Like any kid growing up, Ryan Dempster had an idol.
You’d figure that an aspiring baseball player would worship major-leaguers. But that wasn’t the case for a young Dempster. Growing up in Gibsons, British Columbia, his adoration went to Johnny Carson.
Dempster would stay up late to watch “The Tonight Show.” Just how late was he allowed to stay up?
“I don’t want to rat out my dad,” said Dempster, now 43. “I was pretty young.”
Dempster liked falling asleep happy after hearing a joke or an amusing story or watching an entertaining skit. He even had his favorite guests.
“I was always hoping that it would be Burt Reynolds again,” he said, “because every time he went on it was hilarious.”
Dempster has carried that happy feeling with him ever since, through a 16-year major-league career that included nine seasons (2004-12) with the Cubs to a second career as a broadcaster on the Cubs’ Marquee Sports Network, where he has been able to combine two of his passions: talking baseball and entertaining people.
Dempster initially was going to be part of a rotation of additional game analysts, but Cubs fans have seen much more of him than expected. Dempster has filled in for Jim Deshaies, who was out with a knee injury, and has been called upon more because he lives near Wrigley Field.
“Many of our [personnel] decisions are now based, obviously, on COVID-related factors,” Marquee general manager Mike McCarthy said. “Ryan is local and can make more appearances than anyone needing to travel, and he has made more appearances than others in part for that reason.
“That said, Ryan is a budding star, and Marquee and its viewers have enjoyed his work this season and expect much more from Ryan in the coming seasons.”
Dempster isn’t a finished product in the booth, but his pitching demonstrations are insightful, and like booth mates Len Kasper and Jim Deshaies, he’s an easy, comfortable listen. He said he tries to bring more to his analysis than the knowledge he has gleaned since he was a third-round pick by the Rangers in 1995.
“I’m trying to bring the actual emotion of what it’s like to be a big-league ballplayer,” he said. “Let’s understand that there are humans out there, and there’s a guy 60 feet, 6 inches away, and he’s also required to win. I can relate to that.”
He’s also trying to bring humor.
“Anybody who knows me knows I love the stage,” Dempster said. “I like entertaining. I want people to have a good time.”
He took that to another level in June 2001 with the Marlins on the night before a start against the Red Sox in Boston. He was at the Comedy Connection at Faneuil Hall with his father, Wally, and teammates Mike Lowell and John Mabry when he had an urge to perform.
“I wasn’t drinking, and I got up there,” he said. “I wasn’t very funny.”
With more time on his hands after baseball, Dempster has taken up improv-comedy classes, and he has performed at the Comedy Bar on Superior Street.
“I’ll try anything,” he said. “I can go up there and totally bomb, which I have done, and it sucks. It takes a lot of work. I’m not naïve. I know how hard all these guys have worked to do anything like this.”
Dempster keeps working at it, but unlike his classmates, he has his own show to put his lessons to work. “Off the Mound with Ryan Dempster” debuted in 2018 at the Vic Theatre in the vein of a late-night talk show. It debuted on TV in February with the launch of Marquee. As much as Dempster enjoys hosting, he wants his guests to take center stage.
“I want to bring the best out in my guests and get them to relax,” said Dempster, who has hosted such baseball luminaries as Mike Trout and Ken Griffey Jr. “I have to be the one to facilitate that, to give them that space and be able to share stories and feel comfortable doing that.”
The show was put on pause so the network could dedicate its resources to live game coverage during the pandemic, though it has continued in podcast form. McCarthy expects new TV episodes in the near future.
In the meantime, Dempster will remain a part of Cubs broadcasts, where he’s a natural fit. He became a fan favorite by excelling first as a closer and then as a starter, and he has immersed himself in not just the Cubs’ culture, but Chicago’s.
“Playing here for a long time and caring about the team and the city, I’m forever grateful for Chicago,” Dempster said.
