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David Schoenfield
It’s still early in the postseason, but it’s never too soon to start to dream about some of the possible World Series matchups we could get later in October.
With eight teams left, there are 16 possible Fall Classic scenarios — a matchup for seemingly every type of fan to enjoy. Well, unless you were really hoping for that Colorado Rockies–Chicago White Sox or Pittsburgh Pirates–Los Angeles Angels World Series. If that’s the case, you probably need to rethink your dreams.
Here are eight of the most exciting potential matchups — one of which a majority of fans might strongly disagree with including. There is something for everyone, from history to star power to longstanding droughts. Let’s get to it.
If you like No. 1 seeds making it: Blue Jays vs. Brewers
The Toronto Blue Jays and Milwaukee Brewers were together in the AL East from 1977 through 1993, when the Brewers moved to the AL Central (and then to the National League in 1998).
The only year they finished 1-2 was 1992, when the Blue Jays won the division title by four games. The Brewers went 15-2 at one stretch in September to close the gap to two games with two games left to play, but they lost both while the Blue Jays won theirs. The franchises have had a limited trade history, although former longtime Brewers general manager Doug Melvin (still a front office adviser for the club) is an Ontario native and member of the Canadian Baseball Hall of Fame.
Five players to fill out your Immaculate Grid: Paul Molitor, Lyle Overbay, Buck Martinez, Roy Howell, Matt Stairs
Combined years without a championship: 75
Why this would be fun: Both teams finished with the best record in their league — well, the Jays tied with the New York Yankees but won the tiebreaker to get the top seed — and since the wild-card era began in 1995, the nature of baseball’s postseason makes it rare for the top seeds to meet in the World Series. It has happened just five times:
If you’re a traditionalist and want the most deserving teams to make it, this is the matchup for you. Even if you’re not impressed with Toronto’s run differential (third best in the American League), the Jays have been excellent since late May. Since May 27, they had the second-best record in the majors — behind just the Brewers.
Best potential drama: Blue Jays’ defense versus Brewers’ defense. These are two of the best defensive teams in the majors, a key reason they ended up with top records. The Blue Jays are led by infielder Ernie Clement, who tied for the MLB lead with 22 defensive runs saved while having started at all four infield positions; second baseman Andres Gimenez, who is playing shortstop with Bo Bichette injured; and center fielders Daulton Varsho and Myles Straw, who combined for 25 DRS. The Brewers are solid across the board and loaded with speed in the outfield with Jackson Chourio (whose status for Game 2 is uncertain after an MRI on his right hamstring came back inconclusive), Blake Perkins and Sal Frelick.
If you like left-handed pitching: Yankees vs. Phillies
The Yankees last won the World Series in 2009 — when they beat the Philadelphia Phillies, who were trying to defend the title they won in 2008, the last time they won it all. The Yankees took the 2009 title in six games with Hideki Matsui hitting .615 (8-for-13) with three home runs and eight RBIs to win MVP honors. The teams also met in the 1950 World Series, when the Phillies’ “Whiz Kids” were the surprise pennant winners in the National League. The Yankees swept in four games.
The obvious current tie-in is Phillies manager Rob Thomson, who served as third-base coach and bench coach with the Yankees from 2008 to 2017 before joining the Phillies as their bench coach in 2018 after the Yankees hired Aaron Boone over Thomson to replace Joe Girardi as manager.
Five players to fill our Immaculate Grid: Bobby Abreu, Oscar Gamble, Kenny Lofton, Andrew McCutchen, Charlie Hayes
Combined years without a championship: 33
Why this would be fun: Lefty pitching against lefty power. The Yankees feature lefties Max Fried and Carlos Rodon, who combined for 37 wins in the regular season, while the Phillies run out Cristopher Sanchez, Jesus Luzardo and Ranger Suarez. The last team to win the World Series with at least four games started by lefties was Atlanta in 2021, but two of those were openers. The Boston Red Sox had three southpaw starters when they won in 2018 (Chris Sale, David Price and Eduardo Rodriguez), as did the Dodgers when they lost in 2017 (Clayton Kershaw, Rich Hill and Alex Wood), but prior to the Red Sox, the last team to win with three lefty starters was the 1996 Yankees with Andy Pettitte, Jimmy Key and Kenny Rogers.
