Former Obama speechwriter breaks down the gay-baiting questions he’s thrown at Pete Buttigieg

Secretary Pete Buttigieg
Secretary Pete Buttigieg Photo: Shutterstock

“Oh, God, that guy.”

That was Transportation Secretary Pete Buttigieg’s reaction to the news a former campaign aide would be joining Jon Lovett on his politico podcast Lovett or Leave It.

Former Mayor Pete has sat with Lovett for two interviews since joining the Biden Administration, both of which featured some unusual questioning from the comedian and former Obama speechwriter.

For the show’s pause and replay segment, “OK, stop,” Lis Smith, a senior advisor on Buttigieg’s presidential campaign, dropped by to break down the interviews and see where Lovett went wrong.

On the segment, Smith recounts how she’d seen Buttigieg the day before in Los Angeles at an event announcing new infrastructure spending and had shared the news she’d be auditing his two fraught interviews with Lovett.

“‘We are going to analyze his interviews with you,'” she told the former mayor, “‘and I stop and get to tell him when he really f*cked up, you know?’ And Pete’s like, ‘Wow, I didn’t know Jon had that sort of level of self-awareness to know how those interviews went. That gives me a new level of respect for him.'”

“I don’t know how many of you know Mayor Pete,” Smith explained to the audience, “but that’s like Pete’s Midwestern way, and like the Mayor Pete way of saying, ‘Bless his heart, and I hope he chokes in his sleep tonight.'”

Lovett then rolled tape on interview No. 1.

After Buttigieg explains strategies for distributing newly allocated funding for transportation infrastructure, Lovett deadpans, “You are saying it’s not the size of the infrastructure package, it’s how you use it.”

Buttigieg doesn’t blink, and continues explaining stakeholders and negotiating positions.

Smith then “OK, stops” the tape.

“I feel so much secondhand embarrassment for you right now,” she says to Lovett over audience laughter. Did Lovett ask any of his colleagues, “‘Hey, when I have an interview with a cabinet secretary, should I lead with a f*cking dick size joke?”

Lovett thinks he acquitted himself fine, and resumes the tape.

“I’m sorry, I’m offended,” Lovett says to Buttigieg. “I made a reference to a package. It is Pride. There was an innuendo there. And you ignored it.”

Buttigieg replies, “I tried to be oblivious.”

“Frank Kameny did not protest in front of the White House so that you can ignore my jokes during Pride, Secretary Pete.”

Lovett also rolled tape on a second interview, leading with a vaguely transportation-related question.

“Is Adam Driver hot?”

Smith stops the tape. “When you look at his face, you just see the disappointment. He’s like, God-f*cking damn. And I thought I was sitting down with Jon Favreau.” Favreau was widely considered to be the hot one of the Obama speechwriting duo.

Lovett hits play on a follow up question: “Chris Evans, Chris Pratt, Chris Pine or Chris Hemsworth?”

Buttigieg: “Chris Pine was in Star Trek, right? Oh, wait. Chris Pratt was in Parks and Recreation, right? Indiana connection, gotta go with him.”

Lovett: “Alright, for the record, he said he would f*ck Chris Pratt.”

Smith “OK, stops” again. “I think you’ve just got to ease in the questions a little more and maybe be like a little cliche, less cliched like about dick size, and which Chris he wants to f*ck.”

“Those are cliches interviewing a Secretary of Transportation?” Lovett asks defensively.  “I don’t think Norman Mineta got a lot of these questions,” referring to George W. Bush’s longtime (and straight) transportation secretary.

Smith suggested, “If I were asking questions of a cabinet secretary, and it’s like, ‘Who would you rather?’ I would ask about the other members of the cabinet,” she goaded. “I’m not saying you should.”

Lovett’s Crooked Media podcast Lovett or Leave It drops weekly.

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