Surprise! Trump Is Selling Ukraine Down the River

August 25, 2025

What is wrong with this picture?

Everything.

So Happy Together/photo credit: Getty Images

The tall guy is the head of the oldest democracy in the world. The short guy is a ruthless dictator whose army has invaded a democratic nation and killed thousands of its civilians. He is a war criminal. The tall guy should not even meet with the little guy, but he seems absolutely delighted to see him.

The tall guy is President of the most powerful nation in the world, with the largest economy and the strongest military. The short guy presides over the #11 economy, which is struggling because of the war he started. Texas has a bigger economy than Russia. The little guy’s army has suffered 600,000 casualties in three years, and it must buy weapons from Iran and North Korea.

But Donald Trump defers to Vladimir Putin and lets him dictate the terms of a possible “deal” for Ukraine. Can you imagine any other American President doing that?

A Neville Chamberlain for Our Times

If this were 1941, Trump would tell Winston Churchill, “Face it, Winnie, the U.K. is a tiny island. Make a deal with Hitler while you can, he’s not so bad. You just don’t have the staying power… or the money to pay for all the weapons you need to buy from us.”

Trump met with European leaders in Washington, before he flew to Alaska for his summit with Putin. The Europeans insisted, and Trump agreed with them, that Putin must accept a cease-fire as a precondition to any negotiations with Ukrainian President Volodymyr Zelensky. Trump loudly declared that he would not be “happy” without a cease-fire and that he might levy heavy economic sanctions on Russia if he did not get one.

Then, in Alaska, he caved immediately, claiming that a cease-fire was no big deal. Trump held a strong hand of cards, but he folded.

Dangerous Ignorance

Trump, an ignorant man, does not know the history behind the Russia-Ukraine war. Ukrainians have “voted” overwhelmingly three times in the last 35 years for independence from Russia: a referendum in 1991, which separated Ukraine from the Soviet Union; the Orange Revolution (2004-05); and the Maidan Revolution (2014).

Although many people in the Donbas and other regions in eastern Ukraine speak Russian, they consider themselves Ukrainian. Zelensky spoke Russian as his mother tongue before becoming President.

Trump treats the war between Russia and Ukraine as a real estate transaction: each side swaps some land and there’s a “deal”. Trump does not refer to a “peace agreement”, an “accord”, or a “treaty”. For him, it’s just another transaction.

His chief negotiator on Ukraine (and Gaza) is Steve Witkoff, a real estate investor and manager who has no previous experience in diplomacy. Witkoff tends to repeat the Kremlin’s talking points, such as blaming NATO’s expansion for causing the war. That’s wrong. Trump also echoes Russian propaganda; he has even blamed Zelenksy, not Putin, for starting the war.

Amateurs Playing in the Big Leagues

The US is fielding a C team against an A team. Putin has been plotting to take over Ukraine since he came to power 25 years ago, as he pursues his dream of restoring the Soviet Empire. Trump thinks he can wing it at a hastily improvised summit. Putin and his team have studied Trump and prepared assiduously for their discussions with him.

Furthermore, Trump and Witkoff are flying blind. Trump has conducted massive purges of the State Department and the intelligence agencies. He has driven out the talented officers and analysts who understood the Russians and the facts on the ground in Ukraine. They could have educated Trump and Witkoff on the issues and briefed them on dealing with Putin (if Trump would have listened.)

Russia’s Outrageous Demands

Putin has set several outrageous conditions for a “deal”. Among them, he has demanded that Ukraine surrender all the Donbas region, including areas that the Ukrainians still control. Trump should have rejected that proposal out of hand, but he seems to consider it reasonable.

Trump apparently does not know—or perhaps he does not care--that the Ukrainian-controlled parts of Donbas are heavily fortified and are key components of Ukraine’s defenses. That is precisely why Putin wants Zelensky to give them up. If Ukraine is forced to abandon these positions, the Russians might sweep beyond the Donbas and conquer much more Ukrainian territory.

Trump evidently also does not know, or care, that the remaining parts of the Dombas are rich in mineral resources, which are important for Ukraine’s economy. These areas are also populated by 200,000 Ukrainians, who do not want to live under Russian rule. They have heard about the atrocities the Russians have committed in the Donbas zones that they occupy.

Hollow Words

Trump wrings his hands about Russia’s attacks on Kyiv and other Ukrainian cities, saying, “The killing has to stop”. But Trump’s words ring hollow; he does not blame Putin or take any concrete action to help the Ukrainians. This is like Republican politicians who respond to mass shootings in the US by offering their “thoughts and prayers” to the victims’ families…and then do nothing to stop the violence.

