MLB playoffs: Ranking 10 best possible 2020 World Series matchups with postseason field set


The 60-game regular season is in the books and the 2020 MLB postseason begins Tuesday with the first ever Wild Card Series. MLB and the MLBPA agreed to an expanded 16-team postseason field this year and the best-of-three Wild Card Series will be a prelude to the LDS, LCS, and World Series.

Here are the first-round matchups:

Eight teams per league equals 64 — 64! — possible World Series matchups. The sheer numbers mean this postseason offers greater variety and the best-of-three Wild Card Series makes upsets more likely. Bad teams take two of three from good teams all the time. We see it every week. A bad 72 hours (or even a bad 48 hours) and your season could be over.

With the largest postseason in MLB history upon us, let’s rank the 10 World Series matchups we’d most like to see this year. Our highly subjective rankings are based on team quality, entertainment potential, head-to-head play, historical significance, etc. Here are the best possible World Series matchups.

The Cubs winning the World Series four years ago removes some drama from this potential matchup, otherwise it might’ve ranked No. 1 seeing how it would’ve been the longest championship drought vs. the team with the most championships. As things stand in 2020, we have two historic franchises with some very big-name stars (Javier Baez, Gerrit Cole, Aaron Judge, Anthony Rizzo, etc.) and two diehard fan bases. It’s a shame the series would be played at Globe Life Field in Arlington rather than Wrigley Field and Yankee Stadium. These two clubs have met in the World Series only twice: 1932 and 1938. The Yankees swept both series and Babe Ruth kinda sorta maybe possibly called his shot in Game 3 in 1932.

9. Cleveland vs. Reds

An intrastate World Series matchup and this year’s all-pitching World Series matchup, at least when it comes to starting pitching. The Reds will be extremely formidable in a short series thanks to Luis Castillo, Sonny Gray, and former Cleveland hurler Trevor Bauer. Cleveland can counter with Shane Bieber, who should win the Cy Young unanimously, then some combination of Carlos Carrasco, Aaron Civale, Triston McKenzie, and Zach Plesac. How fun. Also, this would be a first! Even though these two franchises have been around basically since the dawn of time, they’ve never once met in the World Series. That’s a neat little sidebar.

If Cleveland and the Reds are the all-pitching matchup, the White Sox and Braves are the all-offense matchup. Atlanta was the highest-scoring team in baseball during the regular season while Chicago was merely top 10, but gosh, look at the position by position breakdown:

Right field is lacking, sure, but this matchup offers at least one brand name at every other position and often two brand names. How fun. Atlanta’s rotation is thin and the middle of Chicago’s pitching staff is a bit weaker than a World Series contender would like, and that’ll only help the offense even more. This could be one of the highest-scoring World Series matchups ever (now watch every game finish 2-1 or 3-2).

Not gonna lie, I am sorta sick of the Astros vs. Dodgers buzz. We’ve already experienced it twice this year — the Dodgers won three of four against the Astros during the regular season — and the season series featured Joe Kelly throwing at (and mocking) various Astros, and Houston mounting an enormous comeback against Kenley Jansen. I’m over the narrative though. Call it sign-stealing scandal fatigue. That said, I can’t deny these two teams tend to play very exciting baseball. A 2017 World Series matchup has to be in the top 10.

6. Rays vs. Dodgers

The ultimate David vs. Goliath matchup with an added dose of Andrew Friedman intrigue. The Dodgers, Friedman’s current team, are the model organization thanks to their blend of small-market savvy and big-market payroll. The Rays, Friedman’s former team, continue to succeed despite shoestring budgets because they out-smart and out-innovate everyone else. The Rays wouldn’t be at full strength because they’ve had so many pitching injuries, but they’re still plenty good enough to give the Dodgers headaches. An easy underdog to root for, they’d be.

5. White Sox vs. Cubs

This is the only possible same city World Series matchup this year, and it is damn shame it would be played at Globe Life Field in Arlington (possibly without fans) than in Chicago. Wrigley Field is an iconic venue and the fan bases would undoubtedly invade the other’s ballpark. It would’ve been so much fun. Alas.

Even at a neutral site, a White Sox vs. Cubs matchup offers plenty of intrigue. There’s a “little brother trying to best big brother” element to it, and White Sox manager Rick Renteria was fired by the Cubs so they could hire Joe Maddon years ago. Think Renteria would love to beat them in the World Series? Also, this would be a rematch of the 1906 World Series, which was arguably the biggest upset in baseball history as the 93-58 ChiSox knocked off the powerhouse 116-36 Cubs in six games.

4. Yankees vs. Dodgers

The dream World Series matchup. For MLB, that is. A not insignificant number of baseball fans have Yankees and Dodgers fatigue — believe me, I get it — which is why I’m not ranking this matchup higher than No. 4, but it’s a marketing department’s dream. An ultra-popular large market team on each coast with stars aplenty. Mookie Betts vs. Gerrit Cole, Aaron Judge vs. Clayton Kershaw, so on and so forth.

