Why Does Trump Worship Dictators?

“Putin is very smart. He’s a genius. He’s taking over a country for two dollars’ worth of sanctions.” -Donald Trump on Vladimir Putin, Invader of Ukraine

“Your country is in big trouble. You’re not winning. You’re gambling with World War III. Dictator without elections.” -Donald Trump to Volodymyr Zelenskyy, the President of Ukraine

One invaded a sovereign democracy. The other is fighting to protect it. And Trump has made it painfully clear whose side he’s on, who he respects, and who he sees as a friend and ally, Vladimir Putin.

I’ve been thinking all day about the Crown Prince of Saudi Arabia, MBS’s visit to the White House, and the black-tie gala Trump threw for him afterward. The pageantry. The handshakes. The luxury. All of it paid for by the American people. And I keep coming back to the same question: When was the last time Trump stood beside someone who was on the right side of history? I’m not talking about performative alliances or transactional meetings. I mean a moment when he used the full weight of the presidency to honor someone who actually embodied what this country claims to stand for, freedom, courage, sacrifice, truth. Someone who made the world safer. Someone whose values reflect the best of who we are. I’ve looked for it. And I can’t find it.

What I see instead is a pattern. A president who goes out of his way to elevate tyrants. Who flatters strongmen. Who pardons criminals. Who surrounds himself not with the principled, but with the powerful, no matter what they’ve done. And it leaves me wondering what we’re becoming. Because this is not what American leadership looks like. Trump is most at home with the worst of us. He feels safer around murderers, dictators, and criminals than democratic leaders who can see right through him. He celebrates killers and bullies, then humiliates the people trying to hold their countries together. Because when he stands next to someone who earned their place through work, trust, and elections, the fraud is easier to see.

When Vladimir Putin shows up, Trump gushes. He praises the man responsible for bombing hospitals and kidnapping children. And when the Saudi Crown Prince visits, the one U.S. intelligence says ordered a journalist to be dismembered, Trump rolls out the red carpet. He hosts a black-tie dinner and brags about arms deals. In Trump’s version of events, Jamal Khashoggi wasn’t a murdered journalist; he was just “a very controversial man.” When asked about the killing, Trump shrugged, “Things happen,” as if the Saudi state-sanctioned murder of a U.S.-based journalist were an unavoidable accident. He didn’t just welcome Mohammed bin Salman. He glorified him, calling him “fantastic” and “brilliant,” and saying, “We have an extremely respected man in the Oval Office today, and a friend of mine for a long time, very good friend of mine.”

He wasn’t describing a democratic ally. He was praising the man who ordered Jamal Khashoggi suffocated, dismembered, and silenced forever. Audio recordings from inside the Saudi consulate captured Khashoggi screaming and gasping for air as the hit team closed in. His final words were “I can’t breathe.” Then he was injected with a substance, the screaming stopped, and the sound of a saw began, cutting through his body while his killers laughed. One advised the others to put on headphones or listen to music to drown out the noise. That’s who Trump calls “brilliant.” That’s who he throws a gala for.

American values used to mean something. The murder of a U.S.-based journalist once would have sparked bipartisan outrage. Now, it’s shrugged off. When Trump welcomed MBS into the White House, he didn’t just excuse the crime, he legitimized it. He told the world that if you have money, power, or oil, you can get away with anything.

But when President Zelenskyy shows up from a war zone, Trump turns cold. He scolds him. Interrupts him. Withholds military aid. Demands favors. And calls him “ungrateful” for not helping with Trump’s schemes. Same with Canada. When Prime Minister Justin Trudeau challenged Trump’s trade policies in 2018, which hurt both countries, Trump threw a tantrum. Leaving the G7 early. Called Trudeau “dishonest and weak.” Mocked him online. Threatened more tariffs. All because someone stood up to him with facts. And you have to wonder whether Trudeau stepped down after Trump was reelected because he didn’t want to deal with someone this volatile.

And the world sees it. They’re not just disappointed. They’re adjusting for survival.

Allies are quietly moving on. Defense officials are drafting contingency plans that assume the U.S. might not show up. Our allies are coordinating around us, not with us. Trade deals are being signed without American involvement. Sweden just signed a new strategic alliance with Canada. Their prime minister joked that Canada might now be Europe’s closest ally, but it wasn’t really a joke. It was a warning. Because it’s true.

