A Long Conversation With Ryan Dempster About Things On and Off the Mound

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Ryan Dempster spent 16 years in the Major Leagues, more than half of them in Chicago with the Cubs. Upon winning a World Series with Boston in his final season he embarked on a second act that those who paid attention to him during pitching days probably could have predicted: serving as an analyst for MLB Network and Marquee Sports Network, where he hosts Off The Mound, a half-hour late night-style talk show.

Dempster jumped on a oft-interrupted Zoom with The Big Lead to talk about all things on and off the field, pausing long enough for a humble blogger to repeatedly ask small children to keep it down a bit.

Kyle Koster: Your career pitching record is 132-133. How much does it eat at you knowing that getting those 87 saves cost you a .500 mark?

Ryan Dempster: I don't know what I lose more sleep over -- that record or my .099 career batting average. They're both pretty tough to take. But I always say I was a starting pitcher who closed for a few years because the team needed it. As a starting pitcher I was above .500 so I can take that. Maybe I wasn't a good closer but I was a good starter.

KK: Off The Mound is an extension of something you debuted live at the Vic Theater back in 2018. Everyone who sits behind a big desk and has guests on has to develop their own interview style. What is yours?

RD: It's pretty laidback. I do ask the guys about moments in their career. I think fans want to hear about that. If you have a chance to sit down with Kerry Wood, he wants to talk about his 20-strikeout game and we can share that moment with fans, talk about what he was feeling. Or talking with Jon Lester on what he was thinking before Game 5 of the World Series down 3-1. But for the most part it's what the title says. It's off the mound, away from the field. It's who they are as people.

Playing with them for all those years I have that relationship and probably know a little something that not everyone knows. I try to get that out of them and share those real moments. At the end of the day we idolize them for what they do, but who they are is just as important to me.

KK: I think the first taste of your personality a lot of people remember is the Harry Caray impersonation.

RD: That started way back when it was younger and then went away for awhile. Then I saw Will Ferrell doing it on Saturday Night Live and I remembered doing it with my brothers while joking around so I brought it back. When I got to Chicago I tried to soak in as much Harry information as I could, talking to people like Pat Hughes and [Caray's widow] Dutchie to get as many stories as I could about the man. When Will does his impersonations they're funny and great but they're over-the-top, you know, with the moon made of cheese and so on. I wanted to know what Harry would really talk about it, what he'd really say.

KK: You took improve classics at Improv Olympic to sharpen your skills. What was the vibe like there? If someone asked for an autograph did you have to say yes and?

RD: For the first several weeks in my Level 1 class, no one knew that I played baseball and it was great. We just had fun and went through different experiences. Sadly I got too busy to keep going. I learned a lot about adjusting on the go and working through extremely uncomfortable situations. There were people from all walks of life who were trying to be actors or comedians or people who ran businesses who wanted to get out of their box a little bit.

After the classes I started doing armandos at Second City and standup in Chicago, New York, and New Jersey, tried to find clubs when I could so I could do some sets.

KK: What's a worse feeling: giving up five runs in the first inning or not getting any laughs out of the gate during a set?

RD: Giving up five in the first. It's hard to come back from that. There aren't too many times when you do that and still win the game. I can bomb early on in a standup routine and still finish strong and the crowd will forget about the grand slam in the first inning. In baseball, they don't forget about that.

KK: Who are your comedy heroes and who do you draw from?

RD: As a host, I love Johnny Carson. I used to watch the Tonight Show with my dad. I loved his personality, his interaction with guests. From a standup comedy perspective I grew up watching Eddie Murphy. As a father of four and someone who is in the media, I can't use the same language Eddie does so I have to watch myself there. George Carlin is another guy I really admire.

As I got a bit older I discovered guys like Mitch Hedberg and loved that sense of humor. Finding something dry in a very obvious moment in life and bringing it out. And then Chris Farley. To me, he was so incredible and over-the-top, doing whatever he could to get a laugh.

I remember doing the motivational speaker on The Best Damn Sports Show. Those guys had no idea I was going to do it and I just went for it. It was just this great moment where I was paying tribute to somebody that I admired and cared about missed a ton. He made me laugh even when he did the simplest thing.

KK: Man, The Best Damn Sports Show. You're going to send me down a rabbit hole here. I'll be looking up John Salley clips all afternoon, looking over that acting reel.

RD: The best was when I was done, I ran over over Tom Arnold and John Kruk, I'm goofing around and jumping on tables. I sit down and John Salley was on satellite. And he goes, 'hey, Ryan, now I see why your team [the Florida Marlins at the time] sucks. You're too busy taking acting classes.'

KK: Classic Spider. At what point during your playing career did you set your sights on doing media when you were done?

RD: The joke was always if the guys couldn't find me they should look in front of a camera. I was doing photobombing before photobombing was cool. I just always took to that. In high school I was an entertainer. If there was a party I was in the kitchen telling jokes for an hour, goofing around.

