The Milwaukee Brewers are World Series champions.

A five-game win over the Rays gave Milwaukee its first title in franchise history, and the 2026 season is officially in the books.

But the offseason doesn't wait. Free agency opens tonight, and the CBA expires Dec. 1, which is likely to trigger a flurry of activity this month. So we pulled Jolly Olive off the mic to look back on the season, tell us who has the most riding on this winter, and make his free agent picks.

How did the Brewers do it? Who's headed where? Jolly walks us through it all below.

JOLLY: I was definitely part of the brigade on that front. I think a lot of people thought they would be there, but not a lot of people thought they would stick the landing in the playoffs, because that's been their track record.

I think what it really was is they finally won the game they usually lose. The game I’m talking about is the Mason Miller comeback game. That was an earned comeback win. They were down to their last out. I think it's one of the best wins in the history of their franchise, and a lot of fans said after that game that it felt like it could be real this year.

Last year they beat the Cubs and that was huge, but after getting pretty dumpstered by the Dodgers, a win like that against San Diego, going up 2-0, defending home field, everyone contributing — that's the kind of win that can really propel you to win a lot in October. And they got it early.

JOLLY: Yeah, I think so. Maybe some are not very different than the takeaways that you'd see from, like, when the Guardians make the CS: It's that we shouldn't ignore defense, we shouldn't ignore athleticism, we shouldn't ignore speed.

But the bigger takeaway that some teams might begin to look into is your manager matters a lot. I think we kind of brushed that aside for a little bit —a lot of teams, not just big-market teams that haven't performed well. But someone like Pat Murphy was integral to what the Brewers did, and I don't know if they do it without him. Not so much in the way he's constructing lineups or using his bullpen. It's more that he got this team to be a family and believe in each other and ride or die for each other.

Sal Frelick, in his post when they got to the World Series, said he's going into the World Series with his best friends, and I thought that was very telling. Not everybody's best friends in the clubhouse at all times, and I think that has a positive, tangible effect on how your team performs in really important, stressful games like the playoffs.

JOLLY: It's interesting. This felt like a transitional year. A lot of the guys who've had strangleholds on MVP, like Aaron Judge and Shohei Ohtani, it wasn't their year this year. A lot of the teams we kind of expect to be there at the end every year also took a step back. The American League was just weird this year in general.

But yeah, I think you are seeing a changing of the guard a little bit. The era of the Astros dominating every year is by the wayside. The era of teams getting to the end and then getting right back there — we saw with the Blue Jays, it didn't really happen for them this year. The Phillies — their era might be closing a little bit. They'll need to kind of reinvent and redefine themselves.

I do think you're seeing baseball in a little bit of transition, but I don't think it's clear who's going to end up on top of it. It still very much feels wide open. If you asked me right now who I thought would be in the World Series next year, I would have no earthly clue. So it's kind of a land of opportunity, but it's also scary considering the labor negotiations, because that land of opportunity could go by the wayside kind of quick.

JOLLY: I think it's going to be the busiest November we've had in a while, because a lot of players are going to want to get their deals done before a labor negotiation possibly changes what they can earn or how they can earn it. So you're going to see a big flurry in November, and it's going to be on teams that aren't afraid to spend in what could be a partially lost season. I think you'll see a lot of the big-market teams make those moves.

When we last had this in 2022, we had a mix of both: the flurry in November and then another flurry right before Spring Training. That was the year Corey Seager and Marcus Semien went to the Rangers. I think that was the Kris Bryant year as well. A lot of big deals, a lot of financial security for the players, and they definitely won that labor negotiation. I wonder how it'll be different based on how the CBA goes, but I do think you're going to see a lot of action in November, which is good for us!

JOLLY: The Cubs. The Cubs have a really big one. They might lose Seiya Suzuki and Ian Happ. They need to rebuild their rotation because Kevin Gausman and Clay Holmes are rentals. They basically got to the playoffs this year without a rotation, and without a real dignified closer in their bullpen.

They need to do a ton, because now they're at a crossroads. The Brewers, their rival, have reached an apex, and the Cubs are still kind of where they were at the beginning of their window, which is they can't really get over the hump and win a five-game playoff series. So it's a huge offseason for them to spend where other big-market teams like the Dodgers or Mets might not. They kind of need to act like they're one of these powerhouse franchises. Otherwise, I think they're going to get completely left in the Brewers’ dust for the foreseeable future.

JOLLY: It's weirdly a good free agency class for the Mets, because it's really not good for a lot of other teams. But if you need a pitcher or a second baseman, it's a good market for that, and that's kind of what the Mets need, because I don't think they're going to entertain Marcus Semien too much longer.

Everyone has them pegged as the Skubal team. It makes sense. I don't know how I feel about that, to be honest. But I do think they'll end up with one of these big three or four pitchers, a Michael King, or Freddy Peralta — which would be crazy, but maybe. Then they'd probably go get one of these second basemen: Luis Arraez, Jazz Chisholm, Gleyber Torres, or Brandon Lowe. I really prefer Brandon Lowe. It's a good spot for them to foster what they already had going in the second half and then add one or two big pieces on top. We know Bo Bichette is coming back, so that's penciled in.

So, I don’t know. If you could hear my tone, it’s not optimistic.

JOLLY: His elbow. It's always scary. He's had prior arm surgeries, which is to be expected with someone hitting free agency at age 30. I think it's also just a price-tag thing. The Mets already have massive price tags on three of their infielders, and now they'd be adding another one for a frontline starter.

But it's something they need. They need an ace at the top, and they could do other supplemental things, like bring Clay Holmes back, if that's what they want to do. But I think they're going to have to pay out big for one of these pitchers because it’s just something they need.

JOLLY: Baltimore Orioles.

JOLLY: Chicago Cubs.

JOLLY: Ah, it's such a weird one. Such a weird one. Atlanta Braves.

JOLLY: Who doesn't need a good defensive second baseman? Who doesn’t care about that? Do the Red Sox make sense? Yeah, he's a Red Sox, sure.

JOLLY: He's a New York Met. I just know it’s gonna happen. I'm not happy about it, but I know it's… yep.

JOLLY: Chicago Cubs.

JOLLY: I think he’s a New York Met. I think he's unlocked the best version of himself, but this is just the kind of signing the Mets make where they buy big on a contract year and then he's not quite the same. But if it happens, I'm happy.

JOLLY: I'm very hopeful that he is still a Pittsburgh Pirate, because that would be a good move for them.

JOLLY: Chicago White Sox.

JOLLY: Cub. I think he’s a Cub. I think they’re gonna spend a ton of money.

The 2026 season is in the books. What was your favorite moment?

The best of what came out of Jomboy HQ, the Warehouse, and anywhere else we wandered out to over the last week.