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MLB postseason: Ranking all 25 possible 2021 World Series matchups, from Yankees-Dodgers to Cardinals-Rays

Written by on October 5, 2021

The 2021 regular season is complete and the postseason is set to begin Tuesday night with the AL Wild Card Game. The NL Wild Card Game follows Wednesday, then the ALDS and NLDS begin Thursday and Friday, respectively. The long marathon is over and the sprint to the finish is about to begin.

Here is the 2021 MLB postseason bracket:

The Dodgers are looking to become baseball’s first repeat World Series winner since the Yankees won three consecutive championships from 1998-2000. We are in an unprecedented era of parity in baseball.

Five postseason teams per league means there are 25 possible World Series matchups and we’re here to rank all of them. What are we ranking the matchups on, exactly? Team quality, historic rivalries, geographic rivalries, stuff like that. The rankings are highly subjective, but feel free to tell us we’re wrong anyway.

After consulting with the other CBS Sports MLB scribes, I present to you our 100 percent accurate possible World Series matchup rankings for 2021. Come with me, won’t you?

Good, but not great

Let me start by saying there is no such thing as a bad World Series matchup. All 10 postseason teams are great and fun to watch. It’s just that some are more fun to watch than others. The bottom of our rankings: 

25. Cardinals vs. Rays
24. Braves vs. Rays
23. Braves vs. White Sox
22. Astros vs. Cardinals
21. Braves vs. Red Sox
20. Astros vs. Braves

There is some history here — the Braves and Red Sox once shared a city, and you may have heard about the Astros-Cardinals hacking scandal — but honestly not much. Last year’s ALCS watered down the “Charlie Morton vs. the Astros” storyline. I suspect I am underrating a possible Braves vs. Rays series, though these matchups are generally short on big-name star power, especially with Ronald Acuña Jr. and Justin Verlander injured. Good teams and good matchups, all of ’em, but I reckon most would feel underwhelmed with these World Series.  

Could be worse

This tier has a little of everything. Big markets vs. small markets, powerhouse contenders vs. up-and-comers, and young stars vs. big name veterans.  

19. Brewers vs. Red Sox
18. Braves vs. Yankees
17. Brewers vs. Yankees
16. Giants vs. White Sox
15. Astros vs. Giants

Brewers vs. Yankees is the ultimate small market vs. big market World Series matchup this year. Pretty much everyone outside New York would be pulling for Milwaukee in that one. The Yankees and Braves have some recent-ish World Series history (1996 and 1999), the Giants and White Sox some not-so-recent World Series history (1917), otherwise this tier is a little short on big head-to-head storylines. MLB and the television networks love those. Maybe Jackie Bradley Jr. returning to Boston does the trick?

These will do

Now we’re starting to get into the World Series matchups that would excite all baseball fans, not just the diehards or the locals. Let’s begin the march toward the top of our rankings.

14. Cardinals vs. Red Sox
13. Cardinals vs. Yankees

The Cardinals and Red Sox have met in the World Series four times (1946, 1967, 2004, 2013) while the Cardinals and Yankees have met in the World Series five times (1926, 1928, 1942, 1943, 1964). There’s a lot of history here, though most of it is ancient. I have to admit, knowing Yadier Molina and Adam Wainwright are returning in 2022 takes a little spark out of a Cardinals vs. Red Sox World Series. The “Molina and Wainwright get revenge for 2013, then ride off into the sunset” storyline would have been juicy. The race isn’t close, though Yankees vs. Cardinals would represent the most World Series title vs. the second-most World Series titles (27 to 11).

12. Astros vs. Brewers

Lots of intrigue here. Brewers president of baseball operations David Stearns cut his teeth as Jeff Luhnow’s assistant general manager in Houston before joining Milwaukee, and then of course there’s Josh Hader. Hader went from the Astros to the Brewers as a prospect in the big Carlos Gómez/Mike Fiers trade in 2015. That deal didn’t work out so great for Houston. Imagine if had Hader roaming in their bullpen the last few years, particularly in 2019? Milwaukee’s powerhouse pitching staff against the highest scoring offense in baseball would be an incredible matchup.