Trump has made the United States unreliable. Erratic. Unmoored from principle. One day he’s shredding international agreements. The next, he’s praising tyrants and launching tariff wars against allies. It doesn’t follow strategy. It follows ego.

And I keep thinking: what happens when the next global crisis hits? A war. A pandemic. A nuclear standoff. When the world looks to America for leadership, will they find a steady partner? Or just another strongman, isolated, surrounded by sycophants? Or worse, will they not reach out to us at all?

They’re not pulling away to punish us. They’re doing it to protect themselves.

What Trump’s doing isn’t new. History has seen this play before.

In the 1930s, Hitler and Mussolini formed the Rome-Berlin Axis, not because they trusted each other, but because they feared the same thing: democracy. When Franco launched his fascist coup in Spain, it was Hitler and Mussolini who sent weapons and bombers, while democracies stood by, too afraid to pick a side. Authoritarians always find each other. Not out of loyalty, but out of shared cruelty. That’s the club Trump keeps trying to join. Not the circle of parliaments and presidents who answer to their people, the circle of tyrants, executioners, and kings.

And a reminder that it shows up here at home, too. Because Trump doesn’t just surround himself with the worst people, he unleashes them. He’s granted over 1,600 pardons. And on his first day back in office, he pardoned roughly 1,500 people connected to the January 6 attack. Not people who turned their lives around. Not those who showed remorse. He pardoned violent loyalists, corrupt allies, and dozens of insurrectionists who stormed the Capitol and beat police officers. At least 241 of them had assaulted law enforcement. Many didn’t go home to rebuild their lives. They reoffended.

Daniel Ball, convicted of domestic violence and assaulting police on January 6, was pardoned by Trump. After release, he was arrested again for illegally possessing a rifle and ammunition. This is who Trump aligns with. The people on the wrong side of history, and the wrong side of the law.

This is a message to the violent, the corrupt, and the cruel: Do it for me, and I’ll get you out. Loyalty, not law, is what matters. And psychologists say this isn’t random. It’s textbook behavior. Experts on narcissistic leaders have warned for decades: men like this cannot tolerate being challenged. They surround themselves with sycophants who protect their image at all costs, people who will lie, break the rules, and commit violence on their behalf. They create a bubble where no one challenges them, only flatters, obeys, or mirrors their emptiness. They surround themselves with people just as empty, so they never have to face the discomfort of decency or the quiet judgment of those who still have a conscience.

These leaders aren’t driven by strategy. They’re driven by insecurity. The praise of strongmen becomes a mirror, something to reflect back the power they don’t actually have. Trump doesn’t just admire these men. He needs them. Because he knows, deep down, they don’t respect him either. But as long as they flatter him, he can pretend. So when Trump embraces these men who depend on violence and fear, he’s building the only kind of world where he can survive.

And there’s something else. Something deeper. It’s not just wrong. It’s un-American. We were never perfect. We’ve failed at this before. Our hands aren’t clean. But there was at least the pretense of shame. The hope that we could be better. The belief, even if naive, that America should stand with the good guys. That we were supposed to try. Trump doesn’t even pretend.

That’s not American leadership. That’s abandoning the very idea of it. We used to teach our kids that America stood up to bullies. Now we have a president who is a bully.

And history tells us exactly where men like this end up. Authoritarians fall. Their cruelty gets recorded. Their names live on, in shame. But the democracies they mocked? They keep going.

Trump doesn’t know that part. Because he doesn’t study history. He just repeats it. But history always remembers who stood beside tyrants. And it remembers who spoke out while it still mattered.

The question isn’t whether Trump will fall. He will. The real question is how much damage we let him do before he does. And we have to remember: the only thing that stops men like him is a public that finally decides, this is enough.

I’ll see you tomorrow,
Heather

P.S. If you’ve made it this far, chances are we see things the same way. You can help keep this work going by subscribing to my Substack; there’s a free option, or you can become a paid subscriber for just $5 a month. Paid subscriptions help me reach more people, cover more ground, and keep telling the truth about what’s happening to our country.