What would make this an intriguing World Series, however, is the left-on-left matchups. The Yankees have righty slugger Aaron Judge but also led the majors in home runs by left-handed batters, while the Phillies, with left-handers Kyle Schwarber and Bryce Harper, ranked fourth. The Yankees’ splits were even, but Boone did bench lefties Jazz Chisholm Jr., Ben Rice and Ryan McMahon against lefty Garrett Crochet in favor of right-handed hitters.
Best potential drama: Judge! Giancarlo Stanton! Schwarber! Harper! If those names don’t get you excited, go watch pickleball.
If you like a never-before-seen historical matchup: Tigers vs. Dodgers
Of the 16 original franchises that existed when the American League formed in 1901, there have been 44 out of a possible 64 World Series matchups (including franchise relocations). This is the most surprising one not to have occurred because the Dodgers have played in 22 World Series and the Detroit Tigers in 11. Tigers-Phillies would be the other original 16 matchup that could be crossed off this year.
Five players to fill out your Immaculate Grid: Kirk Gibson, Max Scherzer, Gary Sheffield, Enos Cabell, John Shelby
Combined years without a championship: 41 … that’s 41 for the Tigers and zero for the Dodgers
Why this would be fun: You think the Dodgers might like revenge on A.J. Hinch, Houston’s manager in 2017 when the trash-can-banging Astros beat L.A. in seven games to win the World Series? Yeah, most of the guys from that matchup are gone, but Clayton Kershaw is still here, as is L.A. manager Dave Roberts. And though the Dodgers have won two World Series since then, you know they think they were wronged in 2017.
Aside from that, we would get two classic franchises, two classic uniforms, maybe one last World Series appearance from the retiring Kershaw and the chance for the Dodgers to become the first repeat champions since the 2000 Yankees.
Best potential drama: Tarik Skubal versus Shohei Ohtani. The best pitcher in the AL versus the best player in the world. If the baseball gods are in an especially compassionate mood, they will give us Skubal starting against Ohtani. May the baddest man on the planet win.
If you like a drought-buster World Series: Mariners vs. Brewers
You want history? We have history. The Brewers were born in 1969 as the Seattle Pilots, but the Pilots went bankrupt before the start of the 1970 season and a Bud Selig-led group purchased the team (whose equipment trucks were literally stranded in Utah after leaving spring training waiting on where to go). Indeed, the Brewers’ blue and gold colors are a remnant of the Pilots’ original colors.
The Seattle Mariners came aboard as an expansion franchise in 1977 after the City of Seattle and King County sued the AL for breach of contract. In the late 1980s and early 1990s, the teams had a heated rivalry that led to a massive brawl at the Kingdome in 1990. Lately, they have been frequent trade partners. Brewers ace Freddy Peralta came over from the Mariners as a minor leaguer in exchange for Adam Lind, one of Jerry Dipoto’s first trades as Mariners GM.
Five players to fill out your Immaculate Grid: Gorman Thomas, Chris Bosio, Richie Sexson, Mike Cameron, Yuniesky Betancourt
Combined years without a championship: 104
Why this would be fun: First off, this is the matchup that gives us the longest combined title drought, with neither franchise having won a World Series (at least Milwaukee has the Braves, who won in 1957, but even that was 68 years ago). The Pilots tie-in is certainly interesting, but mostly this is fun because you can make the argument that the biggest story in the AL this season was Cal Raleigh bashing 60 home runs and the Mariners winning 17 of 18 in September to capture their first division title since 2001, and that the biggest story in the NL was the Brewers finishing with the best record in the majors, winning more games than the superstar-laden Phillies or Dodgers.
The contrast in styles would be intriguing as well. The Mariners — despite playing in a pitcher’s park — finished third in the majors in home runs. It wasn’t just Raleigh, as Eugenio Suarez hit 49 (between the Diamondbacks and Mariners) while Julio Rodriguez (32), Randy Arozarena (27) and Jorge Polanco (26) each topped 25. The Brewers were second in the majors in batting average and stolen bases while ranking fourth in lowest strikeout rate. Don’t, however, view the Mariners as a one-dimensional team: Though they can’t match Milwaukee’s speed up and down the lineup, they did finish third in the majors in stolen bases as Arozarena, Rodriguez and Josh Naylor each swiped at least 30 bags.