11. Brewers vs. White Sox

The closest we can get to an all-Chicago series. I reckon both fan bases would travel well, giving us “home games on the road” vibes throughout the series. The two pitching staffs are excellent, though Chicago definitely has the edge offensively, at least on paper. These two teams are many things and boring is not one of them. Give me Tim Anderson and Willy Adames, José Abreu and Lorenzo Cain, Christian Yelich and Eloy Jiménez, etc.

10. Giants vs. Red Sox

A lifetime ago the Red Sox beat the (New York) Giants in the 1912 World Series, and these two teams have managed to avoid each other in October ever since. The roster construction is very different here. San Francisco is the epitome of depth, with a few true stars and good players 1-26 on the roster. Boston is a bit more top heavy with several bona fide star-caliber producers, though the bottom of the roster can be a weakness. The Giants and Red Sox have combined to win seven of the last 17 World Series, so fatigue is a possibility here. 

9. Giants vs. Yankees

This is the second-most common matchup in World Series history, with the Yankees winning five times (1923, 1936, 1937, 1951, 1962) and the Giants winning twice (1921, 1922). I appreciate the 2009 Yankees vibes the 2021 Giants give off. The 2009 Yankees had an aging championship core (Derek Jeter, Andy Pettitte, Jorge Posada, Mariano Rivera, etc.) and were trying to get them one more title. The 2021 Giants have an aging championship core (Brandon Belt, Brandon Crawford, Buster Posey, etc.) and are trying to get them one more title. You could do a lot worse than Crawford, Posey, Aaron Judge, Giancarlo Stanton, et al on the same field in the World Series. Free storyline for the television networks: Crawford and Gerrit Cole are brothers in law (Cole is married to Crawford’s sister).

8. Giants vs. Rays

The Rays vs. the West Coast Rays. I’d say the Giants are closer to the West Coast Rays than the Dodgers at this point because the Dodgers have done some serious superstar hunting the last few years (Mookie Betts, Max Scherzer, Trea Turner, etc.), and that’s just not a thing the Rays do or the Giants have done, at least not until trading for Kris Bryant. Don’t ask me why, but LaMonte Wade Jr. feels like someone who should be on the Rays and Drew Rasmussen feels like someone who should be on the Giants. The best team in each league always makes for a good World Series matchup, right?

7. Dodgers vs. White Sox

These two teams have met in the World Series once before (1959), so there’s not much history, but look at the two rosters. With all due respect to the guys the Brewers are going to run out there, this is almost certainly the best potential pitching series. Consider the possibilities:

Clayton Kershaw’s injury takes a bite out of Game 4, and Rodón’s late-season injury makes him something of a question mark, otherwise those are some really great pitching matchups. Sign me up for Mookie Betts and Trea Turner sharing a field with Tim Anderson and Luis Robert, and the two teams combining for four All-Star closers (Liam Hendriks, Craig Kimbrel, Kenley Jansen, Blake Treinen).

6. Cardinals vs. White Sox

The Tony La Russa bowl. La Russa left the Cardinals on good terms (literally on the heels of a World Series title), so there’s no bad blood or animosity, but it sure is a juicy matchup. The Cardinals have a roster of grizzled veterans and a manager who is still relatively new (Mike Shildt). The White Sox are the opposite. The roster is young and a bit inexperienced, especially in the postseason, yet their manager has seen it all. Fun teams, though I can’t put this matchup any higher because you know we’re going to get beat over the head with the La Russa storyline, and it’ll get old fast.

5. Brewers vs. Rays

The ultimate baseball nerd matchup. Two very good, very exciting teams that hooked up for a significant trade earlier this year (Willy Adames for JP Feyereisen and Drew Rasmussen), creating added intrigue. There’s also been a ton of front-office overlap here (lots of executives have worked for both Milwaukee and Tampa), though most fans don’t care about that. On the field, this would be a riveting series between young clubs loaded with pitching. MLB would almost certainly hate it because let’s be real, the Brewers and Rays aren’t big ratings drivers, but the fans who do watch will be happy they did. 

