MLB Wild Card Series Picks: Rematches and “The Rivalry” Renewed

October baseball: is there anything like it in sports? That is actually a rhetorical question, because of course there isn’t.

We start with the “mini” series version, a best-of-three-all-in-one-place wild card series, and we have two juicy divisional rivalries to go along with a rematch from last year and a series featuring a blue blood vs. a team that made history coming this far from the depths of despair.

So without further ado, let’s dive in:

NLDS

(5) Cubs at (4) Padres

A rematch, but this time in the beautiful weather of San Diego. The Padres got hot down the stretch, winning 17 of their final 20 games to earn homefield advantage. The question for the Padres is whether they can get enough offense and starting pitching. The question for the Cubs is which version of this ever-streaky club shows up? If necessary, can PCA single-handedly put the Cubs on his back in October?

Defense was huge for the Cubs in winning last year, two games to one. The Padres have a speed element now, finishing tied for second in stolen bases, and of course the edge in terms of bullpen. The starters ERA has been worse than the Cubs, however, and the Cubs have the league’s highest OPS against left-handed pitching, which could give them a slight boost against elite Padres setup man Adrian Morejon.

I am so very tempted to take the Cubs, because I can’t shake this feeling that PCA has at least one big October moment in him. San Diego has continually fallen short in October, and the veteran, winning experience that the Cubs have with players like Alex Bregman, Dansby Swanson, Kevin Gausman, and Clay Holmes makes me believe they can overcome the San Diego bullpen and eke out a series win. But the Padres are hot and look like the slightly “safer” choice, so I’ll (perhaps begrudgingly) go with them. Pick: Padres in 3.

(6) Phillies at (3) Braves

The Braves owe the Phillies, don’t they? Despite winning 100+ games and the NL East crown in both 2022 and 2023, the Phillies knocked Atlanta out of the ALDS in four games both times. Now, Atlanta gets a shot at revenge against a team that truly limped down the stretch and will likely not be able to deploy Zack Wheeler after he pitched the final day of the season.

The Braves have big starting pitching concerns of their own, but in a short series, they can throw Chris Sale in Game 1 and hope that if he pitches like he has all year, they can get enough from Tyler Mahle and Grant Holmes (if necessary) to finish off the series. The offense has gone stagnant for Philadelphia, and there’s reason to believe it will continue to struggle despite a strong final day of the season. That is what gives me just enough confidence to take the home team here. Pick: Braves in 3.

ALDS

(5) Red Sox at (4) Yankees

Here we go again. For the seventh time this century, the bitter AL East rivals will go head-to-head in October. So far it’s been split, each team winning thrice. The Red Sox had won three straight until Cam Schlittler brought the hammer down in Game 3 last year, starting what’s been a dominant run for the Boston native against his childhood team. Now, it’ll be Schlittler to kick things off against young Payton Tolle.

The Red Sox won Game 1 last year, but then scored just one run the next two games to lose the series. Offense is a major concern again, even as Willson Contreras is expected to play. But will Aaron Judge? And even if he doesn’t, will that really hamper the Yankees given that they’ve played half the season without him?

One seemingly advantageous area for Boston is that it will throw two lefties (if it goes to Game 3) against a lefty-heavy Yankees lineup. But there is just too much starting pitching for New York, and the bullpen edge may go to New York as well. A Boston lineup that was among the least productive in September is also cause for concern, so here’s thinking 2026 will mirror 2025. Pick: Yankees in 3.

(6) White Sox at (3) Astros

It would be the Astros to be the first .500 or less team to make the playoffs, wouldn’t it? After all, in the shortened 2020, they went 29-31 and ended up one win away from the World Series. And now they enter the postseason with some momentum and, of course, experience, against one of the great all-time turnaround stories in the ChiSox. No team had ever made the playoffs after consecutive 100-loss seasons, which should easily cement Will Venable as the 2026 AL Manager of the Year.

But the pitching staffs for both teams are questionable, especially the White Sox, who lack an ace like Houston’s Hunter Brown. It is looking like, in essence, three bullpen games for Chicago, which is incredibly dicey against an Astros lineup that, despite their average record, led the majors in home runs with 226.

Houston has a major edge at the back of the bullpen with Josh Hader closing out games, and its experience and power should be enough to advance to the ALDS. Pick: Astros in 3.