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Baseball Isn’t Boring

Lessons From The Alex Bregman Signing

12 Jan 2026

Transcription

Chapter 1: What surprised everyone about Alex Bregman's signing with the Cubs?

0.031 - 2.794 Rob

Yeah, there should be some passion. This doesn't have to be boring.

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3.315 - 8.822 Matt Spiegel

You don't get bored by baseball. Okay, one thing the game needs is more people like you. You. You. You. You.

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9.022 - 10.444 Rob

You. You. You. You.

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11.865 - 20.957 Matt Spiegel

You. You. You. You. You. You. You. You. You. You.

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21.437 - 52.903 Rob

You. You. There's absolutely no human being on the planet I would rather be talking to more than Matt Spiegel right now. My man. I mean, by the way, 670 score, the straw that stirs a drink when it comes to all things Chicago sports and everything else is good. But, you know, I'm glad that you texted after the Bregman signing. I don't know if you know this, but Alex Bregman's going to the Cubs.

53.407 - 78.09 Rob

But but, you know, me, I'm so glad you did, because I'm like, I'm like, yeah, we got to talk. We got to talk about this. We got to talk about this. It's incredible. So, Matt, like it's it's not ironic, but weird, because a week ago we did this power ranking of of. I guess it was the most desperate teams or the desperate fan bases in the offseason.

78.871 - 107.024 Rob

And I said, I think the most confused fan base is the Chicago Cubs. And because I think, and you correct me if I'm wrong, but from my perspective, a week ago, it was, we're kind of linked up with some people, but we don't really believe it. And we've done some stuff, but it hasn't been really a lot. And then, boom, a week later, nobody's confused anymore, right?

108.066 - 136.082 Matt Spiegel

No, it's pretty clear now. Yeah, no, man, you're right, and it's been going on since the end of the season, which kind of restated the needs that were so clear at the deadline that they didn't go for. Like, they needed a front-of-the-rotation caliber righty arm really, really bad. And everybody knew it at the deadline. And they didn't get it.

136.483 - 165.575 Matt Spiegel

And then in the playoffs, they had a nice little run, but then it was exposed when they needed another great arm and they didn't have it in that game five and it cost them. So all of that came back. And also, literally the day after they lost in the playoffs, I did a segment on our show Do the Cubs win that series with Alex Bregman? Ooh, look at you.

Chapter 2: Why did the Cubs decide to sign Alex Bregman?

165.916 - 195.362 Matt Spiegel

Because I know that they wanted each other, right? That Bregman wanted the Cubs and Jed wanted Bregman. And Tom Ricketts only authorized, what, four years and 115 mil last year, and he goes to Boston for three at 120 with the opt-out. And there was a moment in that playoff series against Milwaukee where Kyle Tucker took a walk, and there was nobody after him.

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195.73 - 218.059 Matt Spiegel

And there was another moment where Kyle Tucker had a terrible at bat. And I mean, it's like you needed Bregman so obviously and so desperately. And that match should have happened. But then as the offseason went on, man, I didn't think it was going to happen. And I did multiple segments of like, Cubs, what are you doing? This is a win now moment.

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218.039 - 247.439 Matt Spiegel

With one year left on the agreement between the players and the owners, one year you just re-upped with Jed Hoyer. Your team is good. You should be going for it right the hell now. And their offseason was not that of a team that was going for it. So but now here we are today and they traded for that power arm in Cabrera as risky as it might be. It's still an aggressive move.

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247.86 - 264.557 Matt Spiegel

And, you know, that kid has probably a higher ceiling than Dylan Cease, maybe even Michael King. Right. And some of these other guys, certainly Zach Gallen. Like, I'm glad they went and tried for Cabrera. It's going to be fascinating.

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265.138 - 265.258

Right.

