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Sara’s Diary, Day 43 without baseball: An interview with Ryan Dempster

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the former Cubs pitcher gave me a behind the scenes look at his Friday night talk show “Off the Mound”

Ryan Dempster hosts Off the Mound at the 2020 Cubs Convention

Yesterday the Governor of Illinois extended the state’s stay at home order to May 30 and as the COVID-19 pandemic stretches on one of the things I’ve noticed is that it can be hard to tell one day from the next. However, for the next few weeks Cubs fans will want to set a reminder on Friday evenings at 7 p.m. CT to be sure they tune into Marquee Sports Network for a six-episode run of Ryan Dempster’s late night talk show “Off the Mound” presented by Sloan. The former Cubs pitcher was kind enough to chat with me for a few minutes earlier this week about what he’s been up to during the pandemic and what fans can expect from the show.

The first episode of “Off the Mound” debuted last week with Mike Trout and Anthony Rizzo. In case you missed it, Dempster shared some clips. My favorite moment hands down was Dempster teaching soon-to-be father Mike Trout how to put a diaper on a stuffed rabbit:

It will shock no one that Mike Trout is apparently also a natural at diapering stuffed animals, but it might surprise you that Dempster has been developing and writing “Off the Mound” since before the show first debuted at Cubs Convention in 2015.

Dempster always had a reputation as clubhouse entertainer during his playing days. But it’s a lot more than just his famous Harry Caray impersonation. After he retired from pitching, he took classes at ImprovOlympic in Chicago in the hopes of following in the footsteps of his late-night idol Johnny Carson — you know, but with baseball. He’s taken the show live, too: Here’s a review Al wrote about Dempster’s “Off The Mound” show at the Innings Festival in Tempe, Arizona last month.

While Dempster gets a bit of help with the development of the show from the writers at Marquee Sports Network now, he’s still pretty hands-on with the material. For the Trout piece he worked with Mike’s wife Jessica to make sure all of the props were in place. Trout was completely surprised at the scene. Dempster described teaching Trout how a diaper works as “passing on veteran leadership.” He also sagely advised the three-time MVP that whenever Jessica needs him to change a diaper, the answer is always yes.

The debut show also included a conversation with Anthony Rizzo about the work the Rizzo Family Foundation has been doing to provide meals to hospital workers during the pandemic. That project helps feed workers on the frontlines of the health care system while also boosting the restaurant industry, which has been hit particularly hard by the economic shutdown. Dempster has been personally involved in supporting that effort and will continue highlighting charitable work with each episode of “Off the Mound”:

Like all of us, Dempster and his wife wanted to be able to give back. He said when looking around to see ways to have a big impact he knew he could trust Rizzo’s foundation. It was touching to hear Dempster express the same awe all of us have experienced with Rizzo’s never ending commitment to charitable work. As Dempster put it, it’s easy to write a check but: “Anthony also gives his time, knowledge and partnership.” He also really emphasized the intention behind Rizzo’s project to provide meals saying, “It’s not just the meal, sure the nourishment is nice, but it’s the feeling you give them to let them know you care about them and appreciate the work they do.”

It was abundantly clear to this daughter of an emergency room nurse that Dempster has been thoughtful about paying it forward during this trying time and that he and his wife are investing in ways to show our essential workers gratitude for the work they are doing to keep us safe. I appreciate that he’s using his platform to highlight that work so others can join.

Tonight’s show airs at 7 p.m. CT on Marquee Sports Network and will feature conversations with his former teammates Derrek Lee and Greg Maddux. Lee and Dempster played together for 12 seasons between their time with the Marlins and Cubs. Here’s a preview from tonight’s show:

Both are outstanding storytellers and I imagine a dozen seasons provides more than enough material without too much talk about 2003. Maddux and Dempster were only on the same roster for about two years, but Ryan indicated they have a great time poking fun at John Smoltz, which is something I definitely want to see.

I appreciate Ryan making the time to give me a behind-the-scenes look at “Off the Mound” for the readers of BCB and I am looking forward to taking my mind off the pandemic with some great baseball stories later tonight.