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August 20, 2025

Can Donald Trump Grin Down the Russian Bear?

His summit with Vladimir Putin in Anchorage, Alaska gave the self-proclaimed master artisan of dealmaking a chance to prove his own legend.

By Joshua Arnold

This past weekend, President Donald Trump attempted to pull off his own stunt, one which only the legendary Davy Crockett had ever successfully performed — and only in the legends — grinning down a bear. Fortunately for him, Trump’s target is only a metaphorical bear — the 72-year-old former KGB agent who now rules post-Soviet Russia with an iron grip. And the contest is only a metaphorical grin-off — securing a ceasefire in Ukraine. So, while the 79-year-old Trump is no Fess Parker, his summit with Vladimir Putin in Anchorage, Alaska gave the self-proclaimed master artisan of dealmaking a chance to prove his own legend.

Russian Demands

Of course, grizzly-grinning is neither easy nor safe, or else everyone would do it. The bear brings his own personality, weapons, and — in this case — his own list of demands to the sport. Putin wants an end to Western sanctions against Russia but less access for Ukraine. He wants the West to formally recognize Russian control over Crimea, a Ukrainian province Russia illegally seized in 2014. Russia wants Ukraine to reinstate the Russian Orthodox Church and recognize Russian as an official language — to satisfy an ethno-cultural-nationalism theory eerily reminiscent of 1930s Germany.

Most challenging of all, Putin wants the Ukrainian people to “demilitarize” and accept a disastrous “land swap.” In the trade, Russia would exchange 155 square miles of unimportant terrain it holds in northeastern Ukraine for 2,550 square miles of strategically critical territory in southeastern Ukraine (the Donbas region).

Russian-aligned forces have held parts of the Donbas — a highly populated, industrialized area of Ukraine — since its 2014 invasion, so the Ukrainians have had plenty of time to develop the rest of the territory into a defensive frontier known as the “fortress belt,” which has held back Russian offensives for more than three years. Putin wants Ukraine to surrender this fortified frontier without firing a shot, which would leave the rest of Ukraine undefended against any future Russian invasion.

Putin’s ploy — a powerful aggressor demanding that a smaller neighbor voluntarily surrender its most defensible frontier — is similar to that used by Adolf Hitler to secure the Sudetenland in 1938. Both leaders justified their land grab along ethno-nationalist lines. Soon after Czechoslovakia lost the Sudetenland, German armies overwhelmed the entire nation. Whether Putin would honor a peace deal with Ukraine once it lost all means of successful resistance — that is, whether a bear would spare a captured salmon — remains to be seen. (Russia already violated treaties when it invaded Ukraine, and it is currently in violation of a nuclear arms agreement with the U.S.).

In exchange, Putin was willing to accept Western guarantees for Ukraine’s future security. The West made guarantees in 1994 to coax Ukraine into returning Soviet-era nuclear weapons to Moscow. Those guarantees have now failed to deter two successive Russian invasions.

Mixed-Bag Results

What unfolded between principals during this First Frontier Face-off? The results were decidedly mixed. The Russian grizzly was by no means “grinned down.” On the other hand, neither did he eat Trump — not even a single finger or toe.

Amid a torrent of unreasonable Russian demands, Trump failed to cement the ceasefire he has pressured both sides to accept for months. The two leaders parted amicably but abruptly, canceling a working lunch and declining to take questions from reporters. Trump’s entourage left Anchorage so quickly that they left behind documents on a hotel printer.

Given the lack of progress, the cordial greeting for Putin — including a literal red carpet — struck some observers as overly effusive. The meeting helped Russia escape its bear’s den of diplomatic isolation, without any concrete concessions to show for the effort. Putin has also apparently evaded Trump’s threat to impose “very severe consequences” if Putin failed to agree to a ceasefire at the summit. However, as the president has demonstrated with Iran and other nations, his tolerance for unfruitful negotiations is not endless.

Yet forcing Russia into a ceasefire was always a remote possibility. One could just as easily argue that Trump’s greatest success in Anchorage was not agreeing to a bad deal. This was no small feat, given Putin’s remarkable ability to charm and hoodwink American presidents at personal meetings over the years.

“Putin [is] hoping to dazzle President Trump. He’s hoping to delay. He’s hoping to maybe create a wedge issue between the United States and Ukraine or the United States and Europe, and all of those things are in his repertoire,” argued Brig. General (Ret.) John Teichert on “Washington Watch.” “But I think President Trump is very clear-eyed in his desire to see that ceasefire or a commitment for follow-[up] negotiations. And, anything short of that, he will see through President Putin as just a delay tactic in his negotiation plan of bad faith.”

In fact, Trump was reportedly “ready to walk away” over Putin’s insistence on acquiring Ukraine’s fortress belt. “If Donetsk is the thing here and if there is no give, we should just not prolong this,” he reportedly said.

“As a tactical matter on the ground for the United States of America, what really matters is to make clear the aggression, [the] killing of civilians that’s happened all across Ukraine — they’ve now taken 20,000 Ukrainian kids and taken them into Russia, taken them away from their families — as a Christian, it’s just absolutely abhorrent. We have to make clear that this kind of aggression is not rewarded. It cannot be seen as a Vladimir Putin victory,” declared former Secretary of State Mike Pompeo on “This Week on Capitol Hill.” “If it is seen that Vladimir Putin took this land by aggression, and the West conceded it, it will embolden our adversaries all across the world.”

In recognition of the difficult task before them, the White House set modest goals for the Anchorage summit. “The president has been very clear that he is not there to negotiate,” Teichert told listeners. “He is there to set conditions so that there can be a follow-[up] meeting that includes President Zelensky, so that Russia and Ukraine can negotiate together.”

“While Putin may try to push him on accepting concessions,” he continued, Trump was “thus far showing that he is in his home field advantage with the position of strength, is not going to get pushed around by Putin, is going to insist either on that ceasefire or the commitment for follow-on negotiations that include Ukraine.” In fact, Trump greeted his grizzly guest with a bang, as the U.S. Air Force executed a five-plane flyover before Putin even left the tarmac.

American Leadership

In fact, whatever the outcome and future ramifications of the Anchorage summit, Trump has unmistakably asserted American dominance, making himself the channel through which all other diplomacy runs. Whereas Trump formerly met Putin in Helsinki, Finland, this time, Putin traveled to American soil. Trump then relayed the results from this meeting to Ukrainian President Volodymyr Zelensky, as well as America’s European allies. Afterward, both Zelensky and European heads of state quickly arranged to travel to Washington, where they met Monday afternoon to discuss their next steps.

Trump may not have grinned down a bear in his first meeting, but he is the only one who went into the den and came out unscathed, and now everyone wants to hear his story.

“In a lot of ways, Putin’s already lost this war, in that we added two new members to NATO, Finland and Sweden, and we have seen a consolidation of European strength and a commitment to raise their defense spending now to that 5% threshold,” Teichert reflected. “All of those have come partly because President Trump has encouraged them to do that, but also because they’ve seen that the world is a dangerous place with people like Putin, Xi, and others.” Trump has orchestrated for himself a position of strength. And, by aiming for grand, difficult objectives, he stands to make his position even stronger, barring a spectacular failure.

No man can live up to his legend, but the existence of the legend can inspire him to heroic feats, even to grinning down the icy Russian bear.

Joshua Arnold is a senior writer at The Washington Stand.

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