Colin Cowherd: ‘When is [Caitlin Clark] going to start winning?’

The excitement of Caitlin Clark being the WNBA’s fun, shiny new toy is over, according to Colin Cowherd. Now it’s time to start winning.

Cowherd and Tyrone Johnson agree the grace period is over for Caitlin Clark. Where they disagree, however, is that Johnson compared Clark to Jeremy Lin, or a one-hit wonder. Whereas Cowherd believes Clark’s career is at the point where it should take off, like Michael Jordan or Taylor Swift.

Clark was a rookie sensation, and she was injured for most of her second season. But in year three, Cowherd believes now is when the pressure to win should start to set in for Clark. Similarly, Jordan was a rookie sensation; he was injured for most of his second season, and in his third year, he averaged 37 points per game. Jordan also led the Chicago Bulls to a below .500 record in his third season, but Cowherd ignored that part for the sake of this argument.

“When is she gonna start winning at the next level? She has not won a playoff series yet. My take is, she has her Pippen, Kelsey Mitchell…

“This is not hating on Caitlin Clark, but the stage of ‘Wow, who’s the new kid?’ I’m done with that.” – Colin Cowherd on Caitlin Clark pic.twitter.com/wg9VsTL383

— Awful Announcing (@awfulannouncing) May 18, 2026

“When is she gonna start winning at the next level? She has not won a playoff series yet. My take is, she has her Pippen, Kelsey Mitchell,” Cowherd said. “This is not hating on Caitlin Clark, but the stage of ‘Wow, who’s the new kid?’ I’m done with that. That was awesome. That was Taylor Swift’s self-titled album…and then it was ‘Fearless,’ which crushed her self-titled album. I need ‘Fearless.’”

The question is, why now? What happens if Clark doesn’t start winning championships until her seventh season, like Jordan did? It will have no bearing on her legacy. Yet Cowherd is speaking as if Clark has already blown opportunities at winning a championship, when she really hasn’t had any. Clark went to the playoffs her rookie season, and she was injured in year two, when Indiana won a series without her.

“Has she won a playoff game?” Cowherd asked. “No, she hasn’t even won a playoff game, forget a series…this team should vie for the championship if she is what I think she is.”

Which is apparently some super hybrid of Michael Jordan and Taylor Swift. But what professional basketball player was given championship-or-bust expectations after playing just one full season? Jordan didn’t have those expectations, nor did LeBron James. And Caitlin Clark doesn’t really have them either, despite Cowherd’s attempt at claiming she needs to win now.