World Series Predictions: Who's Going to Win It All?

Fittingly, a season like no other will end with a postseason like none before it.

Ready for October? A weird season has produced an even weirder postseason, with 16 teams vying for the title, including two (!) clubs that finished with a losing record. The road to the fall classic begins this week with all eight wild-card series beginning on Tuesday (AL) or Wednesday (NL) and wrapping up by Friday. The postseason has never been more of a crapshoot, meaning World Series predictions have never been more difficult to pin down.

Will the best squads from July to September keep rolling? Will the wild-card round result in jarring upsets? SI's MLB experts predict the World Series matchup and winner, make a bold prediction and select a dark horse candidate to win it all. Here we go.

Tom Verducci

World Series Prediction: Dodgers over Rays (seven games)

Nothing happened this season to get me off my preseason World Series pick. The deepest pitching staffs in baseball proved their worth. No team has won more games using five or more pitchers than the Dodgers and Rays. The postseason format only enhances that strength; no off days in the first three rounds means depth of pitching is more important than in a typical postseason.

Dark Horse World Series Contender: Indians

Their pitching staff leads the majors in strikeout to walk ratio. They are an above-average defensive team. They are playing well down the stretch. (That’s a nice confidence boost, but history tells us there is no big advantage to being hot or not down the stretch, though it makes for a nice narrative.) They just don’t score a lot of runs, so their margin of error is small.

Bold Prediction

Like John Elway, Phil Mickelson, David Price and other athletes whose big game “legacies” were written prematurely, Clayton Kershaw, with his increased velocity and use of analytics (he throws the highest rate of breaking pitches in baseball, 59%), will have his signature postseason.

Stephanie Apstein

World Series Prediction: Dodgers over Rays (five games)

Sorry to pick chalk here, but the Dodgers are so good and the Rays have the pitching depth that will be useful in this no-days-off world. In the end, though, it's hard to see anyone toppling L.A.

Dark Horse World Series Contender: Padres

If they survive the Dodgers, I think the Padres become the favorite. But surviving the Dodgers is going to be very, very hard. 

Bold Prediction

Clayton Kershaw, World Series MVP. In 2008, this might not have seemed so bold. After more than a decade of postseason collapses, I think it qualifies. But his legacy may benefit from the lack of off-days in the early rounds: Most of his October struggles have come when the Dodgers overextended him—using him in relief, asking him to start on short rest—and now they probably can't do that. If he starts every fifth day, and does nothing else, I think he's got one or two stunning playoff performances in him this year.

Emma Baccellieri

World Series Prediction: Dodgers over Twins (six games)

This Dodgers club was bound to win sometime. They’ve been predictably solid this season. Their depth has them well-suited to the no-days-off nature of this October. And what’s typically their biggest playoff problem area, the bullpen, is stronger than ever, even with the unfortunate recent loss of Caleb Ferguson.

Dark Horse World Series Contender: White Sox

There’s no team that’s been more fun to watch in the American League, and they have the chance to make a deep run in the playoffs, too. With two serious MVP candidates in José Abreu and Tim Anderson, plus a strong rotation led by Lucas Giolito and Dallas Keuchel, they shouldn’t be a surprise to keep playing to the end of October.

Bold Prediction

The Marlins in the World Series is a little too bold for my taste. But the Marlins in the NLCS? Bring it. This would be both the perfectly absurd outcome that this season demands on an aesthetic level and also, given the organization of the bracket, an entirely possible baseball result.

Connor Grossman

World Series Prediction: Padres over Yankees (six games)

1998 revenge series, anyone? Seems fitting that this weird season will produce a first-time champion. The Padres have elite pitching and a lively offense fueled primarily by Fernando Tatis Jr. and Manny Machado. The Yankees are the Yankees, full of stars and villains and expensive players. Does anyone not want to see this World Series? No. Of course not.

Dark Horse World Series Contender: Athletics

The A's are a No. 2 seed, so they didn't exactly sneak their way into October. But they were almost unanimously SI's pick for the top team mostly likely to lose in the wild-card round. Oakland finished the season with best bullpen ERA in baseball. Pitching depth has never been more important in October. The offense is just OK, but still, don't be surprised to see the A's go on their first deep playoff run in years.

Bold Prediction

Luke Voit will set a new MLB record with 10 home runs this postseason. The current record is eight but teams will play more postseason games than ever this year, so it won't be a complete shock to see a new record set. The Yankees' surprising MVP candidate will be the man to set the new mark.

Matt Martell

World Series Prediction: Yankees over Dodgers (seven games)

The difference between the Yankees now and the Yankees of the last three seasons that got bounced from the playoffs is their starting pitching. This year, because of the lack of off-days in the postseason, strong starting pitching is going to be crucial. They have the ace, Gerrit Cole, and they have Masahiro Tanaka, who's one of the better postseason pitchers over the last few decades. Not to be overlooked are veteran starter J.A. Happ and 21-year-old rookie Deivi García, likely the fourth playoff starter. Mix in the Yankees' now-healthy lineup and deep bullpen, and there's no doubt New York is the AL team most likely to beat the Dodgers. They'll pull it out this year in seven games.

Dark Horse World Series Contender: Cubs

The Cubs are angry entering October. Five years ago they were the ideal model for what a winning team should look like, and now they're overshadowed by the up-and-coming White Sox. But let's not forget how good these Cubs can be. Many of the core players from their World Series days are still around, and Yu Darvish and Kyle Hendricks are as good as any playoff team's top-two starters. If Kris Bryant, Anthony Rizzo and Javy Báez can come alive in the postseason, the Cubs could be tough to beat.