I wasn't a guy when the offseason came would shut it off. I watched the playoffs and World Series. I live for it and love it. As I was winding down my playing career knew it was a possibility and the first year out I ended up getting a job at MLB Network and getting 25 appearances -- enough to get your feet in. When you stay that close to the game you never forget how hard it is. The old joke is that when you get up in the booth the game gets a lot easier, so I try to remember what it's really like.

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KK: You strike me as a bit of the duality of man idea as an athlete. You seemed to have no problem having fun yet could turn on the switch and compete. What were you like on the days you pitched versus the days you didn't?

RD: I was different every fifth day. It was weird. I was still pretty relaxed. I wasn't one of those starting pitchers who you can't talk to on the day he's starting. I would come in at 4 or 4:30 for a 7 o'clock game and really shut down things around me. At that point it was go time and I got locked in.

At the same time I realized we were playing a game and had fun out there. I'm a super competitive person. I hate to lose at anything even if it's cards against my mom. That's just how I'm built. Sometimes I feel like the bad dad and think I should let my kids win. But my dad told me that he if let me win it wasn't really winning. I think there's a fine line there I need to walk.

I also respected guys who were playing. That was their time and it wasn't okay for me to just joke around and be the guy who keeps it loose. That's where you have to read a room. Some guys can strike out in a big situation and you can joke around with them and they'd be fine with it. There are other guys who if you did that, you should expect to get tackled. Reading that room and knowing who you can push buttons on and who you have to pat on the back is really important.

KK: What you're describing is managing personalities. Do you think that connectivity is why so many guys are going straight from playing to managing these days?

RD: Yeah, I think so. What we're learning, especially as the game is evolving, and media has evolved with the access and amount of media. If you go back 50 years, a manager managed the game and had a couple of print reporters who followed him around. If you played in a small market you might've only had one or two. So the interaction throughout was mainly baseball, your players, and coaches. Now, it's a lot of interaction with a lot of different people.

I talked to [Baltimore Orioles manager] Brandon Hyde, who was a base coach with the Cubs. After his first year there I asked him what the hardest part was. He said it was the talking. You talk all the time. You talk from the minute you get to the field to the minute they say play ball. The minute you show up in your office, a player comes in because they're not in the starting lineup or the trainer comes in because someone is hurt. The pitching coach comes in. The hitting coach comes in. The infield coach comes in. Then you go out to the field and you deal with the media. Then you have to go around and connect with each one of your players, which is so important.

This spring training, I really paid attention to that with David Ross. The requests and asks of his time to speak about maybe the same issue throughout the day with so many players. I think the coaches and managers who are able to step off the field right into managing is a lot easier these days because they were accustomed to that. And they can relate to the current player because two years ago they were hearing them speak on what they wanted from a manager.

KK: There's a tremendous amount of game-planning that goes on in-between starts. Did you have a similar plan of attack for what you could do on the media side, like which boxes you could check or provide something different?

RD: A little bit. Not so much my first year. I was strictly doing the TV work with MLB Network. I was trying to relay things that I knew about having just come off the field that maybe someone who had been doing it for 10-15 years wasn't privy to.

Then the next offseason I took a job as a special assistant to Theo [Epstein] and Jed [Hoyer]. I was able to be around them and observe the front-office side of things. To see how hard they work and how much they care about the players on the field and giving fans a winning product. I was fortunate to learn from the best in the business of baseball operations in addition to having the history as a player that allows me to be analytical. I feel very fortunate and blessed that I've been able to learn baseball from all these different angles.

KK: What's special to you about Chicago? Why have you made it your home and what made you want to join a network based there?

RD: Playing nine seasons and raising my family here, the people have treated me incredibly. They supported me when I was on the field, supported the charitable foundation we have. They've been incredibly generous and kind. There's something about the Midwest. They're down-to-Earth people.

I won a World Series with Boston in 2013. I'll forever feel like a Red Sox player but at the core of me, I feel like I'm a Chicago Cub for life. When you get a chance to play parts of nine seasons in one place, that's rare. When the opportunity came up, I jumped at it. With Marquee, they were supportive of me. They knew I wanted to do the Off The Mound show with, originally, a live theater and studio audience. Obviously with a global pandemic we're not doing that but hopefully we'll get back there at some point.

KK: So many people from outside of Chicago grew up with the Cubs because of WGN and being able to see the broadcasts. And they grew to know them as the lovable losers, like the feel-good opposite version of the New York Yankees. What's it like to be part of covering what has really morphed into a specific global brand?

RD: Yeah, it didn't matter where you were. Will Ferrell and I talked about that. He said he could come home from school early and the game would be on there in L.A. You could be on the West Coast or Montana or Texas. It didn't matter. Especially with all the day games it was the only one going. To this day it's the only game going on a Friday afternoon. It's nation- and worldwide. So what happens is you travel well.

