October is the month that makes or breaks legacies, and that's just as true of managers as it is of the players themselves. In a short series, and with the chance at a World Series title on the line, every decision takes on outsized importance, and just one false step in lineup construction or bullpen management can send you home for a long, cold offseason.
A few managers have already learned that lesson the hard way this month, as the Wild Card round has come and gone and the NLDS and ALDS are underway. But eliminated skippers are hardly the only ones that have been exposed on the playoff stage. Here are four managers who have had their flaws laid bare for all to see, and how they can earn back fans' trust moving forward.
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4. Mike Shildt, San Diego Padres
Shildt isn't the biggest reason the Padres' all-in gambit fell flat in a Wild Card loss to the Chicago Cubs last week. He's not why Fernando Tatis Jr. and Manny Machado failed to hit like superstars, and he's not why San Diego had no other choice but to turn to 39-year-old Yu Darvish in a winner-take-all Game 3. For all of AJ Preller's wheeling and dealing at the trade deadline, this was a roster that entered October with obvious holes, and those holes were bound to be exploited no matter who was in the dugout.
But man, Shildt sure didn't help matters very much. Tatis Jr., Machado and Jackson Merrill not living up to their pedigrees is one thing; continuing to hit Luis Arraez in the No. 2 hole is quite another, and certainly contributed to just how mightily the top of the Padres' order struggled at Wrigley Field. It's also unclear exactly why Shildt decided to use righty Michael King for a grand total of one inning across three games despite King looking like one of the best pitchers on San Diego's roster.
Again, Shildt wasn't what sunk the Padres. But he is a manager who has a tendency to be awfully set in his ways, and while that formulaic approach works well when you've got the horses, this roster demanded a bit more creativity. We'll see if he's got that in his bag in 2026.
3. Alex Cora, Boston Red Sox
Cora entered Boston's AL Wild Card showdown against the rival New York Yankees with a reputation for absolutely owning counterpart Aaron Boone, especially in the playoffs. He exited three days later with that reputation in tatters, and some very difficult questions to answer.
Everybody was quick to praise Cora after the Red Sox' win in Game 1, but really, that had more to do with Garrett Crochet than anything else — managing becomes a whole lot easier when one of the best pitchers in the sport looks downright untouchable for eight innings. And from there, Cora made one head-scratching decision after another across the next two games, from leaving Garrett Whitlock out to dry in the eighth inning of Game 2 to leaving Connelly Early out to dry in the fourth inning of Game 3.
Getting flatly outmanaged by Boone in the postseason is ... not a great look, to put it mildly. Of course, Cora has a World Series ring to fall back on, and he did a nice job of navigating what was an awfully tumultuous season in Boston. He also had a hand in that tumult, at least where Rafael Devers is concerned, and how he handles a young clubhouse in flux entering next season will be fascinating to watch.
2. Rob Thomson, Philadelphia Phillies
The Phillies' postseason run is exactly one game old, and already fans are ready to run Thomson into the Delaware River. Sure, it would've helped it Philly's offense managed to do anything at all beyond the second inning, but when you take a 3-0 lead into the sixth, you expect to win that game. And yet, once again, the Phils managed to let a home playoff game slip away, and Thomson's in-game decisions bear a lot of the blame.
Leaving Cristopher Sanchez in to face the top of the Dodgers' order a third time was understandable enough, given just how dominant the lefty had been to that point. Once he delivered a two-out walk to Freddie Freeman, though, Thomson should have immediately gone to the bullpen for a right-handed option. (L.A.'s next two batters, Tommy Edman and Enrique Hernandez, are both far more effective against lefties than righties.) Instead, Thomson stuck with Sanchez to disastrous results: Edman singled, then Hernandez followed with a double to cut the Philly lead to 3-2.
The seventh inning was arguably even worse. Despite knowing that he'd want a lefty on the mound to face Shohei Ohtani, who was batting third in the frame, Thomson elected to start the inning with righty David Robertson. Robertson promptly allowed both Andy Pages and Will Smith to reach base, meaning that left-hander Matt Strahm had to not only face Ohtani but then face two dangerous right-handed hitters — Mookie Betts and Teoscar Hernandez — to escape the jam. STrahm did manage to strike out Ohtani, but the rest went about as you'd expect.
Why not just start the inning with Strahm? Sure, in a perfect world, Robertson gets the first two outs of the inning and allows Strahm to face Ohtani in order to end the frame, allowing you to start the eighth with a new pitcher to face the heart of L.A.'s lineup. But that was a huge gamble, when Thomson instead could have just brought Strahm in to start the inning and had him deal with Pages and an injured Smith — hitters far less liable to do damage.
This is hardly a one-time occurrence with Thomson. His bullpen management has driven Phillies fans nuts for years now, as has his stubborn deference to his veteran hitters. If Philly wants to knock out the defending champs, they're going to need their manager to maximize the talent they have on hand, and Thomson simply isn't doing that right now. He's a fine regular-season manager, but when the lights are brightest and every decision looms large, he needs to show that he can think these things through and outfox Dave Roberts.
1. Craig Counsell, Chicago Cubs
Well, Chicago, don't say that Milwaukee Brewers fans didn't try to warn you.
Craig Counsell probably wasn't the one who actually made the decision to ride with Matthew Boyd on three days' rest in Game 1 of the NLDS on Saturday, and there's not a ton that you can do when your pitching staff collapses immediately in the way that the Cubs did over the first couple of innings of a 9-3 loss. Jed Hoyer should shoulder plenty of the blame here for putting his roster in a bind with a shockingly passive trade deadline.
Still, it's probably not a coincidence that this is yet another instance in a career full of them in which Counsell has gotten immediately pantsed in the postseason. Just hours after saying that the Brewers "don't swing" under manager (and Counsell's former bench coach) Pat Murphy, Milwaukee was jumping on Chicago pitching as early as humanly possible en route to an offensive outburst that put the game away almost as soon as it began.
Maybe it's strategy, maybe it's small sample size, maybe it's vibes; but whatever the case, Counsell consistently comes up small on the biggest stages, and his demeanor doesn't exactly inspire confidence that things will turn around moving forward. A little more urgency, and a little more fire, would do wonders to at least humor this fan base, and it would also help if he could find a way to get one over on his former team the way they've done against him consistently.