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Ryan Dempster’s ‘Off The Mound’ show at the Innings Festival

The former Cubs pitcher is a funny and interesting talk show host.

Ryan Dempster with his Off The Mound guest Jim Thome
Al Yellon

TEMPE, Arizona — Former Cubs righthander Ryan Dempster started his post-playing career as a talk show host/joke-teller by just telling jokes among his teammates during long baseball seasons. He told me, “One of the things I loved most while I was playing was our clubhouse banter, our bus rides, plane rides. I miss playing, for sure, but I really miss the relationships, sitting around telling those stories.”

And that’s what got him started with his “Off The Mound” show, interviews and joking around with fellow ballplayers. You surely remember his interview with Kris Bryant at the 2019 Cubs Convention, where KB famously made this remark:

About that offhand comment about “St. Louis is boring,” Dempster said, “Yadi lost his mind about it, but that’s the worst thing Kris Bryant ever says. You just saw him at his low point, calling something boring, and I said, ‘Kris is boring! He never leaves his hotel room!’”

His focus on the show isn’t just talking baseball, either. Dempster told me, “You’re a baseball player way less than you’re not a baseball player. Sometimes I think we desensitize them as humans, and I’d like to bring a little bit of that back, represent who they are as people.”

Dempster will be bringing “Off The Mound” to the Marquee Network this season. The shows will be taped in front of a live studio audience, more of a late-night show format. About 100 people will be able to attend each taping — no, there are no details on how you’d get tickets to this yet — and there will be a different show each month. He’s hoping to possibly get David Ross on the show, or Theo Epstein, or maybe some celebrity Cubs fans like John Cusack or Bonnie Hunt or Eddie Vedder. Or, Dempster added, they might do some non-baseball things like having local musicians perform.

In addition, Dempster will be doing pre- and post-game work for Marquee, as well as some work in the booth during games. He said he’d either be “third man in the booth” or possibly occasionally substituting for JD if he has a day off. He’ll be doing pre-game and post-game for Opening Day and the home opener, and calling some games around the end of April. He also praised the network’s production values, saying “It’s national production values on a regional network.” Hopefully, everyone will be able to watch Marquee’s non-game programming soon.

I asked Ryan what he was doing in his Cubs special assistant role this year, and he said, “Mostly staying out of the way, if someone comes and asks me something I’ll try to help, but they already have great coaches here.” He did say he helped pitchers working on their bunting, something he was particularly proud of as a player, as he told me last year. “I feel if you can do all the little things in the game, don’t take those things for granted,” Dempster said, “then you give yourself a better chance to succeed.”

Regarding “Off The Mound,” Dempster says, “The guests are what make the show,” and he had some terrific guests in his Sunday evening show at the Innings Festival. Dempster first kicked things off by running a short video of him playing detective at Wrigley Field. Then he addressed those of you who don’t like his Harry Caray impression — by having someone who really does do a great Harry impression leave him a “voicemail” telling him to stop.

Hall of Famer Jim Thome was his first guest, and after a great interview Thome hit some baseballs into the crowd. Luis Gonzalez, perhaps the most popular player in Diamondbacks history, was the next guest and Dempster reminded Gonzo and the crowd that Luis had “lived every little boy’s dream, driving in the winning run in Game 7 of the World Series.”

Dempster finished up with his 2013 Red Sox World Series teammates Jonny Gomes and Mike Napoli. Much of that conversation was about beards. Napoli, of course, is now a Cubs coach, but Dempster made sure to credit those two with “getting me a World Series ring.”

The show was fun. Dempster’s a fun and funny guy and knows how to get ballplayers to open up not just about baseball but about life. The “Off The Mound” show on the Marquee Network should be a big success.

Here’s the entire Sunday evening “Off The Mound” show from the Innings Festival.

Many thanks to Bailey Wilson of Fresh and Clean Media and Lorraine Fisher of LDF Communications for their assistance.