It’s only September 29, but spiritually, October begins today.

After 27 weeks, and 2,429 games, the 2026 MLB regular season is in the books. A whole new season begins this afternoon.

With the Postseason beginning at 2 p.m. ET, we’ve tapped none other than Jolly Olive to walk us through what he’s keeping an eye on, who might surprise everyone, and the one team he sees raising the Commissioner’s Trophy in about a month’s time.

Jolly: That is a great club. I had a couple creators say that Rizo was their favorite office visit we've ever had. We've had Bill Hader here, Rob Lowe, Sal Vulcano. So I think I'm inclined to say Rizo just because he was the first guest we ever had that was asking to take pictures with our creators, which I thought was really fun. Meanwhile, he's been on TV for essentially a year straight now.

It was just really cool. He was our age, so he had our sense of humor, loves baseball, and definitely lived up to his Survivor persona.

Jolly: Rob knows ball. I wasn't going to try and set him up for failure, you know, because that'd be a rude thing to do. But I will say, especially when he was talking about, like, the old Big Red Machine from when he was growing up in Cincinnati and stuff like that, I was very thoroughly impressed. It makes sense. You know, if you're a Jomboy fan, to an extent, you’ve got to be a ball knower in some capacity. And Rob Lowe certainly is.

Jolly: I am disgusted with the White Sox-Astros bullpen game in Game 1, and I think the dichotomy of seeing those two teams play and then seeing the Yankees and Red Sox play right after will be jarring. 

Also, I was not surprised, I guess, at the muted celebration of the Phillies, because you almost stumble out of a playoff spot and then you make it in on the last day. What is there really to celebrate? Curious to see how they look because they looked dead for a while. 

And then I am sad that the Padres and Cubs have to play again because I feel the same way about them as I do Yankees-Sox: I think whoever wins that series might just win the pennant, and it sucks that one of those teams might only play two games. That's upsetting to me, for sure.

Jolly: Neither of those teams are the Dodgers, and obviously we'll come back to this in three weeks and it'll be the Dodgers, which is very funny. But I just think the Cubs are better than they were last year and I really liked them last year. Their one weakness was piecing together pitching and they figured out how to do that. They have the best defense of any team, and I think that really matters in the playoffs. 

But what's even better than being the best unit is being the hottest team — and the Padres are the hottest team. They've won, like, 20 of their last 25 home games? And they're gonna have home field advantage in this Wild Card series. I just think those two teams have full heads of steam, and the teams in front of them — the Brewers, I can't really trust, and the Dodgers who have to show some sort of weakness soon, right?

I just feel like their path will have them battle tested enough to win the World Series against whoever comes out of the AL.

Jolly: I think it's definitely that one. It's two teams that I really like. It's two fan bases that I really like. It sucks that one of them is going to go home so soon because I think if they were on different sides of the bracket, they both advance. But that is not the simulation we got. 

And I just think those two teams — I mean, listen, I could be wrong. They could get swept in the DS by the only 100-win team this year, which would make perfect sense. I just don't think that's going to happen. I think one of them is going to win the pennant.

Jolly: We just got news that Crochet is active and Judge is not, which means that I think the Red Sox are gonna lefty the Yankees to death, between Crochet and Erik Miller and Aroldis Chapman and Payton Tolle and Ranger Suárez. They can just stack these southpaws and I really worry about the Yankees. 

And the other thing I'll say, I'm going to get nerdy here just because it's something I saw recently, and it did open my eyes. Let me pull it up so I get it correct. The Yankees, of the contending teams, have, by far and away, the worst OPS as a team against starters who have an above-average Stuff+. And if you don't know what that means, it's okay: Stuff+ basically measures how nasty a pitcher is and how efficient their pitch mix is. The Rays are the best team with a .723 team mark against good pitching, essentially. The Yankees are the worst at .633. 

I've heard from my bosses for many years that the Yankees stack their big offensive days against bad pitching and it skews their numbers. And in the playoffs, you don't face bad pitching! You're going to face really good pitching and you're going to face really good left-handed pitching. So I'm very curious to see what the Yankees offense looks like. I know they can pitch, and if they get past this series, they will pitch their way to the World Series.

I do think the AL is going to be won by whoever wins this measly little three-game set.

Jolly: I think Chase Meidroth is really good. I think he's the best second baseman in the AL, and I still remember on Opening Day when he hit a home run off Misiorowski, and I was like, wow, this guy might be the real deal. He had a really, really good season. I just think the White Sox outside of Murakami and Montgomery need someone else to step up. And I think it might be him. I think he might be a big-game player. So I'm going to keep my eye on them today.

Jolly: They've gotten some pitcher injuries, but they kind of have that every year. So I won't say that. I really think they'll run the Braves in the DS. I don't think the Braves have the pitching to win that series. They would have to slug their way out of it. And I think the Dodgers have a better lineup than anybody. I think if the Padres or Cubs don’t beat the Dodgers in the NLCS, you're gonna see the three-peat.

Jolly: You saw my bracket, and I'm going to stick with it. I mean, I was going into that bracket thinking that Judge was active. I believed his words, and I was wrong. But it's really just interchangeable between Yankees and Red Sox. I just think whoever wins that series will win the AL. 

So I'll stick with the Yankees coming out of the AL. I think the Padres come out of the NL because they're just the hottest team right now. And I think if the Padres are going to make it out of the NL, they have to beat the Dodgers and once they do that, they're not going to lose the World Series. So I’m going with Padres over Yankees in six.

Jolly: I like this playoff format. I wish it didn't fall this way because I think when the right teams are in the right spots, this format is perfect. 

And I'm sad that I think they're gonna probably add more playoff teams, because we just got our first .500 team in the playoffs in a full season, which is disgusting. And that's not even because of the format — they just won their division. So, I do think realignment's probably going to be good for all this, but I like this playoff format. I'm sad that it's probably going to be the last one we get.

We know who Jolly’s breakout candidate is. What about the rest of the bunch?

Who’s a dark horse to have a huge Postseason moment?

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