Dealing the Cards

By Nick Catoggio

Thursday, October 02, 2025

 

Kevin Williamson is almost always right, and I’m throwing the “almost” in there mainly because I think Mrs. Williamson might quibble if I didn’t.

 

But I sure thought he was right last week in how he interpreted the president’s latest bipolar episode on Ukraine. “After getting to know and fully understand the Ukraine/Russia Military and Economic situation and, after seeing the Economic trouble it is causing Russia, I think Ukraine, with the support of the European Union, is in a position to fight and WIN all of Ukraine back in its original form,” Donald Trump wrote.

 

That sounded promising! Then came the conclusion: “In any event, I wish both Countries well. We will continue to supply weapons to NATO for NATO to do what they want with them. Good luck to all!”

 

Kevin read that as a kiss-off, surmising that “Trump has had enough of the Russia-Ukraine war.” So did David Sanger of the New York Times. So did Tom Nichols of The Atlantic. And so did I. The president spent the first eight months of his second term trying to broker a ceasefire and achieved precisely nothing. Now, it seemed, he was washing his hands of the conflict. Good luck to all.

 

Bipolar episodes are called “bipolar” for a reason, though. Another disorienting mood swing is always right around the corner.

 

And here it was, arriving last night in the pages of the Wall Street Journal: “The U.S. will provide Ukraine with intelligence for long-range missile strikes on Russia’s energy infrastructure, American officials said, as the Trump administration weighs sending Kyiv powerful weapons that could put in range more targets within Russia.” The powerful weapons in question are Tomahawk missiles, which Volodymyr Zelensky has been seeking for ages.

 

Tomahawks have a range of 1,500 miles. As recently as six weeks ago, the Pentagon was preventing Ukraine from using any U.S.-supplied Army Tactical Missile Systems, which have a range of nearly 190 miles, to strike targets inside Russia. Now, suddenly, the United States is reportedly planning to help Kyiv zero in on those targets—and could make munitions available that would put Moscow itself within reach.

 

This administration is led by a guy who whined for two years that the Biden administration was courting World War III by supporting Ukraine’s resistance to Russia. Fast-forward to October 2025 and it sounds like he’s ready to help Zelensky bomb the Kremlin. Now that’s bipolar.

 

Not that I’m complaining. When Trump told Ukraine’s president during their infamous Oval Office meeting in February that his country can’t win because “you don’t have the cards,” every Reaganite in America had the same thought: So deal him some f---ing cards. Seven months and many, many, many Russian bombings later, the White House is finally shuffling the deck and allegedly preparing to deal. I’ll golf clap for that.

 

Still, we’re left with an unthinkable possibility: Could Kevin and I have been (gasp) wrong? Trump isn’t washing his hands of the Ukraine war after all? He’s actually … doubling down?

 

Maybe. There are three ways to read the Journal’s scoop.

 

Bad romance.

 

One theory is that it’s a bluff.

 

Trump’s posture toward Vladimir Putin is best understood as a “situationship,” I wrote in July, a romance that lingers indefinitely in ambiguity because the parties’ desires are mismatched. One yearns for a committed relationship and will never relinquish the fantasy that it might happen. The other has no intention of committing but sometimes hints that he does, because he enjoys the affection and wants it to continue.

 

For the committed partner, a situationship is an endless cycle of false hope and realistic despair (bipolar, one might call it) in which most of his or her time is spent strategizing on how to get the other to commit. Sometimes that strategy involves dialing up the affection. And sometimes it involves dialing it waaaay down.

 

Leaking to the Journal that the U.S. might start selling Tomahawks to Europe for Ukraine’s use is the equivalent of the committed partner making out with someone at a party in front of their beloved in hopes of sparking their jealousy. They’re not interested in the person they’re kissing, only in the reaction it might inspire. You’re losing me. Don’t you care that you’re losing me?

 

In fairness to the president, his would-be boyfriend has treated him quite badly since January.

 

Trump came into office promising to end the war. Per his “you don’t have the cards” dressing-down of Zelensky, he seemed eager to broker a deal that favored Russia. All he asked of Moscow up front was a 30-day ceasefire as a show of good faith. Not only did Putin refuse, he made the president look like a schmuck by increasing the volume of air attacks on Ukraine after Trump took office.

 

Sure, the Russian continued to drop occasional hints about commitment, like when he agreed to a date in Alaska. But date night ended early—and two weeks later, to underline his contempt for the White House’s peace efforts, he bombarded Kyiv. The president had already begun to develop a sneaking suspicion that Putin wasn’t really interested in him and this seemed to confirm it. The situationship had hit the skids, a romance gone bad.

