One of the best days of the MLB season is here. Playoff baseball is spread across four cities, featuring eight teams and over ten hours of intense, high-quality action. I wrapped up the regular season with some good fortune, as the Giants’ four-game win streak to close out the year gave me a perfect 4-0 record on futures bets. If you missed it, check out the article about it here. Let’s carry that same analytical approach into this year’s playoffs. This season feels more unpredictable than ever, with no teams reaching 100 wins and just seven victories separating the first and sixth seeds in the AL. Get ready for an exciting month of baseball where any team could take home the World Series.
#3 CLEVELAND GUARDIANS vs #6 DETROIT TIGERS
The Tigers completely faltered in the second half of the season. If not for a tiebreaker with Houston, their collapse would have been compared to the Mets’. Now, they face the Cleveland Guardians, who outpaced them in September, including two series wins against Detroit with a 5-1 record. Over the season, Cleveland went 8-5 against the Tigers, largely due to their pitching dominance, boasting a 2.19 ERA in 13 games. Detroit’s pitching held its own with a 2.82 ERA against Cleveland but allowed nine unearned runs in those games. This was unexpected, given the Tigers ranked in the top seven in MLB defensive stats like errors, fielding percentage, and defensive efficiency. Which may show some nerves against their hated division rivals.
The trends for these two teams are heading in opposite directions. Detroit went 7-17 in September, while Cleveland posted a strong 20-7 record. Over the past three months, Cleveland has outpaced Detroit by 14 wins. Historically, only two of the 22 wild card teams in the last four playoffs had sub-.500 records in September, both being sixth seeds (the 2022 Phillies and 2024 Royals). While both advanced past the first round, it was due to having stronger three-month records than their opponents. That’s not the case here—Detroit is in freefall, while Cleveland is on a roll.
CLEVELAND GUARDIANS GAME 1 Winner (+145)
CLEVELAND GUARDIANS SERIES Winner (-105)
#4 CHICAGO CUBS vs #5 SAN DIEGO PADRES
This is definitely the toughest series for me to predict. Most pundits are all in on the up-and-coming Cubs, and it’s easy to see why. Chicago had their best season since 2018 with 92 wins. Their success came from an offense that ranked 3rd in the NL in runs, 3rd in home runs, and 1st in OPS+. But they weren’t just about offense; their 3.79 ERA was 4th best in the NL, and defensively, they shined with the 3rd fewest errors and 3rd best fielding percentage in the majors. So, what’s not to like about the North Siders? If anything, it might be their lack of strikeout power on the mound, with the 4th lowest K rate in the majors, while 12 of the other 14 playoff teams rank in the top half of the league in that category.
But will that matter versus a Padres team that doesn’t strike out much anyway (ranking 3rd lowest K rate in MLB)? My gut says maybe. But more importantly, Chicago’s strengths are also the Padres greatest attributes. San Diego has the 3rd lowest team ERA in baseball (3.64) and lowest batting average against (0.225). However, Chicago has played well against the better staffs, posting an 18-14 record against the teams with the best batting average against.
This matchup looks like a tough battle for both teams. With no clear edge—since they went 3-3 against each other this season—I’m focusing on the emotional aspect. The Cubs haven’t made the playoffs since 2018. We’ve seen four instances where teams had as long of a drought as the Cubs. Last year the Tigers broke a nine-year playoff drought and won their opening round series against Houston. Similarly, Kansas City had an eight-year gap before winning their first-round series in Baltimore last year, Arizona ended a six-year drought in 2023, and the Phillies returned after ten years to win their opening series in 2022. The Cubs are young, hungry, and led by a coach, Craig Counsell, eager to prove himself. That’s my edge, and why I’m backing the blue in this series in Chicago.
NOTE: Game 1 starter for the Cubs, Matthew Boyd, is 12-1 at home this season. Three of the Cubs/Padres games went under 7 runs.
CUBS/PADRES Game 1 under 6.5 (+102)
CHICAGO CUBS SERIES Winner (-125)
#4 NEW YORK YANKEES vs #5 BOSTON RED SOX
When it comes to baseball rivalries, few can top the heated clash between New York and Boston. These two cities share an intense animosity that has delivered some of the most unforgettable postseason moments. From Aaron Boone’s walk-off home run to the Red Sox’s epic comeback from a 3-0 deficit, the drama is unmatched. This year promises more of the same, with plenty of firepower on both sides. The Bronx Bombers bring the league’s best offense, leading in home runs and runs scored, while Boston counters with a solid pitching staff and a versatile young offense capable of winning in various ways.
Since the MLB expanded its playoffs in 2022, the #4 seed in the AL is 0-3 in wild card series and 0-6 in wild card games. Each season, the #4 seed came from the AL East, which is an intriguing trend that tells only part of the story but holds weight in this new era. Interestingly, every #4 seed had a stronger September than their opponent, including the Yankees, who finished 18-7 in the final month. While this might be more of a negative trend than a solid fact, the season series makes me favor Boston. The Red Sox are 9-4 against the Yankees this year and have a clear edge on the mound in Game 1. Garret Crochet is 3-0 against the Yankees this season, while Yankees SP Max Fried, despite a great 2025 season, has a playoff ERA over 5.00.
BOSTON RED SOX Game 1 Winner (+115)
BOSTON RED SOX SERIES Winner (+130)
#3 LOS ANGELES DODGERS vs #6 CINCINNATI REDS
This series looks to be the biggest mismatch on paper, and the field. However, let me lay out some past trends that may make it look closer than it appears. Since expanding to 12 teams in 2022, the #6 seed in the National League is 3-0 in Wild Card series. This included some significant upsets such as Arizona over Milwaukee. But in all three cases, this was a weaker #3 seed and not the reigning World Series champs, like the Dodgers are this year. Quite honestly, Cincy shouldn’t be here. Outside of Detroit, they played the worst baseball of any playoff team after the all-star break, posting a 39-38 record since July 1st. And they only got swept once this year, and it was to the hands of the team they are facing off today.
This one is too lopsided for me. The Dodgers played some great ball down the stretch. And that was first and foremost with their pitching as they allowed a sub 0.200 batting average to opponents in September. Coincidentally, that matched the return of some of their aces (Blake Snell) and Shohei Ohtani. If you’re going to be this series, to me you just have to predict a sweep. If the Dodgers get in any trouble, it’s with their bullpen. But that might not matter as they could be up too much already for the shaky relievers to matter.