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Trump Says He’ll Know in ‘First Two Minutes’ If Ukraine Deal With Putin Is Possible

US President Donald Trump is setting the stage for a high-stakes meeting with Russian leader Vladimir Putin, saying he’ll size up the chances for peace in Ukraine almost instantly — and isn’t ruling out walking away.

A Meeting With the Weight of a War on Its Shoulders

Donald Trump has always loved the idea of quick reads on people. And now he’s applying that same gut-level instinct to one of the most brutal wars in modern Europe. Speaking to reporters in the White House briefing room on Monday, the president said his upcoming summit with Putin in Alaska will be a “feel-out” session — but one that could pivot the war’s direction in minutes.

“I’ll know exactly whether or not a deal can be made in the first two minutes,” Trump declared, flanked by Defense Secretary Pete Hegseth and Attorney General Pam Bondi. His tone was casual, but the stakes couldn’t be higher.

The meeting is scheduled for Friday in Anchorage. It comes as Washington faces not only the task of brokering a ceasefire but also the political optics of sitting down with a leader whose February 2022 invasion of Ukraine has left tens of thousands dead and millions displaced.

Why Alaska, and Why Now

The choice of Alaska isn’t accidental. It’s US soil but geographically closer to Russia than any other state, offering a symbolic halfway point without the pomp of European capitals.

Some insiders say Trump pushed for the location to frame the meeting as distinctly American territory — a reminder that, despite hosting Putin, he’s not playing on Moscow’s turf. Others see it as a quieter setting where both leaders can test each other without the swarm of European press conferences.

Donald Trump Vladimir Putin Alaska

One notable absence will be Ukrainian President Volodymyr Zelensky. The White House floated the idea of inviting him, but aides now acknowledge it’s “unlikely” he’ll attend. That leaves a symbolic hole in the discussions, since any potential ceasefire deal will need Kyiv’s buy-in.

Trump’s “Might Be Good, Might Be Bad” Gambit

If Trump’s blunt rhetoric is a negotiating tactic, it’s classic him. “It’ll be good, but it might be bad,” he told reporters, painting two stark scenarios: one where he wishes Putin “lots of luck” and another where they shake hands on a deal.

This isn’t new for Trump. Back in his real estate days, he relished making quick judgments in boardrooms. The difference now is that instead of skyscraper contracts, the subject is territory, sovereignty, and lives.

For Moscow, the goal is clear — cement gains made since 2022, including territory Russia still occupies in eastern Ukraine. For Washington, the calculus is murkier. Any deal that’s too generous to Russia risks alienating NATO allies and triggering backlash at home.

Washington Police Takeover Announcement Overshadows Briefing

Interestingly, Trump didn’t call Monday’s press conference to talk foreign policy at all. The official reason was his plan for a federal takeover of Washington, D.C.’s police force, citing crime concerns.

Yet, the Ukraine question quickly overshadowed the crime announcement. By the time the briefing ended, headlines weren’t about policing at all — they were about whether peace talks could hinge on Trump’s gut feeling in a two-minute window.

  • Trump’s domestic pitch: Tough on crime in the capital.

  • The global takeaway: High-risk, high-reward diplomacy with Putin.

Risks for Both Leaders

From Putin’s perspective, this meeting offers a chance to appear reasonable without conceding too much. It also lets him engage directly with Trump without the filter of European intermediaries.

From Trump’s side, the optics are trickier. He’s trying to portray himself as the dealmaker-in-chief, but any public perception of being soft on Russia could haunt him politically. History hasn’t been kind to US leaders who misread Moscow’s intentions.

In 1986, Ronald Reagan famously walked out of talks in Reykjavik when Mikhail Gorbachev’s proposals clashed with US interests. Some see Trump’s “two-minute” comment as laying the groundwork for his own walkout moment if things sour.

The Ukraine Factor Without Ukraine in the Room

Not having Zelensky present is both a diplomatic gap and a political signal. It spares Trump from the potential awkwardness of a three-way meeting where Ukraine’s leader directly challenges any concessions to Russia. But it also risks sidelining the very nation the talks are supposed to help.

A State Department official, speaking on background, put it bluntly: “Any agreement made without Ukraine’s active participation will be hard to enforce and harder to sell internationally.”

The Two-Minute Test — Can It Really Work?

There’s a reason seasoned diplomats cringe at the idea of sizing up peace prospects in a matter of minutes. Wars, especially ones as entrenched as Ukraine’s, rarely hinge on first impressions.

Still, there’s an argument that Trump’s approach could break through the usual scripted talking points. The theory is that leaders reveal their true intentions quickly in face-to-face encounters. Whether that’s enough to bridge the chasm between Russia’s demands and Ukraine’s sovereignty is another matter.

Table: Key Issues Likely on the Table in Alaska

Issue US Position Russian Position Likely Middle Ground?
Ceasefire terms Withdrawal from occupied areas Recognition of Russian control over some territories Localized ceasefire lines
NATO expansion Freeze eastward expansion Formal pledge from US/NATO Security assurances without treaty changes
Sanctions Gradual easing if compliance verified Full lifting Partial rollbacks tied to monitoring
Prisoner swaps Immediate release of POWs Exchange only if sanctions lifted Phased swaps

What Comes Next

After Alaska, the pressure will mount quickly. If talks fail, the war’s momentum will likely continue into another winter, with both sides digging in. If there’s even a partial breakthrough, Trump could claim a rare diplomatic win that few thought possible.

But first, those two minutes.

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