265.238 - 284.68 Matt Spiegel

And then they needed a bat desperately, and we're like, wait, are they really in on these guys? And here they are. So Cabrera and Bredman, sure, the other bullpen moves, they kind of fit in just fine, the ones that are made. Maybe there's a little bit more to do. But, yeah, the offseason makes a hell of a lot more sense.

284.841 - 296.934 Matt Spiegel

And they went from probable favorite to win the division to now right up there with the Dodgers. Oh. the Phillies or anybody in the national league?

296.954 - 318.905 Rob

There's no question. There's no question. And, you know, it's, I think it's a great lesson. Well, I guess, you know, it's a great lesson when ownership signs off on it, because I'm sure some GMs would love to do this sort of stuff, but you need sign off. Ultimately you, you, they make the Cabrera booth. Okay. Good for you. Good job. Excellent job.

319.085 - 323.992 Rob

Like great point by you about this is better than what you could have gotten free agency.

Chapter 3: How did the Cubs' offseason strategy change after signing Bregman?

519.875 - 539.578 Matt Spiegel

Right. Welcome to modern... Big city behemoth baseball. Thank you. Welcome. It changes things. Because with the deferrals means they can stay under their first level of the CBT if that's what they want to do. Maybe they don't have to trade Nico Horner, which they shouldn't do. You know what I mean?

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539.558 - 565.068 Matt Spiegel

There was there was this feeling of doom, like not only are they not going to sign the big free agent, but they're going to sign somebody else, you know, and then also trade Nico and do this kind of mealy mouth good enough to win the central thing. And that's not where we are. Tom did it. You cannot say anymore that Tom Ricketts won't pony up and get the big money free agent.

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565.088 - 568.837 Matt Spiegel

They did five for 175. It's 70 million at deferrals. Unbelievable.

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569.178 - 591.081 Rob

So you mentioned last year. Let's go back to last year. There was some talk that they didn't want to do deferrals. They didn't want to enter the world of modern baseball. As you said, when you look at the Bregman, how that shook out last year, it was, yeah, Detroit offered the most years. He never wanted to go to Detroit.

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591.601 - 607.018 Rob

And also, by the way, congratulations, Scott Boris, for understanding, hey, you're doing this. He's done this a few times now. You get the opt-out, the one-year opt-out, get the qualifying offer off, and then here we go.

607.038 - 614.245 Matt Spiegel

How about Blake Snell made a mint after the one-year? Matt Chapman, right?

614.266 - 643.223 Rob

He's got it down. We didn't even see this, but we should have seen it. This is like Scott Boris for all the criticism he gets. Like there are certain things, certain times where he's revolutionized what's going on. What he did was smart. You mentioned it. Snell, Chapman, Alonzo. So this is what I'm going to come back to where the tipping point for Bregman last year was the opt-outs.

643.243 - 671.961 Rob

Like that was it. The tipping point, the Red Sox acquiesced. for the opt-outs and i don't know if the cubs i don't think the cubs had agreed to that they had not only not only are there oh last year i don't think they had the opt-outs no they didn't want to play that game no exactly yeah and but so that was last year so it has flipped like so The Red Sox acquiesced to the opt-out.

672.281 - 691.887 Rob

They say, hey, we traded for Crochet, and we're going to pay. We don't mind paying $120 million for three years, even though it only might be $40 million for one year. We don't mind that. We're going to spend money. We're going to go for it. And now everything's flipped, where the Cubs, to your point, Tom, congratulations. Tom Ricketts, good job.

Chapter 4: What mistakes did the Red Sox make in their pursuit of Bregman?

868.969 - 879.861 Matt Spiegel

Maybe you want to lock in at five or seven years in a big one. But, you know, the money is so big, you could just kind of pick and choose and pick your situations and try to win every year. That's sometimes the way you got to do it.

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879.881 - 901.774 Rob

Well, you know, and I think what it comes down to, whether it's a year or whether it's five years or whether it's seven years. It is about trying to win and understanding that's the goal. Understanding it's going to get uncomfortable. Uncomfortable. I've said it a million times. We have the quote from Andrew Friedman. I'm going to paraphrase because I have a terrible memory.

