The two world leaders will meet Friday in Alaska, the precise location yet to be announced. How soon will Trump know if the Russian president really wants to end the fight in Ukraine?
"Probably the first two minutes, I'll know exactly whether or not a deal can be made," Trump told reporters Monday.
Ukraine President Volodymyr Zelenskyy has balked at the idea of giving up any amount of land. Ukrainians will not "gift" their land or reward Russia for its actions, he has said, noting that his country's constitution defines its territorial integrity and that "no one will deviate from this – and no one will be able to."
There's optimism in the Trump camp going in. "If there's anybody who can confront and deal with and manage Putin, it's Donald Trump," State Department spokesperson Tammy Bruce said Sunday on Fox News' Media Buzz.
But that's far from a universal opinion. Media coverage from The Financial Times, Le Monde and Bloomberg say it could be Putin who plays Trump.
"One thing that's impossible to ignore is that whenever Trump threatens sanctions against Moscow, he finds a way to avoid following through. Remember the 50-day deadline? And then the 10-day deadline?" Fox News columnist Howard Kurtz writes.
Rep. Pat Harrigan, a North Carolina Republican, said on Washington Watch Monday that the media coverage isn't far off the mark.
"I tend to believe that it is not in Russia's best interest to end this conflict. I think the purposes for which they are fighting are not really well understood by the West – and I think because of that, it's very likely that this is a delay or stall tactic," Harrigan, a former Green Beret, told show host Jody Hice.
The gap in understanding may come from different cultures focusing on different histories.
The way Russia sees things
The West tends to look at the Ukraine conflict through a post-World War II lens that sees borders as sacred; they must be respected.
Many in Russia, meanwhile, remember Ukraine as part of the former Soviet Union. Ukraine didn't declare its independence until August of 1991 during the Soviet Union's collapse. Parts of Ukraine had been ruled by Russia before the Soviet Union.
Now Moscow promotes the idea that Ukraine is historically and culturally inseparable from Russia – a belief rooted in imperial and Soviet-era propaganda. This narrative downplays Ukraine's distinct history and sovereignty, framing the war as a "reunification" rather than an invasion.
Even while Putin is evasive and hard to read, the U.S. must take advantage of the opportunity for a face-to-face meeting at a somewhat central location "on the off chance that we might get something out of this," Harrigan said.
"It is absolutely in the best interest of the United States of America for this conflict to end. We need full-throated support for President Trump and his endeavors to end this conflict," he added.
Russia does not want the conflict to end. In fact, Harrigan says, every drone launch by Putin is an attack on the U.S. economy. It's a common goal for a Russia-China partnership, says the GOP lawmaker.
"Every day that they fire $50,000 drones and elicit a million-dollar American-missile response is a day that we lose the economics of war. Russia and Xi (China President Xi Jinping) working together pushes the United States closer and closer to a fiscal cliff that nobody knows exactly where it is, but they know which direction it is in," Harrigan said.
The economic approach could be a case of turnabout as fair play.
"I'm very concerned that Russia and China are working together to effectuate effectively the financial takedown of the United States, much the exact same thing that Ronald Reagan worked against the Soviet Union 30-plus years ago," Harrigan said. "We need to be cognizant of the fact that might be going on right now."
The U.S. has authorized the transfer of longer-range Army Tactical Missile System (ATACMS) missiles to Ukraine, allowing Kyiv to use them for deep strikes inside Russian territory, particularly in the Kursk region.
These missiles have a range of approximately 190 miles (300 kilometers) and are capable of hitting military targets such as airfields, ammunition depots, and troop assembly areas.
The Biden administration authorized this use in late 2024, partly in response to Russia's reported deployment of North Korean troops.
The cost of doing business
Such precise weaponry is expensive, as Harrigan explained.
"We have become very dependent on highly capable, but very exquisite, very expensive military end items. When we provide those items to our allies, the 50 different nations that purchase military equipment from us, yes, they become very capable. But if that war goes on for a protracted period of time, they also start losing the economics of war right alongside of us," Harrigan said.
The war certainly needs to end because of the high cost of life, but if it continues with no end in sight the U.S. will need to look for the most cost-effective ways to assist while working toward strategic goals. The high cost of material is a real consideration.
"We've got to be cognizant that we may, based on the technology, end up hanging a financial millstone around their necks, just as we're hanging a financial millstone around our own necks. I think that Russia is very knowledgeable of this fact," Harrigan concluded.