 

So now here he is, making out with Ukraine at the party by threatening to help Kyiv destroy the Kremlin’s energy infrastructure. He probably doesn’t mean it, as it’s hard to believe that a nationalist postliberal committed to “ending endless wars” is about to start guiding Ukrainian bombs into Mother Russia. Doing so would contradict the new “America First” National Defense Strategy that Pete Hegseth is preparing, which reportedly calls for “centering the Pentagon on perceived threats to the homeland, narrowing U.S. competition with China, and downplaying America’s role in Europe and Africa.”

 

It’s a bluff designed to spook Putin and bring him back to the bargaining table, nothing more. (You don’t get real security commitments from Donald Trump unless you’ve given him a plane. Sorry, Zelensky.) Maybe it’ll work and Russia will hastily agree to resume peace talks. But if it doesn’t, we’ll likely end up with the same sort of empty threats from the White House that we’ve seen with sanctions, with the U.S. remaining forever two weeks away from supplying the Ukrainians with the intelligence they need to strike Russian targets.

 

The hallmark of a situationship is that it never truly ends. The door is always open to a reconciliation, even—or especially—when the committed partner gets desperate enough to suck face with others.

 

Everyone loves a winner.

 

Another theory is that Trump wasn’t just talking smack last week when he declared that Ukraine can win the war. He may be privy to intelligence that the Russian war machine is running out of gas.

 

Literally.

 

Don’t look now, but the world’s third-biggest producer of oil is experiencing gasoline shortages. Wholesale prices of fuel have risen more than 50 percent in Russia since January, forcing some regions to begin rationing. According to one analysis, more than a third of the country’s oil-refining capacity is currently offline. And higher gas prices have naturally contributed to high inflation, which as of August stands north of 8 percent and has led the Russian central bank to raise benchmark interest rates to, gulp, 17 percent.

 

Where’d all the gas go? A lot of it went up in smoke—thanks to Ukraine. Ukrainian drone strikes on Russian facilities are the main cause of the country’s declining refining capacity, it turns out, responsible for disabling 70 percent of the facilities that are presently out of commission. The war has come home to Russia, which has three great strategic virtues for Kyiv.

 

First, it’s demoralizing for the aggressor. Whether the Russian people might ever be willing and able to confront Putin is unclear, but a major fuel crisis is the sort of thing that could plausibly test their patience. Second, it’s paralyzing for the military. An army that can’t move can’t win, and Zelensky’s drone force is bent on depriving Russia of the thing its troops need to move. When you’re outgunned, wrecking the enemy’s logistics is the smart way to fight.

 

And third, expensive gas is another blow to a regime that’s already struggling to pay for the war. A poor economic forecast this week led the Russian government to announce new tax hikes, raising the value-added tax from 20 percent to 22 while drastically lowering the revenue threshold for businesses at which it will kick in. Despite that, the military’s budget is set to shrink slightly next year. Vladimir Putin just doesn’t have the cards, it appears.

 

Perhaps the president has come to realize that. And if there’s one thing he can’t abide, it’s allying himself with losers.

 

Donald Trump isn’t a stickler about attending his daily intelligence briefings, but he does seem to understand Russia’s predicament. In last week’s “good luck to all” statement, he wondered what might happen once the Russian people “find out what is really going on with this War, the fact that it’s almost impossible for them to get Gasoline through the long lines that are being formed, and all of the other things that are taking place in their War Economy. … Putin and Russia are in BIG Economic trouble, and this is the time for Ukraine to act.”

 

It would be out of character for him to behave rationally, but the case for putting the screws to Russia by beefing up Ukraine’s ability to target far-flung energy sites is now so compelling that even he may conceivably have been persuaded by it. You want to bring Putin to the table and end the war as soon as possible? Then give Zelensky what he needs to further starve the Russian military of fuel. To borrow the now-infamous words of his FCC chairman, Trump can end this conflict the easy way or the hard way. He tried doing it the easy way, by appealing to Putin personally. Now it’s time for the hard way.

 

Peace through strength, one might call it.

 

Frankly, NATO could use a display of strength from the United States right now. Last month, for the first time in the history of the alliance, NATO warplanes engaged Russian aerial weapons over a member’s territory. That happened in Poland; nine days later, three Russian fighter jets entered Estonian airspace and lingered until NATO fighters chased them off. Then, last Friday, mysterious drones were spotted over Germany and Denmark. It all has the feel of a test to see how the U.S. will respond to repeated provocations against an organization that our “America First” White House has never pretended to have much affection for.

