The World Series is almost here, and few people understand what the Brewers and Rays pulled off better than David Samson.
Samson was president of the Florida Marlins when they won the 2003 World Series with one of the lowest payrolls in Major League Baseball. More than two decades later, Milwaukee and Tampa Bay have reached the Fall Classic from the bottom half of the league’s payroll rankings, and they’ve done it with MLB’s Collective Bargaining Agreement set to expire in December and a work stoppage widely expected.
Samson, now a regular on The Dan Le Batard Show, Pablo Torre Finds Out, and CBS Sports HQ, and the host of his own podcast, Nothing Personal with David Samson, spoke with Awful Announcing ahead of the Series.
Note: This interview has been edited and condensed for length and clarity.
What stands out to you first about this World Series?
David Samson: “It’s the two best teams in baseball. The No. 1 seeds have met only nine times in the 44 years since the Brewers were last in it. And I hope it shows the entire world what good baseball is. What fundamental pitching, speed, and defense are. How to build a team with depth, with players who play together and sacrifice themselves for the betterment of the team. How to build a bullpen. The importance of starting pitching, which people think may not matter anymore, but it does. We can talk about the labor side of it, because I think most everyone in the media is getting it wrong in terms of what this means for labor. But, from a baseball standpoint, it’s going to be an outstanding World Series.”
How are the Brewers winning?
“They have a system they stick to. They have a community that supports them, which enables them to have a payroll that, in theory, would be greater than what the size of their market would allow. They make incredibly disciplined decisions. And they don’t allow the emotion of a name on the back of the jersey to overtake smart baseball moves.
“For example, when it’s time to trade Josh Hader or let him go because you have Devin Williams, you do it. When it’s time to let Devin Williams go, you do it. When it’s time not to re-sign Willy Adames, you do it. And while that can be painful, the reality is, it’s not because they do it right. They’ve won their division four years in a row and have been in the playoffs eight of the last nine years. The two teams in the World Series are great examples of how to build a team.”
What about the Rays?
“The Rays were in the World Series in 2020. They have one player from that season, Yandy Díaz. That’s it. Everybody else is new. So, I guess it means we should all be cheering for the (name in) front of the jersey and hope your front office is super smart. They put a lot of money into people power. There are a lot of people who are really good at what they do. They are not, by any stretch, 100% analytics at all. I know Matt Arnold. I interviewed Matt Arnold to be the GM of our team. We went in a different direction then, but I knew he was going to be a star. To win in baseball, you have to do it all. The Brewers and Rays do it all. They have smart managers, smart front office.”
Do you have a prediction for the World Series?
“Brewers in six. When I look at the Brewers bullpen, the caveat is that if the Brewers bullpen gives me four more games where they don’t give up runs, they’re going to win four more games. They’ve gone through the playoffs, and you can’t score off them. I find it hard to imagine, even with how great (Drew) Rasmussen is, how great (Freddy) Peralta is. And by the way, Griffin Jax is no schlepper, and neither is Nick Martinez. But I look at the Brewers 1-26, and I give them the advantage, but it’s slight, which is why I say six games.”
Will having two small-market teams in the World Series affect labor negotiations?
“It doesn’t impact the negotiations because the owners, from the beginning, have said it’s not about one year. It’s about a larger sample size, where the difference for a small-payroll team is between 80 million and 400 million, and you can pick whatever number you want because there are a million different numbers flying around. But the difference between the Marlins and the Dodgers, you’ve got to make that difference smaller, like the other sports, in order for all 30 cities to believe that they have a chance. It doesn’t mean, and this is where the confusion comes, that you’re never going to legislate away stupidity. There’s going to be teams like the Mets, teams that have huge payrolls that don’t win. And you’re always going to have teams like the Rays or the Brewers, where, on this lower end, they’re going to win.”
As someone who appeared on several Pablo Torre Finds Out episodes about the Clippers-Kawhi Leonard salary-cap circumvention scandal, what’s your main takeaway?