There’s also the history. The Dodgers of course originated in Brooklyn and still have a very loyal following in New York as fandom gets passed down from generation to generation. Also, Yankees vs. Dodgers is the most common World Series matchup in history. These two teams have met 11 times in the Fall Classic with the Yankees holding an 8-3 series edge. Los Angeles won the most recent World Series meeting in 1981, however.

Both teams are mired in a World Series drought — the Dodgers have not won a championship since 1988 and the Yankees not since 2009, which qualifies as a long drought for that franchise — which adds another layer of intrigue. MLB undoubtedly has Yankees vs. Dodgers atop its desired World Series matchup rankings. For me, it’s No. 4, only because we are overexposed to the two teams.

3. Cleveland vs. Padres

Recent injuries to Dinelson Lamet and Mike Clevinger have changed San Diego’s postseason rotation outlook, but, when healthy, this might’ve been the most fun World Series pitching matchup possible. Clevinger against his former team? It gets no better than that. Now imagine former Padre Franmil Reyes taking him deep.

Beyond the 2020 teams, this matchup features the two longest postseason droughts in each league. Cleveland has not won the World Series since 1948 and the team’s 71-year title drought is the longest in baseball. The Padres have never won the World Series. They joined the National League as an expansion team in 1969, so their championship drought is up to 51 years.

One way or the other, a historically long World Series title drought would end with this World Series matchup. It’s not quite as riveting as 2016, when Cleveland faced the Cubs and their 108-year title drought, but it is the best the sport has to offer right now.

2. Athletics vs. Dodgers

Fun fact: Los Angeles and Oakland are one-two in postseason appearances since 2012. This is the eighth time the Dodgers have been to the postseason since 2012 and the sixth time for the Athletics. No other team has played postseason baseball as often. 

As for this specific matchup, there is of course significant history here. These two teams met in 1988 World Series, which featured maybe the most well-known home run in baseball history. It’s certainly one of the sport’s most iconic highlights.

Thanks in part to Kirk Gibson’s improbable home run, the Dodgers won the World Series in 1988, and they have not won a World Series since. The Athletics bounced back with a World Series title in 1989.

The 2020 edition of a possible A’s vs. Dodgers World Series matchup definitely would have a David vs. Goliath feel, which always creates a fun narrative. You’ve got the plucky small-market team vs. the large-market behemoth. Matt Chapman’s injury removes some star power from this matchup, but it’s still loaded with fun players. The history, the geography, and the quality of the 2020 clubs makes Athletics vs. Dodgers one of the best possible World Series matchups.

1. White Sox vs. Padres

For my money, these are the two most exciting teams in baseball right now. Fernando Tatis Jr. and Tim Anderson are must-watch television, then there’s Trent Grisham and Luis Robert, Manny Machado and Yoan Moncada, Eric Hosmer and Jose Abreu, so on and so forth. The pitching matchups could be great too (as long as the Padres get healthy).

Also, the White Sox and Padres haven’t been good in a while — this is Chicago’s first postseason berth since 2008 and San Diego’s first since 2006 — and they made bold moves to put themselves in this position. The White Sox signed Yasmani Grandal and Dallas Keuchel over the winter, and the Padres added Mike Clevinger, Austin Nola, Trevor Rosenthal, and others at the deadline. Trying is an uncommon trait these days, unfortunately, and teams that try should be rewarded.

The entertainment potential is off the charts with a White Sox vs. Padres series. Long homers, bat flips and creative celebrations, aggressive and high-risk baserunning, and just lots of fun. These two teams are very fun and I’m pro-fun, so this World Series matchup tops my list. There would be no better way to market all the young, exciting talent in the game than with White Sox vs. Padres.

Other matchups we’d love to see

In no particular order …

Athletics vs. Padres: A very fun matchup, no doubt, even without Matt Chapman and possibly Dinelson Lamet and Mike Clevinger. A’s vs. Padres doesn’t exactly scream “rivalry” though, despite sharing a home state.

Blue Jays vs. Padres: The poor man’s version of White Sox vs. Padres. Toronto has some very good, very young position players who haven’t entirely broken out yet, but they play hard and they make the game fun.

Cleveland vs. Cubs: This would certainly rank top 10 — maybe even No. 1 — if they hadn’t met in the World Series four years ago. They had the two longest championship droughts at the time and that intrigue is gone. Still a fun matchup though.

Rays vs. Marlins: Fun fact: the Marlins have never lost a postseason series. They won the World Series in 1997 and 2003, and have never been to the postseason otherwise. Not until this year, anyway. The intrastate matchup would be neat.

Twins vs. Dodgers: Two very good teams that play an exciting brand of baseball. There’s also some history here. In the 1965 World Series, Sandy Koufax struck out 10 in a three-hit shutout in Game 7 on two days rest to beat Minnesota. 

White Sox vs. Reds: Chicago’s offense vs. Cincinnati’s rotation? Lordy. That would be as fun as it gets. Bonus points for being a rematch of the 1919 Black Sox World Series.

Yankees vs. Padres: A David vs. Goliath matchup and a rematch of the 1998 World Series. Not sure two teams could be any more different than these two.





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