KC radio host Carrington Harrison on Jason Whitlock: ‘The fork in the road was clearly that Deadspin article.’

One of the more surprising changes over time from a prominent sports media figure came with Jason Whitlock.

Whitlock’s prominence largely came from sports coverage, in print, online, and on TV and radio. But the last few years have seen him become much more of a conservative political pundit. That’s perhaps especially true with Whitlock’s current media role, hosting Fearless with Jason Whitlock for Glenn Beck’s Blaze Media.

Kansas City radio host Carrington Harrison, the latest guest on The Awful Announcing Podcast, told host Brandon Contes this week that Whitlock has made a clear political pivot. Harrison ties that to Greg Howard’s 2015 Deadspin article “How Jason Whitlock Is Poisoning ESPN’s Black Grantland.”

First, some Whitlock background. He started his career in newspapers, working at The Herald-Times in Bloomington, Indiana, The Charlotte Observer, and The Ann Arbor News before joining The Kansas City Star in 1994, where he worked through 2010. He gained national prominence as a sports figure from his Star work and his work for ESPN (2002-06, 2013-15), AOL Sports/FanHouse (2006-07), and Fox Sports (2007-13, 2015-20), and also did radio work for Kansas City stations WHB and KCSP.

But Whitlock’s second tenure at Fox saw him start to dive into conservative politics much more intensely than he had before. That was part of an overall amplification of takes from him, but his most notable takes brought in more politics than he had previously been known for. That even included a sketch mocking Colin Kaepernick that FS1 ultimately declined to air.

Whitlock’s post-Fox stops at Outkick (2020–21) and Blaze Media (2021-present) have seen even more emphasis on politics. And they’ve seen some fiery takes in that realm, such as videos asking if Michelle Obama is transgender and criticizing women having the vote. And Whitlock has continued to weigh in on sports figures as well, doing so in a way that’s even drawn remarkable pushback from the likes of Stephen A. Smith.

Harrison, host of The Drive on KCSP 610 Sports AM in Kansas City, has an interesting perspective on Whitlock. He grew up in the Kansas City area reading Whitlock in The Kansas City Star. Harrison then followed Whitlock through his career there and on the national stage, even interviewing him on the radio once.

As part of a larger conversation with Contes on this week’s AA podcast, Harrison discussed his history with Whitlock. There, he brought up how he thinks that the 2015 Deadspin article on the failures of Whitlock’s The Undefeated project at ESPN (which would eventually be launched in 2016 under Kevin Merida following Whitlock’s exit and is now Andscape) and its fallout altered Whitlock’s path.

To start with, Harrison tells Contes he grew up admiring Whitlock, and he compares Whitlock’s pivot to famous wrestling moves from one affiliation to another.

“Man, Whitlock was my hero when I was a kid. Just Black, opinionated, wrote for the Star, and this was when the Star was the paper. You look back for all the people that used to work at The Kansas City Star, like Jeff Passan and Wright Thompson and Whitlock and Joe Posnanski, just a foundation of your sports fandom. So to see him cross over to like, NWO, that’s kind of what I equate it to.”

He also says he finds it hard to equate Whitlock’s current stances with what he heard from him in the past.

“I got to interview Whitlock one time. He came in studio and came on the show and I told him he was somebody I looked up to. I remember I asked him about Ferguson and Darren Wilson, and the answer he gave then would be a completely different position than he’d give now about the situation.

“So I don’t know, man. That saying about meeting your heroes and seeing how magic works…it’s kind of crazy how my fandom of Whitlock has just changed over the years, but that’s life, I guess.”

Harrison attributes that change to how things went with that Deadspin article (and its remarkable revelations on Whitlock’s time trying to launch The Undefeated) and what happened afterward. That included Whitlock pushing back publicly, then exiting the project (which was launched in a very different fashion the next year, under The Undefeated, and then leaving ESPN (where he was not doing a lot after that exit) to return to Fox.

“I think there’s always like a fork in the road, like most of us in our career,” Harrison said. “I think the fork in the road was clearly that Deadspin article. And, you know, this was during a time where Grantland was, if you were in sports media, you loved Grantland.

“And Grantland’s evolved into The Ringer, obviously a very successful website and podcast network. But this was when Whitlock tried to make Grantland, and obviously that failed. And then you’ve got the behind-the-scenes look.”

Harrison said Whitlock’s recent stances perhaps make sense given the places he’s landed.

“I think Whitlock was sort of looking for a home and someone that would accept him. The Black folks wouldn’t accept him anymore, so he had to find a home. And he’s definitely crossed over to a completely different team.”

Harrison doesn’t have a lot of personal experience with Whitlock. But the one time he did meet him face-to-face started promising but turned disappointing. And part of that was about Whitlock not only asking for an expensive barbecue order as a prerequisite to being interviewed but then refusing to talk ahead of time.

“Funny story, we have a close mutual friend, and there’s a barbecue restaurant that we both like called Gates. And they were like, ‘Hey, Whitlock will do it, but here’s his food order.’ And I’m kind of broke at the time, and I’m like ‘I get to get Jason Whitlock some food, I’ll do it.’

“So he sends me the order and I didn’t really have a good understanding of how much it was, so I go to Gates, and it’s like a $52 order, and I’m like ‘All right, I’ve never spent that much money on somebody that I wasn’t going to eat any of the food, but all right, cool, whatever.’

“So I get there, and we kind of have a little area just to our own, and I’m not going to lie, I kind of fanboyed out for a minute: I had a plate for him, and a setup for him, and a napkin. I was really excited that Jason Whitlock was here, you know? I was really excited.

“So Whitlock comes up there and I have his food. And I’m like ‘I want to go say something to him,’ but I’m trying to play it cool. But then I’m like ‘Man, I paid all this money for the food, I’m going over there.’

“And I go over there and I’m like ‘Hey, big fan, I’m happy that you’re here.’ And he’s like ‘All right, I’ll talk to you later.’ And I was like ‘What?! Hold on, that was it?’ So yeah, that’s my one Jason Whitlock story the one time I got to meet him. I wanted him to be a little friendlier to me.”

Harrison’s full appearance on The AA Podcast can be found here. Subscribe to the show on Apple Podcasts, Spotify, and wherever you get your podcasts. For more content, subscribe to AA’s YouTube page.