When Donald Trump meets Vladimir Putin in Alaska on Friday, most predict a loyal lieutenant and adept foreign policy expert will be by his side.
On regulated exchange and prediction market site Kalshi, 92% of users predicted Secretary of State Marco Rubio would be there with Trump when he sits across from the Russian authoritarian leader at Joint Base Elmendorf-Richardson in Anchorage, Alaska, in a bold attempt to end the bloody war in Ukraine.
But coming in a close second is Trump’s special envoy to the Middle East, Steve Witkoff, who is deemed to be an 87% chance.
Witkoff, who has known Trump since the 1980s and plays golf with him, has earned the nickname the ‘Putin whisperer’ because he’s met with the Russian leader four times since January.
After Wikoff, Vice President JD Vance is third at 64%.
However, it’s the fourth choice that could be awkward if it proves correct.
And if there’s one trait Americans know about Trump, it’s he likes to surprise with an outsider.
Sitting just above even odds as a 53% chance is rising cabinet star and secretary of the treasury, Scott Bessant.
More than $227,000 in bets have been placed on who will accompany Trump to the meeting.
Unlike the others in the market, Bessent, 63, has been extremely critical of the Russian president in the past.
In May, the former hedge fund manager gave a speech to the House Committee on Financial Services where he was asked for his thoughts on Putin.
Democratic Rep. Juan Vargas asked the Treasury secretary: ‘Do you consider Vladimir Putin a war criminal?’
Bessent responded with a simple but direct answer: ‘Yes.’
Vargas then asked Bessent, ‘Would you negotiate with a war criminal?’
He replied: ‘I think that’s the nature of diplomacy, one must negotiate with both sides, sir.’
Friday’s upcoming summit, which will not include Ukrainian President Volodymyr Zelensky, is the most significant diplomatic event between the US and Russia since the start of the war in 2022.
Putin convened a meeting with Kremlin officials on Thursday where he praised Trump by stating he believed the president was making ‘quite energetic and sincere efforts’ toward peace in the region.
The Russian leader suggested long-term peace could be reached if the US included strategic offensive weapons treaties in the upcoming negotiations.



