It's the question that won't die. Walk into any bar or scroll through any social feed today, and you’ll hear it: is he actually on their side? Honestly, the answer isn’t a simple yes or no, no matter how much people want it to be.
If you look at the headlines coming out of early 2026, things are getting weirdly intense. We’ve got a president who says he can end the war in Ukraine in twenty-four hours, yet he’s often seen pointing the finger back at Kyiv. Just this January, Trump told Reuters that Ukrainian President Volodymyr Zelenskyy is the one "having a hard time" getting to a peace deal. He basically suggested that Vladimir Putin is ready to sign on the dotted line, while the guy whose country is being invaded is the holdout.
It feels upside down.
The "Peace" Push and the 20% Problem
Right now, the big talk in Washington and Davos is about this "basic document" to end the war. Trump’s envoys are scurrying around, meeting with everyone, trying to hammer out a schedule. But here is the kicker: the reported "breakthrough" moment happened when American officials realized Zelenskyy might have to give up roughly 20% of his country.
Trump’s advisers—real estate guys at heart—reportedly look at those disputed territories in the Donbas as "trim" or "doorknobs" in a massive property deal. They think it's a sliver of land nobody in America has ever heard of. But for Ukraine, it's their home. It's their sovereignty.
This is where the "siding with Russia" talk gets its fuel. If you’re forcing the victim of an invasion to give up land to the aggressor to make the fighting stop, are you being a peacemaker or just an accomplice?
What the Critics See
The list of "pro-Russia" moves is long, and honestly, pretty consistent over the years. You’ve got:
- The constant praise for Putin’s "genius" and "strength."
- Threats to pull the U.S. out of NATO or stop defending allies who don't pay up.
- That infamous moment in Helsinki where he seemed to trust Putin over his own intelligence agencies.
- The 2025 National Security Strategy, which basically stopped calling Russia an "acute threat."
Critics like Craig Unger argue this goes back decades. They claim Soviet operatives identified Trump’s ego as a "weakness" back in the 80s. The theory is that by bailing him out when banks wouldn't and showering him with flattery, they built an "asset" who does their bidding voluntarily. Whether you believe that or not, the rhetoric often mirrors the Kremlin’s own talking points.
The "Tough on Russia" Counter-Argument
Now, hold on. If you talk to Trump’s supporters or former Cabinet members, they’ll tell you the "siding with Russia" narrative is a total fabrication. They point to the actual policy—not the tweets or the off-hand comments at rallies.
Basically, they say he’s been tougher on Russia than Obama ever was.
Remember the Javelins? Trump loves to bring this up. Obama sent blankets and MREs; Trump sent the anti-tank missiles that actually stopped the push toward Kyiv in the early days of the 2022 invasion.
There were also the massive sanctions on Russian oligarchs, the expulsion of diplomats, and the bombing of Russian-backed forces in Syria. In 2025, his administration even authorized the CIA to assist with strikes on Russia’s "shadow fleet" of oil tankers. That doesn't exactly scream "best friends forever."
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The Real Strategy: It’s Just Business
The most nuanced view is that Trump isn't "siding" with anyone but himself and his "America First" vision. He sees the world as a series of transactions.
Take the mineral deal.
There’s a massive agreement where the U.S. gets to extract rare minerals from Ukrainian soil in exchange for future military aid. Trump needs the war to end so the mining can start. If the war keeps going, Russia might take those resources, or they’ll just get blown up. To him, peace isn't about "justice" or "international law"—it’s about stabilizing the investment.
He’s also obsessed with the Arctic.
NATO Secretary General Mark Rutte actually credited Trump with waking Europe up to the fact that Russia and China are getting aggressive in the High North. Trump sees the sea lanes opening up and wants the U.S. to dominate the trade routes.
Why 2026 is the Breaking Point
We are at a weird crossroads. The New START treaty—the last big arms control deal between the U.S. and Russia—is about to expire in February. If Trump and Putin don't replace it, we’re back to a full-blown nuclear arms race. Trump already said he wants to start testing nuclear weapons again to stay "on an equal basis" with Putin.
Is that siding with Russia? Or is it just two guys with big egos playing chicken with the end of the world?
The NATO Divorce?
The biggest fear among European allies is that Trump will let Russia dominate Europe in exchange for a "hands-off" deal in the Western Hemisphere. It’s a "spheres of influence" model. "You take your backyard, I'll take mine."
But polling shows most Americans hate this idea. About 90% of people still think the U.S. has too many interests in Europe to just walk away. Trump is a populist; he follows the crowd as much as he leads it. If the American public stays pro-Ukraine, he might be forced to stay the course, even if his gut tells him to make a deal with Putin.
What This Means for You
Whether you think he’s a "Russian asset" or the "world’s greatest negotiator," the reality is that U.S. foreign policy has become totally unpredictable. This creates a few specific ripples you should watch for:
- Energy Prices: If a peace deal actually happens, Russian oil might flood back into the market, potentially dropping gas prices but also destabilizing the green energy transition.
- Defense Stocks: If the U.S. pulls back from NATO, European countries will have to spend hundreds of billions on their own militaries. That's a huge shift for global markets.
- The New Cold War: Regardless of the "friendship," the competition over the Arctic and rare earth minerals is only going to get more intense.
Next Steps for Staying Informed:
- Watch the "Shadow Fleet" Sanctions: If the Trump administration eases up on Russian oil tankers in the Mediterranean, it’s a huge sign that a "side-deal" has been struck.
- Monitor the February Nuclear Treaty: If the New START treaty expires with no replacement, expect a massive spike in defense spending and global tension.
- Check the Mineral Deal Progress: Follow news regarding U.S. mining companies in Ukraine. The moment ground is broken on those projects, you'll know exactly why the U.S. is pushing for a ceasefire.
The truth is, Trump isn't siding with Russia in the way a spy would. He’s siding with a worldview where the old rules don't matter, and everything—including a country’s borders—is up for negotiation.