Imagine you see former Cub Ryan Dempster leaving a restaurant in Chicago. He’s wearing the hard-to-miss World Series ring he won with the Boston Red Sox last year and, like so many people would, you want to take a photo with it. It feels like just about everyone in this city has a photo with the Stanley Cup trophy, but a picture with a World Series ring? You’ll be the envy of your Facebook friends. And isn’t that why you take these sorts of pictures? The valet hands Dempster the keys to what is most likely an impressive car (there’s a reason the semi-retired Dempster was able to walk away from the $13.25 million he would have made pitching for the Red Sox this season), and now you need to make a decision. You’re not sure you’ll have this opportunity again.
Do you approach Dempster?
In this case, you can. Dempster says so.
“I enjoy sharing it with people,” Dempster said Saturday at “Toast the Champ for 22q” — a Dempster Family Foundation fundraiser held at Howells & Hood to raise awareness for 22q deletion syndrome. “It’s a great, special thing for me. I want them to get a feel for what it’s like and what it looks like. I don’t wear the ring every day, but I wear it a lot, like when I go out to a nice dinner.”
Dempster, 37, played 16 seasons in the Major Leagues, nearly nine of which were with the Cubs. The father of three announced in February he would take the year off to spend more time with his family and focus on his health. Dempster’s daughter Riley was diagnosed with 22q two days after she was born; it affected her speaking and breathing and led him to get involved with the cause. Now he gets to spend the time with Riley — and his other children, Brady and Finley — that he wasn’t able to while playing baseball, whether it’s wearing tiaras during dress-up time or unintentionally learning the words to “Let it Go” from Disney’s “Frozen.”
“(You learn) just how fast kids grow up,” Dempster said of his time away from the game. “When you’re playing baseball you’re gone for a week, and when you’re home, you’re busy the whole time. I got to chase my goals for a long time and now I get to watch my kids chase theirs.”
Besides spending times with his kids, the two-time All-Star has been traveling (he just got back from a relaxing hiking and whitewater rafting trip in Montana and is planning to visit Scotland next) and appearing on MLB Network as a studio analyst for a few days each month.
“When you get the camera in front of you, you feel like you can say you know it all because you played it,” Dempster said about his MLB Network gig. “But you have to stay humble and remind yourself how hard the game is to play. I approach it that way. My mentality has always been positive. I’m not the type to rip a guy. (Players) say I’m doing a good job. I don’t know if they’re blowing smoke up my dress.”
Dempster said he occasionally misses the camaraderie in the locker room. But other than that, he’s at peace with his decision. And while he hasn’t closed the door on his career, he said he hasn’t had the itch to return either.
“Fortunately, I haven’t missed it,” Dempster said. “Not yet. With the way things ended with the World Series, I don’t feel like I’m missing it. Hopefully I don’t ever get that feeling.”
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