A Tale of Trump’s Wrongdoing and The Contrarian's Pro-Democracy Pushback

 

Two weeks of Donald Trump’s war on Iran, this much is clear: It is a colossal foreign policy blunder. The Iranian leadership seems substantially intact with another, and reportedly more fundamentalist, Khamenei at the helm. Collateral conflicts have been set off across the region, with hundreds of civilians and 13 U.S. service members dying. 

The Strait of Hormuz has been mined and turned into a missile proving ground. The price of oil soared to over $100 a barrel, staggering the world economy and worsening the affordability crisis for American families. For Americans, it’s among the most unpopular commencements of a war ever. And with no endgame in sight, Trump’s low polling numbers are likely to meet the same fate as oil shipping traffic: continued bombardment.

Iran is certainly the worst of Trump’s foreign policy fiascos, but it by no means is the only one. Indeed, there have been so many that it’s hard to keep track. That’s why I decided for this week’s column, I would catalog Trump’s Top 10 foreign policy failures as the latest entry in our Contrarian Top 10 lists. I drew on my experience as a U.S. ambassador among many other sources (including colleague Jen Rubin’s own version of this list for 2025).

As you will see when you look at the list, this is not only a tale of Trump’s wrongdoing – it’s also the story of our pro-democracy pushback. Despite the difficulty of litigating foreign policy snafus, with your support we have often found a way to do that in the courts of law as well as, of course, in the court of public opinion, including through our coverage here at the Contrarian. You make all of that possible with your paid subscriptions.

1. Insane Iran Illegalities

In a matter of days, Trump has somehow managed to combine the worst aspects of our most foolish wars, from Vietnam to Iraq. It is also outlandishly illegal, as I explained with a bipartisan group of experts last week in the Contrarian. We are working up a litigation rejoinder — stay tuned!

2. Terrible Tariff Troubles

Trump’s erratic and ill-defined tariffs policy has alienated allies, shaken the global reputation of the U.S. economy, and penalized millions of American small businesses and working families with an illegal tax, as the Supreme Court recently ruled. Because there is an enormous amount of damage to rectify, Democracy Defenders Fund and our wonderful partner Platkin LLP have filed a lawsuit against the government over the collection of tariffs imposed under the International Emergency Economic Powers Act. We will fight to recover funds that were unlawfully seized from our wonderful client Busy Baby LLC and its owner Beth Benike, fighting on behalf of all small businesses. And I hosted New Jersey Attorney General Matt Platkin and Benike at the Contrarian this week:

3. The Maduro Mess

Trump’s trial run on regime changes unilaterally began in our own backyard. Two months ago, the United States launched strikes against the Maduro regime, seizing Venezuelan President Nicolás Maduro in the process and bringing him and his wife to the United States for trial. Whatever you think of that end, it should not be achieved by illegal means. At DDF, we filed a bipartisan ethics complaint from our all-star team of ethics experts, representing the Clinton, Bush and Obama administrations, seeking an investigation of the lawyers at the Office of Legal Counsel who gave the wrong legal advice.

4. Maritime Massacres

The illegal use of power in Latin America began with strikes on boats in the Caribbean and the Eastern Pacific that the administration claimed to be carrying drugs. Not only does it appear that some people on these boats may have been innocent civilians, but, even worse, defenseless survivors were apparently killed. We at DDF make sure that the rule of law is applied to everyone, and I, alongside fellow ethics experts Ginny Canter and Richard Painter, filed a complaint at the Justice Department demanding that this illegal advice be exposed to the public.

5. Undermining Ukraine

​​Despite Trump claiming he’d negotiate peace between Russia and Ukraine within a day of taking office, the war between Russia and Ukraine has only intensified under his watch. In fact, 2025 was the deadliest year for civilians in Ukraine since the war began. For President Volodymyr Zelensky, Ukraine, and Europe, Trump has been the worst of allies. That has sent a message to our friends everywhere that we cannot be trusted. But fortunately Trump does not speak for all Americans, and he certainly does not speak for the Contrarian, where we have been vocal in standing up for Ukraine and for American alliances.

6. Greenland Greed

Trump’s obsession with treating sovereign nations like real estate is nothing new. In his first term, he tried to buy Greenland — an idea that was quickly shot down by the Danish government. This time around, he decided to send Donald Trump Jr. to advance the deal in Greenland, during which the junior Trump met with locals with a message from his father promising that the United States would “treat [Greenlanders] well.” Unsurprisingly, Denmark and the rest of our NATO allies rejected the offers resoundingly.

Ultimately, at the World Economic Forum, NATO General Secretary Mark Rutte and Trump announced a “framework of a future deal” that would renegotiate American military presence in Greenland but ultimately prevent the United States from acquiring the territory. As I told the Organized Crime and Corruption Reporting Project, the absurdity of acquiring another sovereign nation’s territory is only “made worse by allegations that Trump[’s] associates have ties to companies who could benefit from the president’s actions.”

7. Undoing USAID Unlawfully

The complete gutting of the U.S. Agency for International Development has been nothing short of catastrophic. Once one of the world’s largest funders of disaster relief, food security, clean water, and disease prevention — credited with saving more than 90 million lives over two decades — it has been all but dismantled. According to estimates from Boston University epidemiologist Brooke Nichols, more than 500,000 children died in the first year alone as a direct result of these cuts. This is abhorrent — a betrayal of every principle we claim to hold.

We at DDF were the first to sue over Elon Musk’s actions through DOGE and the legality of his appointment. The case is ongoing, and we are now fighting to take his deposition and prove the wrongdoing. We won’t stop until justice is done.

8. Canada Clown Show

Trump’s repeated attacks on our ally Canada are unhinged. He has battered our peaceful neighbor with a series of erratic tariffs, publicly ridiculed Canadian leaders, and even joked about taking over the country and making it the 51st state. In doing so, he has squandered the goodwill Canadians have long held toward the United States, turning a trusted partner into a wary skeptic increasingly inclined to distance itself from us. Just ask the bourbon industry — and many others.

9. A Chinese TACO

By contrast, Trump seems never to have met a dictator to whom he won’t kowtow. One of the more humiliating examples was his about-face on China. His initial tariffs on that nation were met with pushback, setting off an escalating trade war. Unfortunately, Trump neglected the fact that we need China’s rare earth minerals for a wide variety of U.S. uses. China cutting off those exports brought Trump to his knees. He ultimately made concessions, including dramatically cutting back the tariffs he had imposed. Who knew that TACO was Chinese food?

10. Voiding Voice of America

Voice of America and other U.S. government global media have long been crown jewels of American soft power around the world. Countless people have relied on the news our nation provides, particularly where free media is scant. As a former ambassador in Prague, I know this well. So many foreign friends told me how they counted on “the radios” broadcasting VOA and more.

Over the past year plus, that has been systematically dismantled, profoundly affecting our interests and reach as a nation. Here, too, with wonderful partners and clients, my democracy litigation colleagues and I have pushed back, with win after win. Most recently, we secured a court order that Kari Lake’s appointment as interim CEO of the U.S. Agency for Global Media was illegal and her actions invalid. The battle continues – thanks to your paid subscriptions.

11. Bonus: Donald’s Domestic Defeats

Of course, in a sense, all of our 267 legal cases and matters help counteract Trump’s foreign policy fiascos. That is because domestic victories also act as guardrails on Trump’s power, preventing him from veering even further off the rails. Conversely, when our allies see that the rule of law is holding, they are reminded of what really makes America great and that our nation will be back.

-The Contrarian