Ryan Dempster Is All For More Personality, More Rivalries, And More Dustin Pedroia Stories
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What does Ryan Dempster believe about personality in baseball?
One of the best.
Rob, how are we doing, dude?
I'm good. I'm good. You are everything that is right in the world and also in the world of baseball. It's always good to see you, man, out and about. It's big games. You know it's a big game if Ryan Dempster shows up.
I love it, man. The community that we have within the baseball world and the faces that we see, obviously the players playing the game is one thing, but all the stuff behind the scenes that we run into, writers and broadcasters and people who've been covering the game forever and agents and former players that are back on the field. It's awesome, man. It feels like a parade every day. You know, every time we're all getting together, it's really cool.
Well, that's the thing. When I saw you at the World Series, that certainly was the vibe. And now we get the winter meetings coming up. And I think that that's one of the things until I started talking about it that you realize this is what's special about the winter meetings is, yeah, you get the rumors and you got potential deals, but it's also the sense of community. I mean, this is the time, right? I mean, you've done it.
it's incredible it's so much fun you're trying to figure out who in the hotel bar you can charge your drinks to you know because there's so many intertwining connections like that guy owes me a drink i know for sure he owes me a drink two over there so you're just room charging all over the place but um no it is listen i mean the winter meetings are exciting when players are signing like that's the facts right and when and we got that action role and then you got everybody and all the insiders and you know, whoever that might be, right? Like maybe Kenny Rosenthal is popping out of a shrub somewhere like this Butler and Mr. Deeds, you know, like never underestimate.
How are rivalries like Red Sox vs Yankees relevant today?
I remember when we were, when the Cubs are trying to sign John Lester. Oh yeah. San Diego, San Diego. Yeah. I'm like, where were you hiding bro? In a trash can? Like, how did you, I didn't even see you. You're like a Ninja. It's incredible. I admire your Ninja skills. So, but it's just a fun time. And like you said, all of the, all the stuff going on. We have this lull from, the end of the World Series until the middle of December when the winter meetings happen. So then it's like, oh, now we get into that excitement. Let's go. Let's see who's hiding where. What president or general manager is not coming out of his suite? There's a lot of missed opportunities too, Rob, by the way. There's a missed opportunity, I think.
Every time they're in San Diego, if I'm the top free agent – I'm renting a yacht out in the middle of the ocean, and you have to come either via paddleboard or you have to come via jet ski. Oh, like can, right? Yes. Let's go. That's how it's got to be. You got to come out and swim out. I'll sign with your team. If you make it past all the great whites and all the sharks down there and you get out to my boat, I'm signing.
It's funny you bring up San Diego because that was where – That was the Lester deal was. Like, that was it. I remember, because I remember speaking of Rosenthal, him and I followed Seth Levinson into the elevator. So it was me, Seth, and Rosenthal, like, leading into what ultimately became this all-nighter, which I don't know if you were a part of, probably. But this all-nighter to get John Lester, convince John Lester to come. Yeah, so... That was crazy. That was crazy.
And when you awkwardly get in the elevator because you're trying to get something from somebody, but you need the key to get to your floor, then you're doing this one. Like, where did I – that's weird. Hey, what floor are you on? Me too. No way.
What unique stories does Ryan Dempster share about Dustin Pedroia?
Listen, I know that there's – you're probably membership to many, many elite clubs with many leather-bound books, many airport – airport statuses and everything else. I am not. But that elevator ride made me feel very special. It was three people, and it was the people who I would say, these are the two people I want in the elevator right now. Yeah, perfect.
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Chapters
7 chapters
1
What does Ryan Dempster believe about personality in baseball?
0:00–1:42
2
How are rivalries like Red Sox vs Yankees relevant today?
1:42–3:36
3
What unique stories does Ryan Dempster share about Dustin Pedroia?
3:36–7:07
4
What makes the Winter Meetings special in baseball?
7:07–14:26
5
How does Ryan Dempster view the role of competition in baseball?
14:26–19:16
6
What insights does Ryan Dempster provide on the World Baseball Classic?
19:16–24:32
7
Why are emotions in baseball important according to Ryan Dempster?
24:32–32:18
Speakers
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