Even Trump Can’t Stop Mocking Sean Hannity’s ‘Dumb’ Softball Questions

Donald Trump’s close relationship—on air and off—with Sean Hannity hasn’t stopped the president from mocking the Fox News star behind his back for being such a suck-up, according to three sources who have independently heard this mockery. These sources asked to remain anonymous in order to discuss private conversations with the president, and in one case also to avoid incurring the ire of Hannity, whom they called a “perfectly nice guy.”

Trump’s many radio and TV interviews, always touted as “exclusives” and rarely making any news, have been widely derided by media critics and political observers as simpering propaganda. And the president himself, a man famous for demanding relentless validation and unwavering loyalty, feels the same way.

Trump has repeatedly—and sometimes for a sustained period of time—made fun of Hannity’s interviewing skills, usually zeroing in on the low-quality laziness of the host’s questions, the three people with direct knowledge tell The Daily Beast.

“It’s like he’s not even trying,” Trump has said, one source recalled, right before the president launched into a rough imitation of Hannity’s voice and mannerisms to complain that the questions about how “great I am” give him nothing to work or have fun with.

Another person who’s heard Trump make similar comments since his inauguration says they remember the president calling Hannity’s softball questions “dumb.” This source recalled a round of ripping on the TV talker’s interview style and cloying devotion to Trump that lasted long enough that the source glanced at their watch and started feeling sorry for Hannity.

“Election Day [2016], I actually called you, I said, ‘You’re gonna get bad news about… 5:15 that afternoon. You lost Florida, North Carolina, Pennsylvania, Michigan, and Wisconsin.’ And you won ’em all. Polls don’t mean anything, do they?” Hannity asked during his most recent Fox News interview with Trump this month.

“I lost them based on the fake news,” Trump replied.

“Fake news,” Hannity repeated.

The president’s recurring complaints often focus on how sycophantic the TV host can be, both on and off camera, with Hannity’s slobbering leaving no friction to generate the sparks and drama that Trump craves.

“He likes it as sport,” a Republican close to the White House said, describing the president’s long-running addiction to sparring with media figures.

White House spokespeople did not respond to a request for comment on this story as of publication time. Neither did Hannity. Fox News declined to comment.

“[Trump] does enjoy the back-and-forth with the press—look at this whole Jim Acosta thing,” said Jeff Lord, a Trump ally and former CNN political commentator. “The president can call on anybody he wants. He could have ignored Jim Acosta. He didn’t do it. And he didn’t do it because… they would have some chance to do some verbal jousting there.”

Lord recalled that when he interviewed the then-future president at Trump Tower in 2014, Trump had enthusiastically promised he would “fight back” hard against the “dishonest” press if he ran for the White House. “Donald Trump delights in the combat with these folks,” Lord added.

Despite mocking Hannity’s softball questions, the president “loves Sean,” according to numerous Trump friends and White House officials, and is said to value him as a close pal and prominent informal political adviser who has his finger on the pulse of conservative America in a way few do.

“Sean [Hannity] told me last night…” is a phrase often heard by those closest to the president.

But Hannity is hardly the first friend or ally Trump has professed his love for even as he routinely disrespected or debased that person behind their back. For instance, when Oscar-winning actress and Trump acquaintance Marlee Matlin competed on Celebrity Apprentice, he repeatedly made fun of her by calling her “retarded”—simply because she was deaf.

With Hannity, Trump hasn’t always restrained himself until his friend was out of the room. Ahead of one of the president’s closing rallies before the midterm elections this month, the 2020 Trump campaign announced Hannity would be appearing onstage with Trump as a “special guest.”

Fox News began telling news outlets the “special guest” designation was wrong, and that Hannity would only be at the rally in Missouri to interview Trump for his show. Hannity himself tweeted the day of the event, “To be clear, I will not be on stage campaigning with the president,” and blamed any confusion on supposedly erroneous “reports” instead of Team Trump’s announcement.

In the middle of the political rally, the president called Hannity onstage anyway and told him to come up to the mic—which Hannity did to campaign with the president he supposedly just covers on air.

Hannity’s employer sprang into damage-control mode.

“Fox News does not condone any talent participating in campaign events,” the network said in a statement. “We have an extraordinary team of journalists helming our coverage tonight, and we are extremely proud of their work. This was an unfortunate distraction and has been addressed.”

According to a senior administration official, Trump was aware of Hannity and Fox News’ stated position that the host would not campaign that night. The president simply “did not care” and did it anyway, the official said.