Things were going so well for Mark Cuban—the Mavs won the title, his show Shark Tank has an audience, and he earned points putting his own money up to save the St. Patrick’s Day Parade in Dallas—that it was only a matter of time until he shot his mouth off.

That happened earlier this month at the MIT Sloan Sports Analytics Conference. Cuban, in a one-on-one conversation with Bill Simmons, ESPN‘s beloved Sports Guy, insinuated that Simmons is gay. Deadspin has the audio, but the short of it is that in the context of talking about ways to keep seat-holders’ attention off their cell phones and on the games, the discussion turned to the Mavericks’ Kiss Cam, which instigated the following:

Simmons: “Man, I really like the Kiss Cam.”

Cuban: “I know you do.”

Simmons: “The Kiss Cam plays great with my daughter.”

Cuban: “No, it’s cool. You and your boyfriend do it every day.”

Cuban knew right away he had screwed up. “Or his girlfriend,” he added. “This is gender-independent commentary.” But the damage was done.

Carly Carioli of the Boston Phoenix noted that Cuban was ribbing Simmons the whole conversation. “At one point, he sneered that he wished Simmons ran an NBA team,” Carioli wrote, “so that the Mavericks could crush them.”

Dan Devine of Yahoo, who seemed to feel badly for Cuban, wrote, “How big a bummer is it that this grown-ass man’s—this billionaire’s—idea of a killer joke was exactly the same as that of basically every middle-schooler in recorded history?”

Meanwhile,, a gay sports website, championed Cuban as an advocate for the LGBT community. The site only wished he had recognized the errors of his way earlier. “Of course, he waited until he got caught; He didn’t write this apology when it happened a week ago,” wrote Cyd Zeigler Jr. “Still, good for him. We would expect some sensitivity on this from Cuban. He is not an enemy of the gay community.”

For his part, Cuban addressed the issue on Blog Maverick. In the same breath as professing his love for fart jokes, he apologized for his “sophomoric” remark. He wrote that his own remark prompted memories of his childhood days as a bully.

I’m the last to be politically correct and the last thing I am trying to be here is politically correct. I honestly don’t give a shit what you think about me. But I think being the person I want to be includes not blurting out throw away jokes about sexuality, race, ethnicity, size, disability or other things people have no say in about themselves. I’m the guy who still feels bad about punching Michael Cooper in the stomach in 6th grade purely because he was overweight, even though I made the point to apologize to him when I ran into him at a reunion years later.

The entirety of Cuban’s post, though obliquely contrite, was pragmatic and well-intentioned. But a day later, Cuban tweeted:

And then, a day after that, Cuban tweeted again:

Doesn’t that sort of void his apology of sincerity?