There’s Only One October 2020: MLB Playoff Predictions

Do you remember, lo those many years ago, when Dane Cook was a Thing? He was everywhere. He even did a series of commercials for the Major League Baseball postseason. Look at this:

The existence of that ad campaign indicates that someone actually wrote a script featuring the phrase, “There’s Only One October.” What? Was the idea to make that a recurring theme, something we would all associate with Fox and MLB for years to come?

Then again, here I am, still talking about it 13 years later, so touché, Dane.

Anyway, even though there’s an October every year, let’s hope there’s only one October like the one we’re about to have, with over half the teams in baseball able to claim they reached the postseason. Conspicuous by their absence, of course, are the hometown Phillies, but that’s a story for another article or podcast or five.

One of the things I like to do is make predictions. I like to make bold ones – I once predicted that Carson Wentz would never start a playoff game for the Philadelphia Eagles, and he’s almost made me look like an oracle on that front – and I also like to make boring ones. What I really like, though, is being right.

Which is why making playoff predictions this year is a terrible idea, but I’m gonna do it anyway. Here is how I see the MLB playoffs shaking out over the next four weeks.

WILD CARD (Best-of-three; all games at higher seed)


#1 Tampa Bay Rays vs. #8 Toronto Blue Jays: We all saw this past weekend how good the Rays could be when they didn’t really have anything on the line. Or maybe they’re just spiteful, I dunno. Regardless, a week earlier, the Phillies took three of four from the Blue Jays, but couldn’t even get a single, season-saving win in St. Petersburg. Using the 2020 Phillies as a barometer of anything is a terrible idea, but I think it gives me the right result here. Rays in 2.

#2 Oakland A’s vs. #7 Chicago White Sox: The White Sox have guys like Lucas Giolito and Dallas Keuchel on the mound, and exciting hitters like Luis Robert, Tim Anderson, and Nick Madrigal in the lineup, to name a few. The A’s have Matt Chapman, Jesus Luzardo, and…see, with this year’s weird scheduling setup, the Phillies didn’t head west – or even west of, like, Atlanta – and with all the sports going on, checking out late night West Coast baseball just isn’t a thing I did much of. I don’t even know if either of those guys are healthy and going to play. So the obvious pick would be the White Sox here, but I’ve been bitten by the “that team isn’t that good, I don’t even know who plays for them” bug in the past. Fool me once, shame on you; fool me twice, people can read it on the internet. A’s in 3.

#3 Minnesota Twins vs. #6 Houston Astros: Not so easy to hit when you don’t know what pitch is coming!

(The bells you hear ringing are the ones signifying the one millionth time someone has made that joke about the Astros.)

However, as tired as the joke may already be, the reason people are making it is because the Astros aren’t doing well at all. One of the bold predictions I was talking about earlier was one I made to a friend when the expanded playoff field was announced: I guaranteed that a sub-.500 team would make the playoffs. He scoffed – via text – but here we are; at the same time, I don’t think anyone would have thought the Astros would be one of them! They’re just not very good. Are the Twins? I dunno. Probably. Twins in 3.

#4 Cleveland Indians vs. #5 New York Yankees: Ah, there’s the stuff. A team on the rise taking on a team that may be on the way down and in the final days of its competitive window.

Except the former is the Yankees, and Cleveland is the latter.

We saw the trades of Trevor Bauer and Mike Clevinger, and we know that the likelihood of Francisco Lindor re-signing by Lake Erie isn’t very high, and a trade that sees him head out of town could come this offseason. Meanwhile, the Yankees have some young talent and went out and acquired the top free agent pitcher in baseball last season in Gerrit Cole. They may also be lurking on the periphery of The J.T. Realmuto Sweepstakes, which will be airing on televisions across the Delaware Valley this fall and winter.

This will probably be the best of the four AL Wild Card series. Now that I’ve said that, expect a pair of blowouts. Yankees in 3.


#1 Los Angeles Dodgers vs. #8 Milwaukee Brewers: I could go deep on this one, but I won’t waste anyone’s time. Dodgers in 2.

#2 Atlanta Braves vs. #7 Cincinnati Reds: The Braves have struggled to piece together a rotation this season, as Mike Soroka went down with an Achillies injury early on, and Max Fried has been dealing with an ankle injury as of late. He’s been cleared to start Game 1 on Wednesday, where he will be opposed by NL Cy Young contender Trevor Bauer. I think the winner of Game 1 will take this series, and I think that’ll be Bauer. Reds in 3.

