With less than two weeks remaining in the regular season, the MLB championship picture is as cloudy as it's been in recent memory. The two-time defending champion Los Angeles Dodgers are a MASH unit with a sketchy bullpen and an underachieving offense. The top seed in both leagues, the Tampa Bay Rays and Milwaukee Brewers, have very little track record of postseason success. Traditional powers like the New York Yankees, Boston Red Sox, Chicago Cubs and Philadelphia Phillies have the talent to go on a run ... and weaknesses that could bounce them early.
With so much chaos around the league, a single breakout performance could swing the chase for a World Series. And it just so happens that all 12 teams currently in the playoff bracket have at least one player who could make all the difference come October.
Tampa Bay Rays: OF Victor Mesa Jr.
All year long, the Rays have been desperate for one more bat to emerge alongside Junior Caminero, Yandy Diaz and Jonathan Aranda — preferably in the outfield, where the team's gotten very little from the likes of Cedric Mullins, Jonny DeLuca and Chandler Simpson. And then, all of a sudden, Mesa Jr. — a 25-year-old non-prospect who struggled mightily in his first taste of MLB action last year — started hitting like an MVP candidate, with a 1.300 OPS so far in September.
To what extent is that at all sustainable? The answer to that question may determine Tampa's offensive ceiling — and how far they can go in the AL playoffs.
Chicago White Sox: LHP Hagen Smith
At what point do the White Sox just throw caution to the wind and let Smith start Game 1 of a playoff series? Chicago's top pitching prospect hasn't been fully stretched out at the big-league level, but he's been sensational in shorter stints, with a 0.41 ERA and a 13.1 K/9 since being promoted. Anthony Kay, Sean Burke and Davis Martin have all turned into pumpkins simultaneously, and the deadline acquisition of Luis Castillo has proven to be a disaster. The White Sox aren't going anywhere in October if they can't find more reliable rotation options, and at this point, Smith might be the best bet despite being a rookie with 22 innings under his belt.
Houston Astros: OF Cam Smith
The physical tools have never been in question for Smith, who brings an intoxicating blend of power, speed and overall athleticism. Whether he can actually hit is the real issue: Sometimes he looks like a future MVP candidate, while at others he looks totally lost. He's slugging .513 since the beginning of August, but that mark has come with an OBP well south of .300, a steep price to pay for that pop. Can Smith finally become the guy the Astros thought they were getting when they made him the return for Kyle Tucker last offseason? If not, Houston might not have enough offense to make it through October, as even Yordan Alvarez has been scuffling lately.
New York Yankees: Jazz Chisholm Jr.
We know the Yankees are going to be able to pitch; this is quite possibly the best rotation in baseball, and while the bullpen doesn't inspire as much confidence, the trio of David Bednar, Brent Headrick and Paul Blackburn has been good enough so far. Whether New York can make it back to the Fall Classic will largely come down to whether they can score enough runs — and getting the 2025 version of Chisholm Jr. at the plate would go a long way toward accomplishing that goal.
It's hard to overstate the difference Chisholm Jr. makes for this lineup when he's right. But he hasn't been right pretty much all year, and now he's on the IL with a thumb sprain. If he can't make it back for October, or if the layoff throws his swing out of whack, that puts a ton of pressure on deadline additions Luis Garcia Jr. and Heliot Ramos and rookies Spencer Jones and George Lombard Jr. to provide lineup depth behind Aaron Judge and Ben Rice. Not the situation the Yankees want to be in.
Boston Red Sox: LHP Garrett Crochet
At this point, it seems all but certain that Crochet won't be returning to Boston's rotation this year, as there simply isn't enough time left in the regular season for him to build up to a starter's workload. But he threw another bullpen at Fenway Park on Tuesday, inching closer to a return that could revamp the Red Sox pitching staff all the same.
Even without Crochet, Boston has enough rotation options in Sonny Gray, Ranger Suarez, Payton Tolle, Jake Bennett and Co. Even getting Crochet for a couple of innings at a time could be a game-changer in building a bridge between those guys and the back end of the bullpen, papering over a real weakness on this roster — and taking some pressure off of an offense that's been hard to rely on all year.
Cleveland Guardians: OF Chase DeLauter
Once again, the Guardians near October wondering how they can put enough offense around Jose Ramirez to win games in October. DeLauter could well be the answer, as he's been a true force in the middle of this Cleveland lineup when healthy. Unfortunately, being healthy has been something of an issue throughout 2026 and his pro career at large, and sure enough, word broke on Tuesday that he's experiencing wrist discomfort.