Best potential drama: Mariners hitters versus late-game heat. Unsurprisingly, considering his 60 blasts, Raleigh led the majors with 34 home runs against fastballs, and improving against four-seamers up in the zone was a key to his big season. But the Brewers’ bullpen can really dial it up. Abner Uribe throws a 99 mph sinker. Trevor Megill throws 99 mph. Jacob Misiorowski, if he’s in the pen and not starting, throws 99 and reaches triple digits. Aaron Ashby is a lefty with 97 mph gas. Nick Mears sits at 95 with a wipeout slider.
If you like cold weather: Tigers vs. Cubs
These teams have met in four World Series — although the last one was 80 years ago. The Chicago Cubs won in 1907 and 1908, defeating the Ty Cobb-led Tigers. Detroit won in 1935 and 1945. Aside from that, this would give us another original 16 matchup, and those always seem a little special. As long as these two teams have been around, they haven’t had much intertwining history. They didn’t even make a trade with each other from 1987 to 2004.
Five players to fill out your Immaculate Grid: Bill Madlock, Luis Gonzalez, Keith Moreland, Richie Hebner, Kyle Farnsworth
Combined years without a championship: 50
Why this would be fun: The cold weather joke aside (anybody who was at Games 3 and 4 in Detroit in the 2012 World Series can attest to the possibility of needing to wear their winter parka in late October in Detroit), this looks as if it might be the ultimate battle of the bullpens. So, no, not exactly 1907 when Cubs starters Jack Pfiester, Ed Reulbach, Orval Overall and Mordecai “Three Finger” Brown reeled off four consecutive complete games to defeat the Tigers. This might be the ultimate second-guessing matchup as Cubs manager Craig Counsell would have to know how to deal with Detroit’s two lefty sluggers, Kerry Carpenter and Riley Greene, while Hinch would churn through his relievers in the non-Skubal starts.
Best potential drama: If he gets healthy, Cubs rookie Cade Horton could get his postseason moment. Horton was one of the best starters in the majors in the second half, going 8-1 with a 1.03 ERA in 12 games while allowing a .154 average and just three home runs in 61⅓ innings. He allowed more than one run just once. Horton, however, missed the wild-card series with a right rib fracture and is still out for the NLDS against the Brewers.
Aside from that, we would get Javier Baez, who was part of Chicago’s 2016 title-winning (and drought-breaking) team, going against the team he spent his first eight seasons with, as well as Cubs starter Matthew Boyd facing a Detroit team he was with for seven seasons.
If you like Joe Carter highlights: Blue Jays vs. Phillies
This would be a rematch of the underrated 1993 Fall Classic, which featured the wildest game in World Series history — a 15-14 slugfest in Game 4 that the Blue Jays won — and, of course, Joe Carter’s walk-off, three-run homer against Mitch Williams in Game 6.
Five players to fill out your Immaculate Grid: Roy Halladay, Scott Rolen, Jose Bautista, Jayson Werth, Juan Samuel
Combined years without a championship: 49
Why this would be fun: Well, all the highlight clips from the 1993 World Series would be worth it by themselves — not just Carter hitting the biggest home run of his life but the star-studded rosters of both teams that included Rickey Henderson, Roberto Alomar, Paul Molitor, John Olerud, Curt Schilling, John Kruk, Lenny Dykstra and Dykstra’s chewing tobacco.
Aside from that, we would have the Blue Jays in the World Series for the first time since those back-to-back championships in 1992-93 and the Phillies trying to finally win with this roster that is aging and has Schwarber heading into free agency in the offseason. We also would get one of the best uniform matchups in the sport. The Phillies, in my opinion, have the best uniform set in the majors, while the Jays have the classic baby blues to go with their traditional home whites. Do not underestimate the value of a good uni matchup.
