His post-playing days are just as enviable.
He frequently has appeared on MLB Network as a color analyst, serves as a special advisor with the Cubs, and hosts Off the Mound with Ryan Dempster. For the second straight year, he will be bringing the talk show to Innings Festival, where he'll interview featuring a star-studded lineup of Hall of Famers and Diamondbacks legends like Luis Gonzalez and Mark Grace over four segments.
Phoenix New Times caught up with Dempster to talk about his favorite spring training restaurants, the power that comes with being an athlete, and what fans can expect at Innings Festival.
Phoenix New Times: You’re back in Arizona during spring training. What’s your favorite memory?
Ryan Dempster: Baseball players are almost like a Navy SEALs squad. We do a mission, and then we disappear for five months. Then [spring training] is about getting reacclimated with your teammates and developing those relationships again. It’s like getting the band back together for another go-around: the dinners, the laughs, and the excitement for the long season. You hear, “I’m in the best shape of my life” from every guy.
Do you remember any of your favorite places to eat or hang out spots from your springs spent in Arizona?
The Mastro's circuit [Mastro’s Steakhouse, Mastro’s Ocean Club, and Mastro’s City Hall] is always nice. You always find the guy who has the biggest paycheck that season and make sure to invite him. Just bumming around Old Town and those places there to get a nice cold beer. Dinner at the Mission is always nice, too.
You've worn a lot of different hats since retiring. What drives you to stay so close to baseball after all these years?
I love the game. To be in it in different aspects is a lot of fun. To be a part of the Chicago Cubs and the organization and watch the World Series and be a part of it as a front office guy was really cool.
Were you there the night they finally won it?
I was. I didn’t miss a playoff game. Being around those guys was special. It was like I was on the 60-day DL with no chance of a rehab assignment. They treated me like one of the players, and it was special to watch them go out there and do what so many people were trying to do for 108 years.
You were on the 2013 Red Sox World Series champion team and pitched in Game 1. How often are you sitting around and just think, "Damn, I pitched in the World Series?"
You pinch yourself sometimes. The last hitter I ever faced was a punch out to end a game in the World Series. You want to talk about a cool special feeling, and then to win it all and go out on top like that? It’s a special bond. I could not see someone for five years and then run into them and it’s like no time has passed, especially that year with everything going on and the [Boston Marathon] bombing. It was a pretty special year.
My father lives in Maine, which is part of Red Sox Nation. I was up there that summer and just to see what the team did for the community was so special.
It was a give and take. We were given this incredible honor and privilege to help this city come back from this devastation, but at the same time, the city gave us that power. We wanted to make Fenway a part of the healing process.
You’ve also given a lot to the community since retiring. This past summer, you held a benefit for the Special Olympics
We’re nothing as baseball players without our fans, and some of our fans need some extra help and support. To do that benefit for Special Olympics Illinois and to hang with the athletes was so special. I did this event called Coaster Karaoke with Tim Hanlon, who is a Special Olympic weight lifter. We were singing on the Goliath roller coaster at Six Flags. After the third time doing it, the saxophone player had to get off because he was going to throw up. Tim just looked at me and said, “Well Ryan, I guess roller coasters aren’t for everybody.”
That event was tied into your Off the Mound with Ryan Dempster. What drew you to want to do this program?
I feel like we detach from athletes and celebrities in a way where we forget that they're still people. I wanted people to see what they do in their communities and how they give back. We want to humanize the athlete. With fantasy sports, we dislike a player because he went 0-4. We forget that sometimes you win, and sometimes you lose.
It’s so easy for fans to dehumanize athletes now. I’ll be at games and fans are swearing up and down at a player.
And I don’t know how or why it got that way. You used to have to do something pretty awful, but now you just have to have a bad week. Next thing you know, fans let other fans know you’re the worst. That’s a son, father, or brother out there. Let’s lighten up a bit.
You have this ability to connect with fans though. What can they expect from you at Innings Festival?
Our show is fun and lighthearted. We have a great line-up of ex-MLB players and some current players. We’ll share some laughs and music. Look at Jake Peavy: He’s a Cy Young winner who opened up for Willie Nelson at a concert a couple of months ago. It’s to celebrate all sides of a player.
Who can we expect at the festival?
We have Rick Sutcliffe and Mark Grace together. That’s like Abbott and Costello. They’ll be zinging each other back and forth. We’ll have Kevin Millar, who is always a hoot and has stories for days. We’ll have Luis Gonzalez. Years and years ago, I went to Japan on an All-Star tour over there. At 2:30 in the morning, I went into a bar, and Luis Gonzalez was singing “La Bamba.” I can’t wait to bring that up with him.