We don't yet know the extent of the issue, or whether it will cost him any time. But if he's not right come playoff time, it's hard to imagine Jo Adell, Travis Bazzana and Co. to produce enough against the best pitching in the league.
Milwaukee Brewers: LHP Kyle Harrison
Not too long ago, it looked like Milwaukee would enter the postseason with one of the best starting trios around in Jacob Misiorowski, Logan Henderson and Harrison. But the former Giants and Red Sox lefty has come unraveled ever since his elbow started barking back in July, so much so that the Brewers shifted him to a bullpen role this week — only to watch him promptly give up four runs on four hits without recording a single out against the Reds.
With the first-half version of Harrison, this team would be very, very tough to beat. Without him, though, they're down to two reliable starters, neither of whom have all that much big-game experience.
Los Angeles Dodgers: RHP Edwin Diaz
Diaz's current rehab stint isn't going any better than his time in the Majors this year, as the righty has allowed 10 earned runs across just 5.2 innings in Triple-A. The Dodgers would love to be able to add one more high-leverage arm to the back of their bullpen to give Tanner Scott some help, but it's hard to imagine Diaz being trusted with postseason innings with the way he's been throwing the ball all season.
There's still a chance that he can find his old form, but his stuff has been down across the board, and it's unlikely that there's a switch just waiting to be flipped. Which would leave Los Angeles' relief corps in a pretty precarious place, no matter how much rotation firepower they have at their disposal.
Atlanta Braves: OF Michael Harris II
Arguably no player in all of baseball blows hot and cold like Harris II, who can look like an MVP candidate for weeks at a time and then completely lose his sense of the strike zone. He's at the latter point right now, and has been all September long — a big reason why the Braves offense has gone into the tank of late.
Atlanta's question marks in the rotation have been well-documented. But no matter what the Braves get from guys like Tyler Mahle and AJ Smith-Shawver come October, this team is going to need its lineup in vintage form to get past the beasts of the NL. Harris II is an integral part of that equation, especially with Austin Riley mired in a season-long funk.
Chicago Cubs: RHP Kevin Gausman
It's a simple proposition for the Cubs: If their pitching shows up, their lineup is good enough to beat just about anybody in a short series. Shota Imanaga has started to figure it out again of late, while Clay Holmes has been everything the team hoped for when it acquired him at the trade deadline. But who do you trust to start Game 3 if the postseason began today?
Chicago also brought in Gausman at the deadline hoping he'd be the answer to that question. It hasn't happened yet, though, with a 5.31 ERA across seven starts with the Cubs. If Gausman can't revert back to something close to his 2025 self, the job will fall to the likes of Matthew Boyd or David Peterson — which is not something that should inspire a ton of confidence.
Philadelphia Phillies: RHP Andrew Painter
Painter would've been the answer here anyway, but Jesus Luzardo landing on the IL with a shoulder issue just makes him even more critical to Philly's postseason hopes. At this point, the Phillies lineup is what it is: Kyle Schwarber and Bryce Harper are the only two regulars with an OPS above league average. This team is going to have to pitch its way to success in October, and with Luzardo potentially out of the equation, that means Painter is going to have to step up.
The good news is that he's really come on after returning from a midseason demotion, finally blossoming into the guy who was once the best pitching prospect in the sport. The bad news is that he's yet to start a postseason game, and that's a lot to ask of any 23-year-old. Even with Cristopher Sanchez and Zack Wheeler at the top, you can't survive multiple playoff rounds with just two reliable starters.
San Diego Padres: RHP Nick Pivetta
San Diego's big bats have finally emerged from their season-long slumber, a big reason why the Padres have surged into firm control of a Wild Card spot. But for as good as Fernando Tatis Jr., Jackson Merrill and Manny Machado can be, and for as devastating as this bullpen looks in a playoff setting, you still need some starting pitching if you want to reach the World Series.
Right now, that's a huge question mark for the Padres, who don't have much of anything reliable beyond Michael King. All due respect to Walker Buehler and Randy Vasquez, Pivetta is the most likely shot, as he's looked pretty good in two starts since coming back after five months on the IL. San Diego will need him to be 2025 Nick Pivetta to get past L.A., Milwaukee or Chicago.
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