All the President's men

President Donald Trump's connection to the sports world was on full display on Monday.

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🎤 QUICK START ✍️

Screen grab: ‘The Dan Le Batard Show with Stugotz’

🐘 Dan Le Batard declines to address the elephant in the room. In what marked his first show since a Barrett Media report stating that Jon “Stugotz” Weiner would be ”stepping back” from his role at Meadowlark Media, Dan Le Batard declined to address the matter. The former ESPN host did, however, acknowledge the “elephant in the room” in the form of an inflatable elephant on the show’s set.

🏀 Prime Video adds UD Confirming previous reports, Amazon officially announced that it has added Dwyane Wade, Steve Nash and Candace Parker to its roster of NBA analysts on Monday. The streamer, however, also revealed that it will be employing former Miami Heat forward Udonis Haslem, who is currently working for ESPN.

🏈 Jon Gruden returns to pro football. More than three years after being fired by the Las Vegas Raiders after homophobic and misogynistic emails were leaked, Jon Gruden is back in professional football. Although it’s likely not as you imagined he would be, with the Super Bowl-winning head coach-turned-Barstool Sports personality joining Jeff Fisher’s ownership group with the Nashville Kats of the Arena Football One (AF1) league.

🚨LEADING OFF 🚨

Trump’s sports support

Screen grab: Associated Press

As news broke on Sunday night that President Donald Trump would be making a sports-related announcement the following day, many assumed it would involve an executive order connected to college football.

That, however, didn’t prove to be the case.

Rather, word quickly spread that the 45th and 47th president would help announce that Washington D.C. will host the 2027 NFL Draft. And that he did, standing right next to NFL commissioner Roger Goodell, Washington Commanders owner Josh Harris and D.C. Mayor Muriel Bowser as he made his announcement during a White House press conference on Monday afternoon.

So much for everyone just sticking to sports.

While the idea of the President of the United States standing alongside the NFL’s commissioner and a prominent team owner for a celebratory announcement might not have moved the needle even a decade ago, that isn’t the case now. After all, this is the same president who once referred to NFL players who knelt for the national anthem as “sons of bitches” and who has his own history with the league by way of his previous attempt to purchase the Buffalo Bills.

And yet, there Goodell was, awkwardly smiling and laughing along as Trump seemingly alluded to his belief that the 2020 election was rigged. And it was just last week that Philadelphia Eagles star running back Saquon Barkley felt compelled to take to X to defend his decision to play golf with Trump ahead of his team’s visit to the White House to celebrate its Super Bowl victory.

What does all of this mean? That likely depends on your own personal politics. But regardless of your opinion of Trump, it’s been impossible not to notice the way the sports world has embraced him during his second term.

From 2017-2020, teams merely going to the White House — if they were even invited — to celebrate championship seasons was viewed as controversial. And in addition to the kneeling NFL players, Trump also found himself publicly feuding with the likes of LeBron James and Stephen Curry at various stages of his first term.

Now? The only person in the sports world who Trump seems to be at odds with is one of his supporters in Dave Portnoy, in what would hardly qualify as a beef. Meanwhile, UFC pay-per-view events have effectively become Trump rallies, with the former star of The Apprentice often receiving his own mid-show introduction.

As a political figure, Trump remains plenty polarizing, especially with regard to deportations and the state of the economy. But he seems to have found a safe haven for support in the world of sports during his second term, with Goodell and Harris’ willingness to stand by him on Monday marking a stark contrast from what the scene likely would have looked like merely four years ago.

👀 AROUND AA📰 

Ahmed Fareed talks Derby duty

Just two days after filling in for Mike Tirico (peanut allergy) on short notice to anchor NBC’s Kentucky Derby coverage, Ahmed Fareed discussed his whirlwind weekend with Awful Announcing’s Drew Lerner. You can read the full Q&A here.

🎤 MEDIA MOMENTS ✍️ 

Credit: The Providence Journal

  • After agreeing to do an interview with Philadelphia’s ABC affiliate regarding the presence of a “F**k the Jews” sign at a Barstool-branded bar, Dave Portnoy said the local news station pulled a bait and switch on him. And the Barstool Sports founder even went as far as to post his own footage from the highly contentious interview, which showed him prematurely ending the conversation by slamming his laptop shut.

  • By this point, Kirk Herbstreit’s passion for his pets has been well established. And over the weekend, the College GameDay star added to his family, announcing the arrival of his golden retriever Peter’s half-brother, Beau.

  • You didn’t think we’d really go this whole newsletter without mentioning Bill Belichick and Jordon Hudson, did you? How could we ignore America’s sweethearts when Bill Simmons found a way to explain the demise of his beloved New England Patriots by using an email from Belichick that Hudson had leaked?

🔥 THE CLOSER 🔥 

Can TKO fix boxing?

Screen grab: DAZN

Lost in the shuffle of a busy NBA and NHL playoffs weekend was the news that TKO has announced its first boxing event: a Sept. 12 super fight between Canelo Alvarez and Terence Crawford at Allegiant Stadium in Las Vegas.

Ultimately, I’m not surprised the announcement didn’t move the needle, and not just because it was boxing’s “worst-kept secret” according to Sports Illustrated’s Chris Mannix. More so, it was because boxing is hardly a mainstream sport in 2025, with even the biggest fights possible barely registering to the average sports fan unless they involve Logan or Jake Paul.

That’s what TKO is looking to fix.

During an appearance on The Bill Simmons Podcast last month, WWE president Nick Khan discussed TKO’s vision of making its boxing promotion the sport’s version of WWE and UFC. That’s to say that it will be the dominant enterprise, the undisputed home of the top boxers — and champions — in the industry.

Doing that will obviously be easier said than done, especially considering the fragmented nature of the sport. But TKO has deep funding via Saudi Arabia and a clear vision that draws on its success in MMA and pro wrestling.

“It’s been proven with the UFC that people like to see a good fight,” Khan told Simmons. “They just have to know, as with the UFC, who the fighters are. It’s same with WWE. If you get invested in the fighters in UFC, which they’ve done a phenomenal job of doing, UFC has, if you get invested in the wrestlers in WWE, the more likely you tune in, the more likely you show up. It’s the same thing in boxing.”

The Alvarez-Crawford super fight is a strong start and it will be interesting to see how the promotion evolves from there. And it will especially be worth monitoring the media rights aspect of all of this, with Netflix already having been linked to the debut show, potentially providing TKO boxing the kind of exposure that could jumpstart this entire venture.

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