It must be noted this is the only possible 2021 World Series matchup between two franchises that have never won a World Series. One of these two teams would walk away with their first ever championship.

Revenge series

There is a chance, maybe even a good one, we’ll get a World Series matchup this year that is a rematch of a recent World Series. Every pennant winner of the last four years reached the postseason except one (sorry, Nationals), creating plenty of rematch opportunities. And in these cases, the rematches come with added intrigue.

4. Dodgers vs. Rays

The Rays vs. the Rays with money. The Rays with money won last season, and both teams are even better this season. This year Max Scherzer and Trea Turner have joined Mookie Betts and Walker Buehler, while Wander Franco and Nelson Cruz have joined Randy Arozarena and Brandon Lowe. It’s too bad Clayton Kershaw is hurt and Blake Snell has been traded though. They would have added another fun storyline. Anytime you get a repeat World Series matchup, fan apathy is a possibility, though I think the Dodgers and Rays will interest enough folks. Who doesn’t love a David vs. Goliath story?

3. Dodgers vs. Red Sox
2. Dodgers vs. Astros

The ultimate revenge series. The Dodgers lost the 2017 World Series to the Astros and the 2018 World Series to the Red Sox, and a few years later the 2017 Astros and 2018 Red Sox were confirmed to be cheaters by MLB. The two clubs were found to have used electronics illegally to steal signs during their championship seasons, and although MLB’s investigation found no evidence they cheated during the postseason, good luck convincing the Dodgers that was the case. Mookie Betts vs. the Red Sox would be a fun story too, though the sign-stealing scandals are going to dominate the headlines. These are our best chances at a World Series where one team legitimately hates the other (particularly Astros vs. Dodgers), and as long as it doesn’t spill over into beanballs or benches-clearing brawls, bad blood is not a bad thing.

MLB’s dream matchup

Give the folks in the commissioner’s office and at the television networks a truth serum, and I’m certain they would tell you this is the matchup they want to see. There can only be one choice for the No. 1 slot.

1. Dodgers vs. Yankees

What, did you expect something else? With all due respect to the Astros and Giants and every other 2021 postseason team, the Yankees and Dodgers are baseball’s two glamour franchises. They’re in the game’s largest markets and the Dodgers have a deep and dedicated fan base in New York thanks to their Brooklyn days. The Yankees? Their fans are everywhere.

Eleven times the Yankees and Dodgers have met in the World Series, far and away the most World Series matchups between any two teams in baseball history. A rivalry recap:

  • 1941 World Series: Yankees win 4-1
  • 1947 World Series: Yankees win 4-3
  • 1949 World Series: Yankees win 4-1
  • 1952 World Series: Yankees win 4-3
  • 1953 World Series: Yankees win 4-1 (at 25, Vin Scully becomes youngest World Series broadcaster ever)
  • 1955 World Series: Dodgers in 4-3 (Jackie Robinson steals home in Game 1)
  • 1956 World Series: Yankees win 4-3 (Don Larsen throws a perfect game in Game 5)
  • 1963 World Series: Dodgers win 4-0
  • 1977 World Series: Yankees win 4-2 (Reggie Jackson hits three homers in Game 6)
  • 1978 World Series: Yankees win 4-2
  • 1981 World Series: Dodgers in 4-2

Imagine Gerrit Cole vs. Max Scherzer in a matchup of aces in their prime (hard to argue Scherzer isn’t still in his prime, no?). Aaron Judge and Mookie Betts doing amazing things despite very different statures. Giancarlo Stanton’s exit velocity vs. Trea Turner’s sprint speed. On and on it goes. Another Yankees vs. Dodgers matchup in the World Series would have it all. Great teams, great players, historic significance, rabid fan bases, and bright lights.

I know many — many — baseball fans out there are sick of hearing about the big-market goliaths each year. Believe me, I know, but we had a preview of this series back in August 2019 (the Yankees won two of three in Los Angeles), and the atmosphere was electric. The Yankees and Dodgers are the best World Series matchup baseball has to offer this year.

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