Oh, and both fan bases are among the loudest in the sport — Phillies crowds are notoriously loud from the first pitch of games, although Blue Jays fans probably broke the noise meter back in 2015 when Jose Bautista hit that grand slam against the Rangers.
Best drama: Jeff Hoffman facing his former teammates. Last year with the Phillies, Hoffman was an All-Star who had a dominant regular season before losing two games in the NLDS against the Mets. In 2025, he had an uneven season as the Blue Jays’ closer, allowing 15 home runs — the second most of any reliever — but saving 33 games. Hoffman facing Schwarber and Harper with the game on the line would be the reverse tension of Williams facing Carter in 1993.
If you like center fielders: Mariners vs. Cubs
The Cubs owe a little favor to the Mariners for ending their World Series curse in 2016. Mike Montgomery, whom Chicago acquired from Seattle at the trade deadline in 2016 for Daniel Vogelbach and Paul Blackburn, recorded the final out of the Game 7 victory — certainly one of the most obscure pitchers to get the last out of a World Series.
Lou Piniella managed the Mariners from 1993 to 2002 and the Cubs from 2007 to 2010, making the playoffs four times with Seattle and twice with Chicago, but he couldn’t guide either team to a World Series. The two teams shared another manager in Jim Lefebvre.
Five players to fill out your Immaculate Grid: Jamie Moyer, Goose Gossage, Steve Henderson, Gary Matthews, Heathcliff Slocumb
Combined years without a championship: 57
Why this would be fun: Julio Rodriguez and Pete Crow-Armstrong. They were the two best center fielders this season — and two of the most exciting players in the sport — with Rodriguez ranking fifth among all position players in Baseball Reference WAR and Crow-Armstrong ranking 11th. They also ranked 13th and 15th in FanGraphs WAR. Both finished with 30-30 seasons.
Both provide power, speed and highlight-reel catches in center field. J-Rod got hot in the second half: He hit .290/.341/.560 after the All-Star break with 18 home runs and 45 RBIs in 65 games. Crow-Armstrong looked like the NL MVP in the first half when he had an .847 OPS with 25 home runs and 27 stolen bases before hitting just .216 after the break.
Best potential drama: The Mariners winning the World Series? That’s all the drama some of us need.
If you like villains: Yankees vs. Dodgers
Lots of history between these two teams, with 12 World Series matchups, including last year when the Dodgers won in five games.
Five players to fill out your Immaculate Grid: Rickey Henderson, Willie Randolph, Robin Ventura, Kevin Brown, Darryl Strawberry
Combined years without a championship: 16 (long years for the Yankees)
Why this would be fun: Haters are going to hate, and it would certainly be understandable if you’re not a Yankees or Dodgers fan considering the purchasing power of these two franchises. Indeed, though the Yankees held the “villain” title among the general population of baseball fans for the longest time, the Dodgers have usurped them in recent years with their slew of high-priced free agents (Ohtani, Yoshinobu Yamamoto, Blake Snell, Freddie Freeman, Tanner Scott) and big extensions (Mookie Betts, Tyler Glasnow). Heck, even Yankees owner Hal Steinbrenner complained in the spring that it is “difficult” for other teams to keep up with the Dodgers — though he didn’t receive much sympathy.
Still, a rematch would be … dare we say … let’s put this as gently as possible … entertaining! Sure, some of you wouldn’t be able to handle it, but it would be the first World Series rematch since 1977-78, between the … yes, Yankees and Dodgers (the Yankees won both times). The Dodgers would be trying to become that first repeat champion since the Yankees in 2000 to further cement their historical legacy. The Yankees would be trying to end that — for them — long World Series drought since 2009. There would be big stars all over the field. And considering both teams have had bullpen issues, perhaps some late-game drama that could turn this showdown into a seven-game epic.
Best potential drama: Judge vs. Ohtani. This didn’t quite materialize in last year’s World Series when the two MVPs didn’t do much at the plate — Judge hit .222 with one home run (in the fifth game) and three RBIs while Ohtani hit just .105 with no home runs and no RBIs. Of course, now that Ohtani is pitching, it sets the stage for the sport’s two biggest stars going directly head-to-head. That, my baseball friends, is October drama at its best.