#3 Chicago Cubs vs. #6 Miami Marlins: When a player tests positive for performance-enhancing drugs, he is suspended for 80 games and is ineligible for that year’s postseason, even if his suspension ends before the regular season is over. I think the Marlins as a team should be ineligible for the postseason after the havoc their 20 COVID-19 positives caused for the league. That said, remember what happened the last time the Marlins played in the postseason in Chicago? Or do we not talk about that anymore since they won a World Series? Whatever, screw the Marlins. Cubs in 3.

#4 San Diego Padres vs. #5 St. Louis Cardinals: The young and fun Padres will host the widely-loathed St. Louis Cardinals, who also should be banned from the playoffs under the Miami Marlins Infectious Disease Corollary, in the series that is most primed for fan disappointment. Out of all the possible results above, wouldn’t the Cardinals topping the Padres be the one that bums out neutral fans the most? The ever-present “lol iT’s 2020 sO oF cOuRsE” logic indicates a sweep by St. Louis, but I’ll go out on a limb and predict that the second-best team in the National League will come out on top. Bold, I know. Padres in 3.

DIVISION SERIES (Best-of-five; all games played at neutral sites)


#1 Tampa Bay Rays vs. #5 New York Yankees (San Diego, Calif.): The Rays won eight of 10 between the two teams this season. I know it’s a small sample size, but that’s not an accident. Rays in 4.

#2 Oakland A’s vs. #3 Minnesota Twins (Los Angeles, Calif.): I kinda teased this answer above, so it should be no surprise to you that I don’t really know what to think about this series. I saw a stat yesterday that said the A’s were 27-0 when leading after seven innings. Let’s use that stat for this pick. A’s in 5.


#1 Los Angeles Dodgers vs. #4 San Diego Padres (Arlington, Texas): Aw, man! The Padres would be a great pick to reach the World Series, and a great team to watch in said World Series, but they have to play the best team in baseball in what amounts to the quarterfinals. That sucks. Dodgers in 4.

#3 Chicago Cubs vs. #7 Cincinnati Reds (Houston, Texas): My picks have been pretty chalky thus far, which means they’re almost certainly wrong. That said, I think something weird has to happen, and the third place team from the NL Central reaching the NLCS is pretty weird. Not quite 2020-level weird, but weird enough. Reds in 5.

CHAMPIONSHIP SERIES (Best-of-seven; all games played at neutral sites)


#1 Tampa Bay Rays vs. #2 Oakland A’s (San Diego): I’m looking at the venue here. A notorious pitcher’s park, Petco Park will help the Rays and their outstanding pitching keep the A’s in the yard, and will propel Tampa Bay to its second World Series appearance. Rays in 6.


#1 Los Angeles Dodgers vs. #7 Cincinnati Reds (Arlington): This kinda looks like an NCAA Tournament final four, right? Two #1-seeds, a #2-seed, and then a random team seeded fifth or lower. I am hard-pressed for reasons to pick against L.A. Dodgers in 5.

WORLD SERIES (Best-of-seven; all games in Arlington)

Tampa Bay Rays vs. Los Angeles Dodgers: After seven months of “man, 2020 is crazy, innit?” wouldn’t the craziest thing of all be to see the two teams who were the best all year in their respective leagues face off in the World Series?

The Dodgers are to the mid-to-late 2010s what the Yankees were to the mid-to-late 1990s and early 2000s: the preeminent alpha dog, the team you pencil into the postseason on Opening Day, and the one you expect to lift the trophy in the end. The Yankees won four World Series during that period, but the Dodgers have only been to two, and saw someone else celebrate on their infield both times.

Sixty games is not enough for a baseball season. Imagine having NBA teams play 30 games before starting the playoffs, or kicking off the road to the Super Bowl after Week 6. You wouldn’t entertain the thought of considering that year’s champion to be legitimate for a single second.

And yet, if the Dodgers win the 2020 World Series, I think it really would be legitimate. As I said, they’ve been the best franchise in baseball for a while now, and were World Series favorites before the season, when “before the season” meant February and March, not the Fourth of July. Despite the shortened campaign and the expanded playoff field, I think if the best team in baseball the past few seasons shows up and posts the best record and wins the postseason tournament, then you kinda have to just tip your cap and say yeah, it counts.

However, this season does not deserve to be considered legitimate. The Lightning won the Stanley Cup last night. The Miami Heat are in the NBA Finals. The next Super Bowl is going to be played in Tampa. Florida, the site of multiple professional sports bubbles, is dominating both the sports news and news news cycles.

And THAT, my friends, is 2020 in a nutshell. Of course the Rays are going to win the World Series. Rays in 6.

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