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

Dan Le Batard has long prided himself on being the voice of Miami.

But when it comes to the Portland Trail Blazers trading Damian Lillard to the Milwaukee Bucks — and not Miami — the Meadowlark Media co-founder is truly on Heat Island.

Four days after the blockbuster trade that sent Lillard to Milwaukee, the Trail Blazers made another move, trading All-Star point guard Jrue Holiday — who was acquired in the Lillard deal — to the Boston Celtics. But while many praised Portland for the totality of the haul it received for its now-former franchise player, Le Batard took another route, accusing the Trail Blazers of being “wonderfully petty.”

“You have to admit that Portland not wanting to deal with Miami at all is one kind of funny,” Le Batard wrote on the social media platform X, “but actively hellbent on trading specifically to make Miami’s chief opponents in the East better is wonderfully petty.”

While it’s unclear whether Portland actually refused to deal with Miami regarding Holiday, it’s worth noting that Le Batard has strong sources in the Heat’s front office. At one point, that placed him at the center of the summer-long Lillard sweepstakes, as he served as the Heat’s (literal) mouthpiece during the public negotiations.

“Thank you for bringing up [Adrian Wojnarowski]…the Heat know that he’s just agenda-based, shilling, bought and paid for by Portland. It’s embarrassing that Woj is telling people it might be weeks or months on Lillard,” Le Batard said on The Dan Le Batard Show with Stugotz on July 17.

But after Lillard was traded to Milwaukee more than two full months after those comments, many threw them back in Le Batard’s face — including The Ringer’s Ryen Russillo. Le Batard, for his part, called the criticism of him “fair” and reiterated that he was sharing the Heat’s point of view more than his own.

Thus, some may have assumed that it’s also the Heat’s viewpoint that Portland was being petty in not only refusing to trade Lillard and Holiday to Miami, but also trading both players to Eastern Conference contenders. That, of course, seems like a massive stretch. So it shouldn’t be ruled out that Le Batard is simply making a tongue-in-cheek observation about the circumstances of the Trail Blazers’ trades.

But while the motive behind his post might be unclear, what is certain is that when it comes to the Heat — and in particular, team president Pat Riley — Le Batard is willing to give the franchise the benefit of the doubt. The former Miami Herald columnist said as much on Friday as he pushed back against criticism of the team’s front office.

“I want Lillard. I want them to get all of the great players for my content factory,” Le Batard said during his show. “I also trust [the Heat] to properly assign value to the things in their organization better than I can do it. It doesn’t mean they get it right all the time. It doesn’t mean that they don’t make mistakes.

“You guys have seen what Pat Riley’s done with his team through very many rosters. He’s clearly pretty good at what he does. You want to criticize him on these things and think you know more than him? OK. I would’ve preferred to have Lillard. I would have given plenty to get Lillard. But at what point do you trust an organization to assign proper value to its business better than you can do it?”

It’s fascinating to hear someone who has built a sports media empire as a columnist and sports talk radio host essentially push back on one of the staples of the industry. But Le Batard has never been one to embrace debate. And if nothing else, he’s aware of his biases when it comes to all things Miami — and in particular, the Heat.

[Dan Le Batard on X]

About Ben Axelrod

Ben Axelrod is a veteran of the sports media landscape, having most recently worked for NBC's Cleveland affiliate, WKYC. Prior to his time in Cleveland, he covered Ohio State football and the Big Ten for outlets including Cox Media Group, Bleacher Report, Scout and Rivals.