Barack Obama’s decade-long relationship with retiring Daily Show host Jon Stewart can fairly be described as a friendly one. During his final interview with Stewart earlier this month, the president joked that he would be issuing an executive order preventing Stewart from leaving the job. The pair has been described as a couple in a romantic comedy and in more searing terms by right-wing critics like Sean Hannity.
On Tuesday, Politico disclosed new details about just how important Obama viewed his relationship with Stewart, reporting that the president summoned the Comedy Central performer to the White House on multiple occasions to make the case for his policies, including one occasion where he laid out his re-election pitch.
Jon Stewart slipped unnoticed into the White House in the midst of the October 2011 budget fight, summoned to an Oval Office coffee with President Barack Obama that he jokingly told his escort felt like being called into the principal’s office.
In February 2014, Obama again requested Stewart make the trip from Manhattan to the White House, this time for a mid-morning visit hours before the president would go before television cameras to warn Russia that “there will be costs” if it made any further military intervention in Ukraine.
In the 2011 meeting, just less than a year before he would face re-election, Obama used the occasion to set the groundwork for his 2012 campaign and respond to liberal critics, according to former top economic aide Austan Goolsbee.
“The White House itself was quite interested in at least explaining its side of the story to Jon Stewart,” Goolsbee told Politico, “up to and including the president.”
Politico also describes how Stewart’s show could sometimes influence White House thinking, including on policy issues.
In March 2009, Stewart discussed the new Obama administration’s idea of removing veterans with private insurance plans from the VA rolls. “That can’t be right,” he intoned. The Obama White House scrapped the plan one day after his segment aired, and veterans’ advocates recall Stewart’s commentary being discussed during a West Wing meeting with senior aides including then-Chief of Staff Rahm Emanuel.
“I can’t say that because Jon Stewart was unhappy policy changed. But I can say that he had forceful arguments, they were arguments that we knew would be heard and deserved to be answered,” former senior Obama adviser David Axelrod said.
Axelrod, who was on the show the night that Stewart announced his retirement and has been a regular guest, told Politico that he kept in touch with Stewart by phone and email during his time in the White House.
While Stewart occasionally goes after Democrats, the GOP has clearly been his most frequent target over the years. Sen. Claire McCaskill said that her party is taking his imminent departure seriously. “I’ll tell you some Democrats are worried,” she told Politico.
Obama was the first sitting president to appear on The Daily Show, making his fifth appearance on the show just days before the 2010 midterm election. “The president hasn’t been shy about going to the places where people are getting their information and trying to make his case,” then-White House press secretary Robert Gibbs said at the time.
"Few people in media had the ability to influence the political debate like Jon Stewart," longtime Obama advisor Dan Pfeiffer told Politico earlier this year when Stewart announced his retirement. He added that Stewart “conducted some of the toughest and most insightful interviews of the president.”
Former White House press secretary Jay Carney called Obama’s 2012 pre-election interview with Stewart the “toughest” he faced during that campaign. “[It was] probably the most substantive, challenging interview Barack Obama had in the election year,” he told CBS News Chief White House Correspondent Major Garrett last year.
If the White House actually viewed him as a “challenging” questioner, they also apparently viewed him as someone who would be receptive to specific pitches from the president. From Politico:
In Stewart’s first show after his February 2014 visit to the White House, he picked up on the Russia-Ukraine news that Obama had spoken about in the press briefing room a few hours after their private chat.
Calling out excessive military bellicosity is one of Stewart’s strong suits, so the Obama meeting certainly didn't necessairly have to have had an influence for him to do a segment like that. It is notable, though, that Stewart went specifically after critics of the White House’s response to the Russian invasion as being overly hawkish, including Sen. John McCain.
“I don’t think that there’s any doubt that with his 'comedy' that he had an effect on the workings of government,” McCain told Politico.