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902.214 - 910.288 Rob

But like you said, something effective. If you're logical about free agency, you're always going to finish third in free agency.

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911.129 - 940.359 Matt Spiegel

This was the Cubs. It's been the Cubs for a while now. The Cubs have been analytical, and it's felt like Carter Hawkins brought a Cleveland mindset in here. It felt like Jed Hoyer had kind of sold his aggression. for an extension and a continued relationship. And then you see this and it's like, all right, there is some smart stuff going on.

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940.499 - 966.277 Matt Spiegel

I feel a lot better about giving up Owen Casey for three years of Cabrera I don't worry about the other two kids, but I feel good about that cost. I feel a lot better than hoping that Tatsuya MI is from Japan is good enough for the money that he's going to get. Like I'm cool, especially because Cabrera is making three and a half million next year.

966.858 - 980.159 Matt Spiegel

I mean, so that's part of why you can do the Bregman thing is because you're being efficient in other ways. So if they're going to be a blend of choosing their efficiency here and And spending big there, I'm totally cool with that.

980.179 - 999.473 Rob

I'm just, and you're right. And as you're talking, I'm thinking about the Cubs, how they altered, how they evolved, or not evolved, but changed. And now I can think of when they went out on Lester. I remember being in the winter meetings in San Diego. Like, that was, we're going to find a way to get the guy. We're going to get the guy.

999.807 - 1023.681 Rob

Like there is, and I can obviously, when we look at the modern day baseball, Dombrowski is, we're going to get the guy. AJ Prowler is, we're going to get the guy. But there's too many front offices now. They're modeling it, Matt. They said, this is our model. We can't do that. We just can't. We can't. We can't. It doesn't make any sense. Well, of course, free agency doesn't make any sense.

1024.222 - 1039.627 Rob

But to come back to your point about the importance, think about what you said about Alex Bregman. Would they have won with Alex Bregman? What you don't want to be is that team saying, would you have won if we had Alex Bregman and you don't have Alex Bregman?

Chapter 5: What impact does Bregman have on the Cubs' lineup?

1207.038 - 1227.302 Rob

Understand of what it takes to get through that. Understand how the clubhouse, someone in the clubhouse to do that, how important it is to have someone. Look at the Phillies. Look at the Dodgers. Look at even the Blue Jays last year. There's a lot of adults in the room. Alex Bregman is the ultimate adult in the room. And I don't know how much the Cubs needed that.

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1227.569 - 1232.385 Rob

But absolutely, that is a feather in the cap.

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1232.425 - 1256.651 Matt Spiegel

Here's how much they needed it. They kept Justin Turner on the roster all year and kept Justin Turner on the playoff roster even though he couldn't hit a lick. I mean, because he brought that and they admitted that it was important. And the fans and the media understood that it was important. This is a better fit than Justin Turner. This is why Schwarber is a legend.

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1257.252 - 1273.635 Matt Spiegel

Because Schwarber has all of that and produces, right? And so are some of those other guys in Philly, too. So if Bregman has all of that and produces... that's when the value really jumps up. Can I give you a Bears story from last night that'll fit?

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1274.397 - 1290.702 Matt Spiegel

When you sign the free agent veteran, like the Bears did with Joe Tooney, the guard, former Patriot, or Grady Jarrett, the defensive lineman, the former Falcon, you're dreaming of a moment where they can teach the young kids how to win, right? And it's kind of abstract and it's ethereal. And like,

1290.682 - 1307.745 Matt Spiegel

Alex Bregman has won two World Series in Houston, and you're dreaming of some way he's going to help these guys win. Helping Roman Anthony with his swing is really specific and wonderful. In the Bears game against the Packers, they're down 21-3 at the half. At halftime, both Joe Tooney and Grady Jarrett knew this year.

