Let's unpack that statement a bit.
First, according to White House chronicler in chief Mark Knoller, Obama appeared on "The Daily Show" twice as president -- Oct. 27, 2010, and Oct. 18, 2012. You can read the 2010 transcript here and the 2012 one here. (Per the photo above, Obama also sat down with Stewart as a candidate for president on Aug. 22, 2007.)
In the 2010 interview, the "toughest" Stewart gets is when Obama notes that the host had been critical of a certain timidity when it came to the Affordable Care Act. "I don't mean to lump you in with other presidents," Stewart told Obama. "But I think if I were to try to coalesce whatever criticism of it may be, it's that you ran on the idea that this system needed basic reform." The overall tone of the interview, however, was decidedly friendly.
Ditto the 2012 interview. Again, Stewart poked Obama on his poor performance in the first presidential debate that year -- "What happened? What -- did you feel -- did you -- here's what happens to me sometimes, sometimes I'll go on stage and I'll have let's say an open-faced turkey sandwich and a shot of NyQuil?" -- but, in general, the comedian's questions were well within the bounds of normal, and the president, as any good politician does, wound each one back to a talking point he wanted to emphasize.
There's an important distinction between Stewart and most of the rest of the people who get to interview Obama; Stewart interviewing Obama is not the same thing as, say, WaPo's Scott Wilson interviewing him. (Scott was the last Post reporter to get time with Obama -- back in 2009!) I'm not going to get into the debate of who is a journalist and who is not -- it's counterproductive and pointless in this day and age of reporting -- but it is indisputable that Obama (and his team) approach a sit-down with Stewart very differently than they would with The Washington Post or the New York Times.
Obama will naturally be more playful with Stewart than with, say, Peter Baker of the Times. And, while Stewart largely stuck to serious topics during both of his interviews, he is given leeway -- by both the president and the show's viewers -- to have fun and go off topic. Such diversions by a White House correspondent for the Times or Post would be roundly castigated -- not only by the public but, sadly, by many of his or her colleagues, too. There's a "stay in your lane" mentality that governs mainstream media interviews with the president that someone like Stewart simply doesn't have to contend with.
So, there's that. But there's another reason, too, why the idea of Stewart as Obama's toughest questioner rings false.
And that's that venues like "The Daily Show" are actually getting time with Obama. Despite a standing request for an interview, The Post hasn't had time with Obama in more than five years. I reached out to Baker at the Times who told me that the last time a White House correspondent for that organization interviewed the president was in July 2013, when Mike Shear and Jackie Calmes talked to him about economic policy. Since then, Obama got on the phone with Jason Horowitz for a profile of his longtime White House travel director Marvin Nicholson. (Obama also chatted with Times columnist Tom Friedman.)
This is not meant to read as a complaint from a whiny reporter who thinks his outlet doesn't get enough love from the White House. Instead, it's a statement of fact. Obama has given Jon Stewart more of his time than he has The Washington Post or even the New York Times during his presidency.
Remember, too, that this White House is extremely savvy in its media strategy. Recent sit-downs with Vox, a left-leaning policy site run by former Postie Ezra Klein, and BuzzFeed, the premier site of the social web, are examples of how the Obama administration carefully uses the available media outlets to best sell its preferred message or messages. And Obamaworld has never been terribly shy about critiquing the mainstream media as a tail-chasing ghost of its former self.
Pfeiffer's comment about Stewart fits nicely into that worldview. And he may well be right about some of the less-appealing tendencies of mainstream media. But what he's not right about is that Jon Stewart was somehow the questioner of President Obama that the mainstream media never could be. We never really got the chance.