Trump is repeating history in a very bad way. In his first term, he was so eager to end the war in Afghanistan that he agreed to exclude the Afghan government from the negotiations. That decision had a terrible impact on the Afghans’ morale, of course, and it prevented them from objecting to unreasonable demands by the Taliban. In effect, Trump negotiated a surrender agreement and presented it to the Kabul regime as a fait accompli. He set the stage for the disastrous US withdrawal, although Joe Biden bears some responsibility, too.

Trump wants to end the Russia-Ukraine War for petty, personal reasons, not to help the Ukrainians. He is obsessed about being winning the Nobel Peace Prize. Why? Because Barack Obama received that honor, and Trump is jealous. So Trump is rushing to get a “deal”, any deal, in his campaign for the Prize.

A Strong Offense Is the Best Defense

If Trump were serious about ending the fighting in Ukraine, he could take several steps to pressure Putin:

· Demand that the Ukrainians be included in all meetings and negotiations

· Insist on a cease-fire freezing the current battle lines

· Send more weapons and money!

• Ask Congress to approve a new support package for Ukraine…and double the ante, from $60 billion a year to $120 billion

• Ramp up production of US air-defense systems for Ukraine

· In concert with European allies, start liquidating the $300 billion of frozen Russian assets held in Western banks and give the money to Ukraine to rebuild damaged areas

· Authorize Ukraine to use US long-range missiles for strikes inside Russia

Besides these concrete actions, Trump must stop bashing our NATO allies. Trump must reaffirm in the strongest terms America’s commitment to defending them against a Russian attack. That would make Putin sit up…and perhaps take another look at his cards.

But instead, Trump will probably continue to sabotage President Zelensky and the Ukrainian cause.

Why Abandon Ukraine?

Why is Donald Trump so enthralled by Vladimir Putin? Why doesn’t he want to defend a fellow democracy?

First, let’s talk about the elephant in the room. Putin might have some hold over Trump because of “compromat”, KGB slang for “compromising information”, although that has never been proven. Trump was in dire financial straits in the 1990s, after a series of bankruptcies, and American banks would no longer lend him money. He may have sought and obtained Russian financing for a hotel/condo he built in New York’s SoHo district, though there is no public evidence of that.

Trump had an unusual relationship over the years with Deutsche Bank. The bank was investigated for possible money laundering on behalf of Russians in Europe. Trump was also well acquainted with a shady Russian businessman, who rented an office in Trump Tower and had contacts with the Russian Mafia in New York and Russian investors.

Some observers have suggested that the Trump Organization helped Russians to launder money by purchasing apartments in its buildings. That has also never been proven, and Trump has repeatedly denied that he had any business dealings with “Russia”.

Second, Trump is probably still furious with Zelensky because he refused Trump’s request to hurt Joe Biden’s 2020 presidential campaign by accusing him (falsely) of corrupt dealings in Ukraine. For Trump, punishing Zelensky may be more important than protecting Ukraine and, in the long term, our NATO allies against Russia’s aggression.

These are possible, intriguing factors. However, there may be more fundamental, sinister, reasons for Trump’s subservience to Putin and indifference to Ukraine’s suffering.

Putin Envy Syndrome

Trump seems to envy Putin, and to admire him, because the Russian has total control of his government and his country. Putin does not have to deal with pesky journalists, critical academics, or politicians from an opposing party. Putin does not have to worry about winning elections. Putin has created the kind of strongman rule that Trump wants to establish in the US. Russia is the model that Trump wants to follow.

Putin has also reportedly become very, very rich since he came to power. Russian oligarchs know that they must share their wealth with Putin to stay on his good side. This type of arrangement undoubtedly holds great appeal for Trump, who has already enriched himself considerably in his second term.

Autocrats Sticking Together

Since Trump is an autocrat by nature, he is not interested in preserving Ukraine’s democracy. To the contrary, he understands why Putin wants to snuff out a democratic country that borders Russia. Ukraine poses a threat to Putin’s tyrannical regime, simply because it is a free, capitalistic society right next door. Before the invasion, ordinary Russians may have been jealous of their “Ukrainian brothers”, who were free to vote or protest and were on a path to closer integration with the West.

Furthermore, Trump is a sociopath; he does not have empathy. As a result, Trump does not care about the 300,000 casualties that Ukraine has suffered because of Putin’s invasion.

It’s possible that Trump will surprise everyone and negotiate a reasonable cease-fire that freezes the current conflict along the current battle lines. Trump might step up and commit to helping Ukraine rebuild its military and restore its cities.

But don’t bet on it.

The Wall Street Democrat.