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Gerry Callahan is Out at WEEI After 20 Years

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The major shakeup going on at WEEI just went to a 9.9 on the Richter Scale.

It’s hard to believe that just a few short months ago, Kirk & Callahan were the No. 1 rated morning show in New England. After years of the station getting its ass handed to it on morning drive by Toucher & Rich, Minihane and Callahan had righted the ship, caught up and passed them. Then Kirk was forced out by the station caving to pressure from outside sources that he’s way more qualified to talk about than me, so I’ll leave that to him. The ratings plummeted. And the rumors that have been out there about Callahan being next turn out to be true. His contract was up in August. It’s been reported that he wouldn’t get renewed. But they didn’t let him get to the end of his deal.

You’d think 20 years of helping to carry WEEI and putting millions into the pockets of the station, the sales people and the ones making the decisions, management would’ve earned him at least leave on his own terms. To give him a final week and a graceful send off. But they went with disgraceful. Just pack your shit and go. Such is the nature of the business, I guess. At least it’s the nature of the company I worked at for two years.

Gerry Callahan is a controversial, polarizing radio voice, there’s no disputing that. And I won’t for a hot second pretend to be neutral because I’ve always been a fan. He was one of the very first media stars in the market to embrace Barstool. In our infancy, he and John Dennis read verbatim, with full credit, a post I’d written celebrating the death of the supremely evil Jack Tatum, one of early “We’ve made it” moments in my Stool career. Dennis & Callahan had me on a few times. They had Dave Portnoy on regularly and stood by him after HowitzerGate, fighting with management to keep him on the air when virtually the rest of the on-air staff was screaming he should be locked up. And when I became a semi-regular fill in around 2014, Dennis, Callahan and Kirk were all lobbying for upper management to make me full time. And I’ve never once seen Callahan in person when he didn’t ask about my family. So yeah, I’m not objective. It’s personal.

I’ve even forgiven him for the time we were at the White House for the 2016 Patriots visit and Mr. Kraft was yelling to “Jerry” from the balcony and Callahan just assumed he was saying “Gerry” when we all knew it was me he was talking to. Because I’m just that kind of gracious, magnanimous guy.

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But what’s not personal is that he’s as smart a person as I’ve ever heard on radio. He’s always been an unapologetic right-wing conservative, but you don’t have to agree with his politics or embrace his worldview to concede how talented he is at backing up his arguments. I’d say the same thing if he was a moderate, progressive or a libertarian. He’s one of those guys you meet that makes you feel like they’ve got like 28 hours to their day to the 24 the rest of us get and he spends those extra four hours learning shit to bring up at a later time. Of course in 20 years he’s said some dumb, regrettable shit that he’d love to have back. Welcome to the world of speaking extemporaneously into a hot mic for 20 hours a week with millions of people listening. That said, controversial, polarizing, smart and well-informed? You’d assume that would be the perfect formula for a morning talk show host in a major media market like Boston. Not in 2019, it would appear.

To be honest, I’ve kind of felt bad for Callahan since Kirk left. He’s been carrying a rotating list of lesser co-hosts like Jordan with the 1987 Bulls. And on the rare occasion I’ve listened, it’s been sort of painful. 20 years is an eternity in that business and I have no doubt he’ll end up doing something more suitable to his talents. In the meantime, I’ve talked to a few of the guys who used to work at EEI and it saddens us to see the once thriving cultural institution we left doing so badly. It’s like being safely on the Carpathia wrapped in a dry blanket drinking hot coffee and watching the unsinkable ship you got off us sinking under the North Atlantic. I won’t speak for Callahan, but I bet someday soon he’ll realize they just put him on a lifeboat.