Sep 12, 2025; Miami, Florida, USA; Detroit Tigers starting pitcher Tarik Skubal (29) exits the game against the Miami Marlins during the fourth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images For better or worse, Rob Manfred has finished turning Major League Baseball’s postseason — once the shortest tournament and the one that most rewarded regular season excellence — into the most unpredictable free-for-all this side of the NCAA Tournament.
The wild-card round is particularly challenging to forecast. Think of it as the first round of the NCAA Tournament, if every first-round game was an 8 vs. 9 coin flip. The team with fewer regular season wins is 9-3 in the best-of-three wild card series since 2022.
And since this is only a four-round tournament, your entire bracket can be in tatters with one wrong pick.
In other words: Don’t blame us if these picks go sideways. Here’s our best guesses as to how the next three days will unfold.
No. 3 Cleveland Guardians (88-74) vs. No. 6 Detroit Tigers (87-75)
The Tigers appeared headed for a first-round bye and the Guardians looked ready for October tee times before Detroit went 7-17 in September while Cleveland roared to a 20-8 finish to complete their comeback from a 15 1/2-game deficit — the largest ever overcome by a division champ.
But there’s that old cliche about momentum being the next day’s starting pitcher, and Detroit’s starter today is likely repeat Cy Young Award winner Tarik Skubal. Pitching and offense win in the playoffs and the Guardians have none of the latter. Cleveland’s 643 runs scored are the third-fewest for a playoff team in a full season during the wild card era.
Plus, ending the regular season in rollicking fashion and then losing in the first round of the playoffs is the most Cleveland thing possible. It already happened in 2013 and 2017!
PREDICTION: Tigers in 2
No. 4 New York Yankees (94-68) vs. No. 5 Boston Red Sox (89-73)
Aug 23, 2025; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) pitches against the New York Aug 23, 2025; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) pitches against the New York Yankees during the first inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn ImagesYankees during the first inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images Here’s the perfect example of a pick either making or breaking a bracket. The defending AL champion Yankees went 18-7 in September and finished the season with the best run differential (plus-164) in the AL. Aaron Judge is red-hot and healthy, Giancarlo Stanton is the new Mr. October and All-Stars Max Fried and Carlos Rodon headline the rotation.
The Red Sox are missing star rookie outfielder Roman Anthony (oblique) and No. 3 starter Lucas Giolito (elbow). Closer Aroldis Chapman had a monster regular season but is synonymous with October meltdowns.
Yet…the Yankees are 23-26 against playoff teams this season and still prone to the fundamental mistakes that cost them in last year’s World Series. The Red Sox will start a true ace, Garrett Crochet, tonight. And Boston is 24-15 against the Yankees over the last three years. If the Yankees get out of this series, they’ll probably win the pennant. And yet…
PREDICTION: Red Sox in 3
No. 3 Los Angeles Dodgers (93-69) vs. No. 6 Cincinnati Reds (83-79)
Los Angeles Dodgers shortstop Mookie Betts (50) high-fives first baseman Enrique Hernandez (8) after defeating the Arizona Diamondbacks 8-0 to clinch the National League West title during the season home finale at Chase Field in Phoenix on Sept. 25, 2025. PHOTO USA TODAY SPORTS IMAGES The closest thing we’ll see this year to a seemingly lopsided 1 vs. 16 duel. The defending champion Dodgers might have life hacked their way through a blase regular season, only to arrive in the playoffs with a loaded rotation, the NL’s most potent offense and Shohei Ohtani ready to do his two-way thing on the postseason stage for the first time. The bullpen remains a question mark, but starters Tyler Glasnow, Roki Sasaki and Emmet Sheehan will all be available in relief.
The Reds “earned” the final wild card berth by stumbling just a little bit less down the stretch than the New York Mets. But Cincinnati has some giant slayer capabilities here with Hunter Greene, Zack Littell and Andrew Abbott lined up to start. And there are few managers better prepared for the postseason gauntlet than the Hall of Fame-bound Terry Francona, who came out of retirement to do what he does best — win on a budget. Don’t be surprised if Cincinnati pulls a Princeton in 1989. At least.
PREDICTION: Dodgers in 3
No. 4 Chicago Cubs (92-70) vs. No. 5 San Diego Padres (90-72)
Sep 28, 2025; Chicago, Illinois, USA; Chicago Cubs right fielder Seiya Suzuki (27) crosses home plate after hitting a solo home run against the St. Louis Cardinals during the fifth inning at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images The Cubs were .500 or better every month and never won or lost more than five straight games, which made them the steadiest team in a topsy-turvy season. But star outfielder Kyle Tucker is nowhere near 100 percent after dealing with a calf injury in September and the rotation will be missing potential Rookie of the Year Cade Horton, who suffered a broken rib last week. Likely Game 1 and Game 2 starters Matthew Boyd and Shota Imanaga posted a combined 6.00 ERA in September.
Yet the Cubs still feel like a safer bet than the ever-combustible Padres, who have a bullpen for the ages but also scored the fewest runs and produced the highest rotation ERA of any NL playoff team. San Diego is also more prone to head-scratching fundamental miscues than anyone in the field — even the Yankees. Leon Durham finally gets his revenge for 1984.
PREDICTION: Cubs in 2