When you think about Wrigley, too, nowhere else is like that. A stadium in a middle of a neighborhood, surrounded by bars, restaurants, and stories. It's a like a Monopoly board of all these buildings. So you create these friendships in the neighborhood. There's a large circle of "friends." It's always had that feel. I've always live nearby. I walked to the ballpark 90 percent of the time. You'd walk by people outside playing bags and they'd offer you a beer.

KK: If someone could bottle up that feeling of a Friday afternoon at Wrigley and sell it, they'd be obscenely rich.

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KK: You have a Ferris Bueller Day in Chicago. No work. No responsibilities. What do you do?

RD: I'm getting up in the morning and going for a little brunch at Toast. Then I'm taking in an afternoon Cub game. I'm hoping I have a friend who has a boat and is going to park it out in the Playpen then cruise the Chicago River. Drop me off at Chicago Cut. I'm going to crush a full meal there with a steak and a few glasses of wine. Then I'm going to make my way at some point to a little speakeasy called Brando's. It's a one-of-a-kind karaoke bar in the South Loop.

KK: You played for the two teams with the most notorious championship droughts in sports. Do you ever stop and think about all the players who played in Boston and Chicago but didn't get to experience the payoff after a lot of suffering?

RD: Absolutely. Even to think of all the great ballplayers that I personally know who played for the Cubs and didn't get a chance to win. The 1969, 1984 and 2003 teams. Then going to Boston and thinking about Ted Williams, who didn't get a chance to win a World Series there. And then here I am playing one year and feeling like I got to play there for 10 years because we got to win a championship after an incredible season. We did in Boston, in front of the home fans for the first time in 95 years. It was really, really special and something that doesn't just fly over my head.

I did appreciate it and I didn't take it for granted. That was my last year. My 16th year in the big leagues and it was my first trip to the World Series. I know hard it can be. I saw all the great players I played against who never got there and some who barely got to play in the postseason. It was truly incredible to play in two iconic places like that.

In 2016, when the Cubs won the World Series, a lot of those guys on that team said it was for me and the other players who came through. It was for us, too. It was for the guys who grinded through the curse of the goat or black cat. Man, you talk about being appreciative. It's so easy when you're playing to think of me, me, me so to reach out to the guys who came before them was pretty cool.

KK: Okay, Ryan, that's a nice thought and all but I want to get dark here. Let me tell you about the worst moment in my life as a sports fan and how you're involved. It's Game 2 of the 2013 ALCS and the Detroit Tigers have a commanding 5-0 lead, well on their way to a 2-0 series lead. And then something awful happened. Can you tell me just how close Torii Hunter was to catching that ball? What was your angle on it?

RD: It was caught by my bullpen catcher, who was warming me up at the time. Dana Alan LeVangie was our bullpen coach. So we're down 5-1 when that inning starts. He tells me 'Demp, you're warming up.' We get a few runners on, I keep warming up. Another runner on, I'm still warming up.

Junichi Tazawa starts warming up as well. Dana looks at me and says, 'hey, Demp, if we score one you're still in. If we score two, then Taz is in.' Now, I'm on the rail closer to the field and Dana was looking right at me. So I made this comment to the effect of 'I can pitch down three but I can't pitch down two, I'm going that good?'

I come set with my glove on my next pitch and look Dana in the eyes and say, 'hey, Dana, what about when we score four right here?' I picked my leg up at the same time [Joaquin] Benoit picked his leg up to throw his pitch to Ortiz. There are different replays but there's one that shows the pitch get caught by my bullpen catcher and he changes the ball into his other hand, looks up to his left, and catches the home run ball. All that happens in a second.

And now, of course, we're excited. We have this Boston cop with his arms up, getting his 15 minutes of fame. I remember running down there talking to Torii to make sure he was okay. He had the wind knocked out of him. I told him he was such a stud for even trying to make that play. I probably shouldn't have thrown a 'sorry you didn't catch it' in there -- he probably didn't want to hear it at that moment. There was shock on my face because as a guy warming up you see all this transpire and a guy flip over the wall.

KK: I maintain it's one of the most stunning postseason moments and a reminder of why baseball is so great -- even if it did take me to the Sunken Place.

RD: I was just watching because it re-aired the other day. When you're in things you tend to forget a little bit. Watching it I remembered we were no-hit in Game 1 until the ninth inning. Then in Game 2, Max Scherzer had a no-hitter until two outs in the sixth inning so it was domination of a potent lineup by this pitching staff and then we had Justin Verlander in Game 3. So we knew we had a tough road ahead.

I remember the feeling of relief when Scherzer left. He had over 100 pitches but I thought he might go back out. The minute he didn't, the switch flipped from 'we're getting dominated' to 'we have a chance to come back.' As a pitcher I understand all the analytics and it would have been the third time through the lineup but when a starter is mowing people down, let 'em go 150. Sometimes you're only as good as your starting pitching and as soon as he left our team started believing.

KK: Yep, that's Jim Leyland. A slave to the analytics if there ever was one. What a fun trip down memory lane for me. Not sure why I brought it up.

Off The Mound episodes are available here and are also available as a podcast wherever podcasts are available.