Bold Prediction

If the Dodgers don't win the NL pennant it will be because they lost to the Marlins en route to winning the World Series. There really is no way to justify this other than Miami has an unblemished postseason resumé and it's 2020. Imagine the chaos of the Marlins winning their third World Series title in their third postseason appearance, and getting there by knocking off the Dodgers. Naturally, if that happened, it would end up coming against the Blue Jays. Imagine those ratings, Rob Manfred. Imagine.

Michael Shapiro

World Series Prediction: Dodgers over Rays (six games)

The Dodgers feel like a relatively safe bet in the National League given the other contenders' relative shortcomings. In the American League, Tampa's collection of arms is unmatched in the American League, and Tyler Glasnow could be the breakout star of the playoffs. Will it be enough to take down the Dodgers? Perhaps. But Mookie Betts is the tide that lifts all boats in Los Angeles. He should be enough to push the Dodgers over the top. Perhaps the result could be different if the Rays had World Series games at The Trop. In 2020, the World Series is the Dodgers' to lose.

Dark Horse World Series Contender: Astros

This is a more than simple respect for the reigning American League champs. We can't overlook that the Astros finished with a losing record. But there is still another gear for this lineup, one that remains stacked with talent even if Jose Altuve continues to struggle. And Houston once again appears to be finding success from unlikely sources in its pitching staff. Cristian Javier and Framber Valdez have been revelations. Zack Grienke continues to cruise in Year 17. Perhaps it's not the most heartwarming story, but bet against the Astros at your peril.

Bold Prediction

The Marlins beat the Cubs in the wild-card round. A three-game series without fans marks the perfect conditions for an upset, especially when the lower seed has superb starting pitching. That's exactly what we have with Miami. Sixto Sanchez is drawing comparisons to Pedro Martinez, and Sandy Alcantara has a 2.25 ERA in his last four starts after missing significant time due to COVID-19. The Marlins appear to be building something after a rocky start to their rebuild. They could arrive as relative contenders sooner than later. 

Max Goodman

World Series Prediction: Dodgers over Rays (six games)

While I think it will come down to a battle between the Yankees and Rays for the American League pennant, this will finally be the year for Los Angeles to be the last team standing. After the first round, the top-seeded Dodgers can stay in Arlington all the way through the final game of the World Series. Only question is, will they run into this year's version of the 2019 Nationals?

Dark Horse World Series Contender: Reds

The Cincinnati Reds can make some serious noise in October. When it comes to starting pitching, Cincy can twirl it with the best of 'em. Any lineup could struggle mightily against a rotation that includes Trevor Bauer, Luis Castillo and Sonny Gray. If offseason additions Nick Castellanos and Mike Moustakas can find their stroke at the right time, even the Dodgers would be susceptible for an upset.

Bold Prediction: 

The Marlins will advance at least to the second round of the postseason. With pitching poised to be a deciding factor, I can see Miami's pitching—headlined by Sixto Sánchez—shutting down a top seed. Remember, Miami has never lost a single series in the postseason in franchise history...

Max oversees SI's Yankees coverage for Inside the Pinstripes.

Chris Halicke

World Series Prediction: Dodgers over Twins (six games)

The Dodgers may be the easy pick, but for good reason. They are the most complete team in baseball and have consistently been great all season. The Twins are my pick out of the American League with their strong pitching and solid lineup. I just have a hard time believing any team in the American League can stop the Dodgers.

Dark Horse World Series Contender: Padres

I’ve liked this team dating back to Spring Training 2.0. They’re young and very talented. I love the way they play the game. They’ve shown this season when they get hot, they are nearly unbeatable. If they can get into a groove by the NLDS, they may be the only team who can knock off the Dodgers. In Fernando Tatís Jr., they also have arguably the most exciting star we’ve seen in baseball since Mike Trout, which makes them easy to root for. 

Bold Prediction

The A's will lose in the wild-card round. Under normal circumstances, I would have them going further into the postseason. They have a very strong pitching staff and a bullpen that can protect leads. However, they have had a hard time consistently producing at the plate all season and they are without one of their best hitters in Matt Chapman. They also played four doubleheaders in September, which is not ideal for any team down the stretch. 

Chris oversees SI's Texas Rangers coverage for Inside the Rangers.

Matt Loede

World Series Prediction: Rays over Cubs (six games)

The Rays pitching with Tyler Glasnow, Blake Snell, Josh Fleming and Charlie Morton is right at the top, if not the best in all of baseball. In the playoffs, it's all about pitching. The Cubs have been consistent all season, and while most will put the Dodgers in the Fall Classic for the NL, I don't trust L.A. in October. 

Dark Horse World Series Contender: Astros

Been there, done that. The Astros know what it takes to be successful in October, and while their offseason and season itself has been chaotic, the team is still built to be a contender, and if they can get past the Twins in the best-of-three, they will gain a ton of confidence that could lead them deep into October.

Bold Prediction:

There's just something about the Dodgers that has me worried that they could be headed for a massive letdown once the postseason begins. I think they'll lose in the wild-card round. Going back to 2013 this team has played a lot of postseason series, 13 to be exact, and have not been able to clinch a title. They've spent tons of money, made trades, and done all they could to be a champion, but I think a scrappy Brewers team could unseat the NL's top squad.

Matt oversees SI's Cleveland Indians coverage for Cleveland Baseball Insider.