“Here’s the equivalency in my mind. Many people spend time with accountants trying to figure out, ‘How do I pay less income tax?’ You hire lawyers and accountants to be as efficient as you can be within the four corners of the tax code. ‘Where can I be aggressive?’ There are many ways to interpret provisions of the tax code where you can be aggressive or conservative.
“The salary cap is no different. There are groups of people employed by every NBA team for the sole purpose of maximizing the amount of dollars they can pay players under the rules of the salary cap. … ‘How much can we stretch the salary cap? What can we do here? Both that we disclose, and that we don’t disclose but that it’s very inbounds, meaning we don’t flaunt it.’ The problem with Steve Ballmer is that he flaunted it in a way that was sloppy. And then once he got caught by us, he then lied about it.”
What’s it like being on Pablo Torre Finds Out?
“There have been shows I’ve done with Pablo where I’m aware of what’s going on, but I don’t know what’s in the folders. And there have been shows I do with Pablo where I don’t know what’s going on, and there are no folders. The beauty of my partnership with Pablo is that we make good shows together, and we’ve enjoyed doing it for a long time. I remember talking to Pablo when he was thinking about Pablo Torre Finds Out. I’d been doing Nothing Personal for years, and we were talking about what would be interesting to do. It started with, ‘Well, let’s do the serious things stupidly and the stupid things seriously.’ That’s what Pablo and I would talk about from the very beginning, and it’s evolved into a show where you can talk about salary-cap circumvention one day and making your head out of butter another.”
How has Nothing Personal changed since you started it?
“The first show was listened to by one person, my mother, and that’s a true story. I think we had about four downloads for the first episode, and it wasn’t on YouTube. It was literally that in October 2019, and now we know how big it is. So the question is: does the audience realize how much I depend on them, just as they depend on me, and that I take comfort in them and have such great appreciation for them? I hear from new audiences who have just found the show, and I find it fascinating and amazing that people keep finding the show. Then I get to start a new relationship with a new audience member that I can become codependent with, and it just grows like that.”
Yesterday, my daughter, Kyra, passed away peacefully after a 9 month and 11 day fight against one of the cruelest diseases I’ve ever seen up close. She was diagnosed with Brain Cancer, specifically Glioblastoma. I have felt all of your concern and love for these months and wasn’t ready to be anymore specific than I was.
Kyra was a 28-year-old young woman who loved deeply and who is impossible to describe in 280 characters. While her life got stolen from her, she handled these months with courage, poise, and resolve. And all I want is for no family to feel what we feel today. For no young person to suffer the way she did.In lieu of flowers, if you are moved to make a memorial gift, please consider “The Kyra Fund” (https://t.co/4bl8cxV1Dt)
This fund will be used solely to research treatments for Glioblastomas.
— David P. Samson (@DavidPSamson) June 24, 2026
Our condolences on the passing of your daughter, Kyra. Did you think about not doing the show following her death?
“I didn’t do a show from June 23 to September 8, and I remember very clearly professionals telling me, not in the entertainment business, in the therapy business, that that’s pretty soon to come back. Like, ‘Are you sure that you’re ready to come back?’ My answer was, ‘No, I’m not sure I’m ready to come back, but I don’t know what else to do.’
“Kyra was in the entertainment industry. She was the production coordinator on Jeopardy! and the production manager on Watch What Happens Live With Andy Cohen. We talked about the entertainment industry, and the concept of ‘the show must go on,’ but we never talked about it in these terms. I think it’s a trope to say, ‘I think Kyra would want the show to keep going, would want you to keep doing it.’ I guess that’s right, but I’d give anything in the world to ask her that question.”
How can people support you and honor her memory?
“We started The Kyra Fund. It has raised almost a million dollars, and we’re not going to stop. Pablo’s been great about helping to raise money for it. Kyra’s mother thought quickly to start a fund, and we started it the day after Kyra died. We’re going to raise money; 100 cents on the dollar goes to research to find a cure. A 27-year-old shouldn’t die of glioblastoma. It just can’t be.”
To donate to The Kyra Fund, please visit here.
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