travel Far Enough, You Meet Yourself
Is it possible that our President has simply not traveled enough?
Born and raised in Queens and attending Fordham University in the Bronx, Donald Trump has no record of traveling outside New York until he was over 20, when he transferred to a college in the neighboring state of Pennsylvania. Were his formative years amiss, then, in his learning about other places and other people?
Is his view akin to the famous New Yorker cover by Saul Steinberg, an illustration of the United States with New York City as the epicenter of the country and the Hudson River the border of the known world? We can now at least add Washington, D.C., and Mar-a-Lago to the map of “the realm.”
Our President has now traveled some, but what we recommend is another kind of travel. Not a state-sponsored trip or a venture to scout locations for future Trump Towers. This would be a genuine travel experience, enriching and eye-opening, showcasing other cultures and ways of living.
It will extend far beyond viewing military parades, hobnobbing with such “understanding” world leaders as Kim Jong Un, or taking tea with the King.
WHERE, then, should the President go? As Elon Musk’s Starship spacecraft is not yet ready to take passengers to Mars, perhaps he could explore our own vast country?
Maybe he could travel to “flyover country,” the farming states, where his ying-yanging tariffs and trade restrictions have played havoc with rural economies. Or possibly to California, number one in homeless U. S. citizens, and while there, regale homeless veterans (approximately 32,500 nationwide) with tales of his brave exploits invading and bombing foreign countries.
Or he might tour the Great Lakes, and rename the other four?
WHEN should he go? This will be tough, as he is very busy building his ballroom and renaming bodies of water.
How about a trip in early November, around the midterm elections? Despite the long-discredited accusation of widespread voter fraud, it would be reassuring to know he might be so caught up divvying out ladles of soup in a soup kitchen somewhere that he wouldn’t remember to deploy the military for “election security.”
HOW will he travel? He should definitely not take his Qatari-donated, newly renovated 747, especially after last time, when he had to be smuggled off clandestinely in a catering truck. It’s unlikely any traveling companions, like the Secretary of State or of the Treasury, are going to fall for the ruse a second time. Besides, we may need those people. No more decoys!
Perhaps the President could fly commercially, although this likely would expose him to undue suffering. Without gold bathroom fixtures and maple wood floors, the trip will be no “Luxury Experience.” If only he still had his “Trump Shuttle,” bought with a massive loan he later defaulted on, saying then, “I’m smart. I got out at a good time.”
Considering the potential pitfalls, maybe it’s best the President travel incognito, disguised perhaps as an elderly woman wearing a lot of bronzer.
Wherever, whenever, however: our President needs a vacation.
Moreover, we need a vacation from him.
If the President refuses our travel suggestions, here’s another idea:
Let’s get him a pet! He has never owned a pet. As we know with our children, pets teach essential life lessons: compassion and empathy; they instill a sense of responsibility. There is a well-established connection between those who can care for a pet and those who can care for people.
So, which pet should we choose? A puppy? A kitten? A boa constrictor?
Imagine, the President may even decide he likes having a pet. After all, what is more obedient than a well-trained dog, besides possibly the Cabinet? And what is more docile than a sweet kitten, other than plausibly the Supreme Court?
The President may even become more mellow with a pet afoot and less likely to slap tariffs on our allies, or attempt to annex our neighbors, or bully our Congress. (Realizing, of course, a bully requires active participation from the bullied to maintain his status.)
Maybe we should do both: get the President a pet and devise a travel plan for him. (Do you think we could possibly convince him to leave his phone at home?)
Let’s go for it! After all:
Travel far enough, you meet yourself. (David Mitchell)
And for our President, that would likely be the most profound discovery of all.
Amy Lockard is an Iowa resident who regularly contributes to regional newspapers and periodicals. She is working on the second of a four-book fictional series based on Jane Austen’s “Pride and Prejudice."