Dan Le Batard & Pablo Torre Credit: Pablo Torre Finds Out

Dan Le Batard became linked during his time at ESPN to former president Donald Trump. Le Batard’s frequent bashing of Trump, how he would often call out ESPN’s policies around political commentary, and his refusal to publicly stand up to Trump as a company led him to really stand out. But in the debut episode of a new show on Le Batard’s own network at Meadowlark Media, he reckoned with his own decisions to make content out of Trump’s persona in three ESPN Radio interviews from 2013-2015.

“I haven’t felt in a long time the way that I feel right now where I’m listening to something back that we have done, and I’m genuinely afraid of what it is that happens next and how it is that it’s going to embarrass me because in retrospect it becomes very clear how foolish we were,” Le Batard said of the softball questions lobbed Trump’s way and the unserious tone of the segments.

The comments come from Pablo Torre Finds Out, the new Meadowlark production airing on YouTube and the DraftKings Network. Torre played clips of Trump for laughs before turning the conversation over to a more serious reckoning with Le Batard’s choices and line of questioning.

Le Batard and cohost Jon “Stugotz” Weiner booked Trump when he was still hosting The Apprentice. Not when he made cable news appearances amid his unfounded questioning of Barack Obama’s birthplace for any actual political aims. They asked about him everything from Adrian Peterson to Trump’s golf game to the parties and yachts he had access to in the rich guy circles of Manhattan and West Palm Beach.

Le Batard seems to feel real shame in hindsight:

“I don’t think there’s anything in my life, never mind the history of American politics as I viewed it, that has left me feeling more foolish than underestimating what total shamelessness could do to American systems that I thought were stronger than that.

“I would have never guessed that I would be so stupid as to think that from that entity could come the challenging of the principles that we hold dearest allegedly as a country.”

In particular, Torre (who was sitting in as a guest host for the third and final Trump interview in the spring of 2015) and Le Batard discuss their own mistake in treating Trump with kid gloves. That despite questionable business dealings and the racist undertones of the “birtherism” conspiracy around Obama even in the mid-2010s.

“I had no idea from that perspective of my view of America that that conversation would be seen as something dangerous instead of playful because I’m arming somebody casually with the ability to say ‘no, I don’t regret that I was claiming that Obama had a fake birth certificate,’ Le Batard said.

“I’m guessing you could find my voice on something saying that I was hoping that Donald Trump would run for president, not because I thought that he would win in any conceivable, fathomable idea, but because I wanted the circus of anarchy that would come with him debating legitimate politicians.”

Dating back to 2016 and the Access Hollywood locker room talk” tape and on through Trump’s xenophobic comments toward Congresswoman Ilhan Omar, Le Batard locked horns with Trump from afar and consistently sparred with ESPN management over his leeway to do so.

Of course, it would be foolish to believe that how ESPN Radio hosts handled Trump truly affected his political career. But for Le Batard, who went out of his way to take on Trump from within the walls of Disney at a time when few were, it clearly stands out as a regret.

“The naivete in it is a bit stupefying,” he said.

Torre expanded the conversation to end the episode by wondering what could be learned from Le Batard’s extended history with Trump, first as a show guest and then as a running villain.

“I did not know I could be this big of a fool showing my ass in front of this many people. But if your starting point on all of that is being able to make fun of yourself because you were a fool and you tried to do a vaguely principled thing at ESPN by leaving to create your own thing,” Le Batard said, “I was telling people in the creation of this company, ‘I feel like these microphones are going to matter, the independence of these microphones is going to matter … we need to have the freedom of the microphones in 2024 so we can learn from our mistakes and so that we can do it better.'”

Since leaving ESPN, Le Batard has frequently held political conversations on-air and interviewed guests about the social and political issues of the day. It remains to be seen how aggressively Le Batard will cover the 2024 presidential cycle, though the fact that Florida Gov. Ron DeSantis is campaigning places the news right in the Miami-based Le Batard’s backyard.

[Pablo Torre Finds Out on YouTube]

About Brendon Kleen

Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.