 

Helping Ukraine hit targets in the Russian interior might be that response. I default to assuming personal motives in trying to divine Trump’s thinking—presumably he resents Putin’s attempts to make him look “weak”—but his awareness of Russia’s logistical problems might be influencing his decisions too. He won’t risk antagonizing a formidable enemy, but “a paper tiger,” as he described the Russian military in last week’s statement? Sure, he’ll get a little froggy with them.

 

The green light.

 

If either of the first two theories are correct, then Kevin and I are wrong about Trump giving up on the war. Under the first theory, he’s trying to bluff the Russians back to the table. Under the second, he’s planning to help Ukraine bomb the Russians into suing for peace.

 

But if the third theory is correct then we’re right. Under this one, the president really is washing his hands of the war—albeit doing it in a way that’s meant to put pressure on Russia.

 

Zelensky has wisely framed his request to the White House for Tomahawk missiles as a deterrent measure. “We need it, but it doesn't mean that we will use it,” he told Axios. “Because if we will have it, I think it's additional pressure on Putin to sit and speak.” That’s the way to reason with a guy who goes to bed each night dreaming of a Nobel Peace Prize.

 

It raises a knotty logistical question, though: If the U.S. gives Tomahawks to Ukraine, how will the Ukrainians fire them?

 

"The main launch platforms are combat ships or strategic bombers. We don’t have any strategic bomber aircraft," one Ukrainian government official reminded the Kyiv Independent. They don’t have much of a navy either. That means the missiles would need to be fired from land, which would require Typhon launcher systems. But Typhons are no ordinary piece of materiel.

 

“The United States only has two working Typhon batteries, with a third in progress,” military analyst Jennifer Kavanagh explained earlier this week. “Two of these systems are intended for use in Asia and one is earmarked for possible deployment to Germany.” The launchers are also huge and hard to maneuver, making them a ripe target for Russian attacks. And assuming that problem can be solved, Tomahawks themselves are in relatively short supply and needed for a potential Pacific conflict with China. Only a few allies have been allowed to purchase them. Even Israel has been told no.

 

We’ve all learned from hard experience that anything is possible in the Trump era. But our authoritarian leader arming a fledgling liberal nation with a prized weapon to counter Russian expansionism would be a genuine “huh” moment.

 

Almost certainly, then, the president isn’t going to give Zelensky any Tomahawks. Yet the fact that he’s willing to entertain the request publicly is worth something in itself.

 

That’s because other Ukrainian allies are willing to provide the muscle for strikes inside Russia. “Very shortly, very soon,” German Chancellor Friedrich Merz said in July about supplying long-range weapons to Ukraine. The U.K. and France, meanwhile, gave Kyiv permission to target Russian sites nearly a year ago. Until this week, that seemed like the sort of thing that might potentially fracture NATO: Given Trump’s worries about World War III and his interest in midwifing a peace deal, one could imagine him warning Zelensky and the Europeans that the U.S. won’t tolerate a bombing campaign in the Russian interior that risks escalating the war.

 

Tuesday’s Wall Street Journal scoop might be the White House’s way of putting Moscow and Europe on notice that, on second thought, the president will tolerate that. He’s not giving Ukraine Tomahawks, and he may or may not follow through in providing intelligence on targets, but if the Ukrainians and their European allies want to bomb Russian refineries all over the map? Go nuts.

 

Trump may be done with the war, that is—and he’s also done with restraining NATO’s side of it. Ukraine and its allies have the green light to hit Russia. That’s what Putin gets for not taking peace seriously when the president gave him the chance.

 

The sticky wicket here is what happens if Putin responds to Ukraine’s long-range attacks by striking the NATO allies who supplied the missiles. Yes, that would be irrational, as an army that’s hurting for fuel and floundering against Zelensky’s forces is in no position to drag Poland and the Baltics into the fight. But staging air incursions into Poland, Estonia, Germany, and Denmark at this stage of the war isn’t very rational either.

 

A Russian nationalist who’s spent his adult life obsessed with avenging defeat in the Cold War and who’s already bet his legacy on the Russian military's ability to overcome any hardship might act unpredictably as the odds against him rise. Putin hasn’t managed to split Trump from NATO by flirting with him or by pulverizing Ukraine on the battlefield. He might reason that his last, best chance is to test the president’s commitment to Article 5 directly.

 

Probably not, though. Again, situationships are never really over: All it takes is a little flirting and hints of commitment to make things right. My guess is that Putin will figure out a way to make Trump fall in love again before any Tomahawks start falling on the Kremlin.