'Real Time' guest tells Bill Maher Trump was 'intimidating' at summit, Putin looked like his 'caddy'

Trump ally Walter Kirn told Bill Maher that the POTUS was in control and that Vladimir Putin looked more like his 'caddy' than a strongman
UPDATED AUG 17, 2025
Bill Maher discussed Donald Trump and Vladimir Putin's Alaska summit with his guests on the August 15 episode of 'Real Time' (Getty Images, HBO)
Bill Maher discussed Donald Trump and Vladimir Putin's Alaska summit with his guests on the August 15 episode of 'Real Time' (Getty Images, HBO)

ANCHORAGE, ALASKA: When Donald Trump met Vladimir Putin in Alaska, some pundits said the US president got “steamrolled.” But author and Trump ally Walter Kirn wasn’t buying it.

Kirn told Bill Maher that Trump was the one in control and that the Russian leader looked more like his “caddy” than a strongman.

US President Donald Trump (R) and Russian President Vladimir Putin (L) meet during a US-Russia summit on Ukraine at Joint Base Elmendorf-Richardson in Anchorage, Alaska, on August 15, 2025. (Photo by ANDREW CABALLERO-REYNOLDS / AFP) (Photo by ANDREW CABALLERO-REYNOLDS/AFP via Getty Images)
US President Donald Trump and Russian President Vladimir Putin (L) meet during a US-Russia summit on Ukraine at Joint Base Elmendorf-Richardson in Anchorage, Alaska, on August 15, 2025 (ANDREW CABALLERO-REYNOLDS/AFP via Getty Images)

The comments came during the Friday, August 15 episode of 'Real Time with Bill Maher' on HBO, where Kirn sparred with Maher and fellow panelist Molly Jong-Fast over the optics of Trump’s high-stakes sit-down with Putin in Anchorage.

Bill Maher sets the stage for discussion on Alaska summit

The episode’s featured guest was Atlantic staff writer Thomas Chatterton Williams, promoting his book 'Summer of Our Discontent: The Age of Certainty and the Demise of Discourse'. The panel included Kirn, a best-selling author and editor-at-large of County Highway, and Jong-Fast, host of 'Fast Politics' and author of 'How to Lose Your Mother: A Daughter’s Memoir'.

Maher opened the floor by joking about his own Alaskan memories. “I went to Alaska in 2013. I think I had a better trip. I at least did a show. Surprising, disappointed, what’s your reaction?” he began.

Kirn quipped, “I wish it had happened in winter because the only outfit I haven’t seen Trump wear is a parka. I mean, McDonald’s uniform, a garbage truck driver, I also wish there had been more outdoor activities, it being Alaska, they could have gone fishing, but the world is divided between people who didn’t want it to happen and people who don’t want to succeed."

U.S. President Donald Trump and Russian President Vladimir Putin meet for their summit on the war in Ukraine, at U.S. Air Base on August 15, 2025, in Anchorage, Alaska, United States. Putin is having a one-day trip to Alaska. (Photo by Contributor/Getty Images)
US President Donald Trump and Russian President Vladimir Putin meet for their summit on the war in Ukraine at the US Air Base on August 15, 2025, in Anchorage, Alaska (Contributor/Getty Images)

"You seem to want it to succeed, so do I. Unless we’re going to get rid of Putin, unless we’re gonna eliminate him, we could have dropped a bomb from that B-2. We’re gonna have to talk to him at some point," he added.

Maher was skeptical. “Who doesn’t want it to succeed? Everybody wants it to,” he said. 

“There are people who didn’t want to see Putin walk across that red carpet and didn’t like it when Trump waved to him," Kirn responded, as quoted by Mediaite.

Walter Kirn felt Putin looked like Trump's 'caddy'

Molly Jong-Fast argued the optics weren’t exactly normal. “I mean, it crushed some norms having him walk across a red carpet while Trump clapped. I mean, that generally… Oh, come on. Putin doesn’t get…” she said.

But Maher rolled his eyes. “Oh, come on, are we really going to go through this kind of bulls**t like Obama wore a tan suit and he’s saluted with coffee in his hand? Who gives a s**t what he’s walking through? I mean, there’s people dying over there,” he said. 

That’s when Kirn dropped his “caddy” line.

“The body language, to me, put the lie to the notion that we’ve had for 10 years that Trump is Putin’s stooge," he said. "Putin looked like his caddy. I mean, he really did. He’s half his height. He was sort of smiling uncomfortably. I think we can lay to rest the idea that Trump was some Russian agent. I actually wish that he’d been a little kinder to him. I thought he was intimidating.”

ANCHORAGE, ALASKA - AUGUST 15:U.S. President Donald Trump (R) and Russian President Vladimir Putin (L) hold a meeting at Joint Base Elmendorf-Richardson on August 15, 2025 in Anchorage, Alaska. The two leaders are meeting for peace talks aimed at ending the war in Ukraine. (Photo by Andrew Harnik/Getty Images)
US President Donald Trump and Russian President Vladimir Putin hold a meeting at Joint Base Elmendorf-Richardson on August 15, 2025, in Anchorage, Alaska. (Photo by Andrew Harnik/Getty Images)

Trump’s Ukraine gambit

Walter Kirn’s defense of Donald Trump came just as The New York Times dropped a bombshell report about what the POTUS told European leaders after his meeting with Vladimir Putin.

According to two senior European officials, Trump backed a plan to end the war in Ukraine by giving Russia territory it hasn’t even conquered yet, something that has apparently left European allies and Kyiv furious.

The report claims Trump will pitch the plan directly to Ukrainian President Volodymyr Zelensky at the White House on Monday, with some chatter about other European leaders joining.

(L-R) U.S. President Donald Trump greets Ukrainian President Volodymyr Zelensky as he arrives at the White House on February 28, 2025 in Washington, DC. Trump and Zelensky are meeting today to sign a preliminary agreement on sharing Ukraine’s mineral resources that Trump says will allow America to recoup aid provided to Kyiv while supporting Ukraine’s economy. (Photo by Chip Somodevilla/Getty Images)
US President Donald Trump greets Ukrainian President Volodymyr Zelensky as he arrives at the White House on February 28, 2025, in Washington, DC (Chip Somodevilla/Getty Images)

Officials reportedly told The New York Times that Trump dropped his demand for an immediate cease-fire. He believes a rapid peace treaty is possible if Zelensky agrees to hand over the rest of the Donbas region, including parts not currently under Russian control.

In return, Putin supposedly offered a cease-fire at the current battle lines and a written promise not to attack Ukraine or Europe again.

Needless to say, Ukraine isn’t having it. Zelensky and European leaders have blasted the idea of ceding unoccupied, mineral-rich land that also doubles as key defensive territory. The European officials stressed to The Times that “it will be up to Ukraine to make decisions on its territory” and reiterated that international borders “must not be changed by force.”

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