1307.843 - 1324.654 Matt Spiegel

were able to talk to the team about what it's like to be up 28-3 or down 28-3 in the Super Bowl with the Patriots and the Falcons and talk to them. And apparently that changed the mood and the possibilities at halftime. You never know when there's going to be an exact moment.

1324.634 - 1350.76 Matt Spiegel

where the veteran who's done it is going to be able to transmit something that changes the fate of your freaking franchise so bregman will have stuff from two world series wins in houston and i'll have stuff from a competing year with a new club in boston that he's going to bring to the table that's going to matter we don't know what it is but you know it's going to happen that's how it works yeah no active play i don't think any active players played in more playoff games

1350.74 - 1366.215 Rob

He's made the playoffs every year, and I don't think – and it's easy to say, hey, you know, that you get a leader and you make the – it's not always that easy, but I don't think that's a coincidence that he's making the playoffs every year. Yeah, he's on good teams, but it's not a coincidence.

Chapter 6: How will Bregman's experience influence the Cubs' younger players?

1596.738 - 1609.38 Rob

Is there any... As you see it right now, are there any holes that need to be filled? I guess this is my way of saying, where does Alex Bregman hit? I don't know.

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1610.541 - 1636.521 Matt Spiegel

Here's the thing. In terms of the lineup itself, towards the end of the year, Nico Horner was hitting leadoff against lefties and Michael Bush was hitting leadoff against righties. So I think it's going to change from day to day based on what Council and Hoyer feel. But Bregman is, you know, he's like a top three, top four bat to start.

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1636.822 - 1658.391 Matt Spiegel

and probably against either side, and we'll see what the performance is. And they'll also take a look at his swing and the plane of his swing versus certain pitches and use all the modern stuff they use on a day-to-day basis. And I'm cool with all that. But I think he's certainly a top three, top four hitter against either lefties or righties from the get-go.

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1658.573 - 1682.059 Matt Spiegel

You know, there really was only third base, potentially, as a place where the Cubs could improve. We thought right field was going to be Owen Casey and Seiya Suzuki, and with Moises Ballesteros getting a lot of DH work, that the three of them would essentially split up that right field stuff. Maybe a little Kevin Alcantara, young player.

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1682.399 - 1682.539

Mm-hmm.

1682.519 - 1705.523 Matt Spiegel

That runs well and fields well. But third base was handed to Matt Shaw last year, and he didn't really play well enough to deserve it by the end of the year. And so he's a good young player, but you're going for it. You've got him under salary control. Matt Shaw should be a super utility guy this year, and I hope that's what it's going to be.

1705.823 - 1729.84 Matt Spiegel

So I wanted either Bregman or Eugenio Suarez even on a short-term flyer. Like, go get me some bombs at third base and let Shaw be a super utility. I think that'll be the case now. Nico Horner at second. Dansby Swanson at short. Maybe Dansby can have a few extra days off. And Nico can play short, which he does very, very well. And Shaw can play a little second. Or Bregman can play a little second.

1729.82 - 1748.572 Matt Spiegel

and they can mix and match it a little bit, give guys some days off. But Shaw, I hope, will also get an outfield glove and learn how to play the corners a little bit so he can be that super utility, get a shot out and right every once in a while. Ian Happen left. Seah played really well in right field last year, so I think he'll get a lot of looks in right field.

1748.612 - 1771.324 Matt Spiegel

And Pete Crowe Armstrong will play every damn day in center because even when the bat doesn't work, the defense is platinum glove caliber. Look, it's a really good and impressive lineup, and the defense is outstanding across the board. And Matt Shaw should be that guy who plays all over and just helps you fill out your roster. You should have a roster that doesn't have any holes at the bottom.

Chapter 7: What are the potential challenges of Bregman's contract for the Cubs?

1888.491 - 1889.072 Rob

Thanks, man.

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