Anyone who’s followed Colin Cowherd through the years knows he has some pet peeves, but arguably none greater than people wearing their hats backwards. This is a guy who last year dismissed JJ Redick’s potential as an NBA coach because of his backwards hat (“he looks like a guy who’s gonna move my couch). Cowherd proclaimed, “To turn your life around, you have to first turn your hat around.” Cowherd’s tough stance on hats earned ridicule from many, including LeBron James. ESPN’s Scott Van Pelt even took a subtle jab at Cowherd, showing video of Dallas Mavericks coach Jason Kidd wearing his hat backwards at a press conference, joking, “Oh, he’s got his hat on backward. That’s a problem for some folks in our business. Not for me, it’s fine.”
And Cowherd’s hatred for backwards hats dates back many years, raising the question: What drove Cowherd’s obsession with this issue? The Herd with Colin Cowherd’s YouTube page now features a highlight video showcasing the host’s many rants on hats being turned 180 degrees the wrong direction. In one memorable highlight from 2021, he revealed he’d studied the hat-wearing habits of every NFL quarterback, concluding the video with an explanation.
“Look at how good that hat looks,” Cowherd said, displaying the logo on a Miami Dolphins cap. “Unfortunately, when you lose a bet, this is all you see,” he continued, putting the cap on backwards (that must have been hard for him). “It’s a bummer. Let’s be honest, I look better this way, and more formidable as a sportscaster this way,” he said, turning the hat around. He then flipped the hat around the wrong way, adding, “This is cleaning out the garage guy. ‘Hey, how you doin’.”
“There’s a reason I don’t like hats on backwards, because I look so bad with a hat on backwards,” he confessed, providing insight into his long-standing proposition.
That’s not a great explanation of why Cowherd feels this way about hats pointing the wrong way. However, the fact he’s at least talking the issue out now shows he realizes he needs help.
