My 2026 MLB Playoff Picks, Starting With the Least Exciting Take in Baseball

A Brewers game at American Family Field, then called Miller Park, in 2016. Photo: redlegsfan21, Wikimedia Commons, CC BY-SA 2.0

I’m about to do the least fun thing a person can do in October, which is pick the one seeds. I know. I’ll explain myself at the end.

First, a quick shout out to my second favorite team. The Milwaukee Brewers won 103 games this year, a franchise record, and finished with the best record in baseball. They’re also just a super fun team to watch. Jacob Misiorowski throws a baseball the way most people wish they could throw anything, and this group plays like it enjoys being there. It was an incredible season, and I just like to see that.

Now the actual baseball. All four Wild Card series start today, they’re all best-of-three, and I’ve got a pick for each.

Phillies at Braves

The Phillies squeaked into the playoffs, and it got very hairy near the end. They needed to win Game 162 to clinch, Zack Wheeler had to start that finale to get them there, and their bullpen posted a 5.79 ERA in September, worst in the majors. Now they open on the road against a division rival that beat them in nine of 13 meetings this year.

And that division rival is handing the ball to Chris Sale. At 37 years old, Sale went 14-9 with a 2.16 ERA and struck out 200 hitters in 162 2/3 innings. The Braves spent all summer giving him extra rest specifically so he’d be fresh for this. I think Sale is going to pitch amazing, and I think the Braves take the series.

Pick: Braves

White Sox at Astros

I love that the White Sox are here at all. They lost 102 games last year and made the playoffs this year. That’s a genuinely great story.

It’s also a team that strikes out a ton. Chicago whiffed on 27.5 percent of its swings this season, and shortstop Colson Montgomery set the single-season major league record with 227 strikeouts. Montgomery also hit 31 home runs, so it isn’t all bad, but in a short series against pitchers who miss bats (Josh Hader was 26 for 26 in save chances), that strikeout rate is going to hurt. Houston, meanwhile, hit 226 homers. I think the Astros just hit bombs against this White Sox team and move on.

(Fun fact: the Astros went 81-81, the worst winning percentage for a division winner in MLB history. They’ll be hosting a playoff series anyway. Baseball is great.)

Pick: Astros

Red Sox at Yankees

You want to talk about my eyes being glued to baseball? This is the one. Red Sox and Yankees, all three games in the Bronx, in October. It’s going to be fantastic.

Full disclosure: I’m a little bit of a Yankees hater. I do think they’re a good team, though, and I don’t even mind a lot of the individual guys. Cam Schlittler is fun to root for. He leaves it all out there, on the mound and on social media, and he just had a monster year (1.95 ERA, 239 strikeouts). The best part is he grew up a Red Sox fan, then ended Boston’s season in this exact round last year with eight shutout innings. Aaron Judge is a Team USA guy, and I don’t mind him either. (He’s also dealing with a calf strain, and the Yankees have been preparing as if he won’t play this series, which matters a lot.)

But I think we could see some serious magic out of this Red Sox team. Boston was 14 games under .500 in late June and clawed all the way back into the field. A team that climbs out of a hole like that already has a little magic in it.

Pick: Red Sox

Cubs at Padres

This is the most even series of the four, for sure. The Cubs won five of the six regular-season meetings and have the better offense. The Padres went 51-30 at home and have the best bullpen in the field.

It’s a coin flip, but I’m going to go with the Padres. Mason Miller finished with 38 saves and a 1.67 ERA, Adrian Morejon and Bradgley Rodriguez get him the ball, and the Cubs don’t really have a set closer. I just think San Diego’s bullpen is good enough to get them through, and that they rally in the late innings when it matters.

Pick: Padres

Every One of These Could Go Either Way

I lean Braves, Astros, Red Sox and Padres, and I’d be lying if I said I felt great about any of them.

That’s the nature of a best-of-three. If a series goes two games, your best hitter gets something like eight or ten at-bats. If it goes three, maybe 15, max. That’s the whole sample. There’s a world where the best bat on either roster goes 1 for 15 and his team is headed home before the weekend. I wouldn’t bet on it for any particular guy, but it happens every year to somebody. Things can flip either way in a hurry.

The Rest of the Bracket

I’ll come back with a real breakdown of the Division Series once these Wild Card games are done. But since I’m already on the record, here’s where I have everything landing.

Division Series

• Brewers over Padres
• Dodgers over Braves
• Rays over Red Sox
• Astros over Guardians

League Championship Series

• Brewers over Dodgers
• Rays over Astros

World Series

• Brewers over Rays

The Dodgers are going for a three-peat, and I have them running into Milwaukee a round short. On the other side, Tampa Bay went 98-64, went 55-26 at home, and gets home field in the Division Series. Somebody in Boston is going to be mad at me about Rays over Red Sox, and that’s fine.

So yes, that’s a Brewers-Rays World Series with Milwaukee winning it all. I know it’s not sexy to pick the one seeds. But those have been the two best teams in baseball this year, and I’m not going to pretend I don’t see it.