The Big 2025 MLB Postseason Trivia Roundup!

I don’t know that I have much specific to say about this year’s entry in my annual Playoff Trivia Series. Especially not after last year’s version, where I had to fit writing the entire thing in after that last-day double header. This is so much nicer of an experience (especially coming right on the heels of the huge Playlist article that I just published over at Out of Left Field).

Anyway, as a refresher, for those of you looking for a team to bandwagon for this postseason, perhaps this column will be of some use! That’s how it started, as a way for me to compile a whole bunch of interesting factoids about each year’s set of playoff teams and maybe give neutral observers some direction on fun storylines like long droughts or deserving players searching for a win, and it’s been a fun routine for me to preview October every year. So after a brief interruption for the Hot Corner Harbor email list sign-up form, let’s get right into it!

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DROUGHTS

You may not have realized it if you haven’t sat and thought about it yet, but this is actually a fairly cursed set of playoff teams. Our dozen teams includes all four of the longest active World Series droughts. There’s of course Cleveland at the top (last win in 1948), they’re well into that upper-echelon of dry spells. You know, that point where almost every span above them got a fancy title “The Curse of”? I’m not sure if Cleveland fans have settled on a cause of their misfortunes yet, but this might be the point where they should start looking for one.

After them, it’s a bunch of expansion teams who have never won a title. Those usually don’t seem to get “Curse of” titles, for whatever reason; I guess because expansion teams are just expected to be bad? Now that the first wave of new teams from 1961 and ‘62 are all taken care of, the Padres and Brewers (established in 1969) share the runner up title, while 1977 additions the Mariners are our fourth-place team.

It’s not often you get the entire top four in October like this. By my count, the only other time it happened was 2015, which was thanks to the Cubs, Guardians, Rangers, and Astros all showing up. That kind of gets to an interesting point, which is that in the first quarter of the 21st century, we’ve actually lost a lot of our Mega-Droughts. Obviously you have the big three of the Cubs, Red Sox, and White Sox. But the Giants, Astros, Nationals, and Rangers were all also at the fifty-year mark as well, and even the Angels took over four decades to make it to the top when they made it back in 2002. That’s a lot of heavy hitters that just aren’t around any more, making it more shocking that we still see years like this one. 




I said last year that it would be hard to top the 2024 Playoff set last year, since it had our top three droughts plus the six-through-eight teams, but this year has actually done that. We lost the Mets and Orioles, but the Mariners, Reds, and Blue Jays (the latter two both 30+ years) helped offset those absences. Arguably, it’s our second-best year in the Wild Card Era for potential Drought-busting opportunities. By average, it’s fifth, which is impressive considering that every season above it had the pre-2016 Cubs (and two of those four also added the Bambino-cursed Red Sox on top of that). But if you go by median, it moves just past 2016, to second place.

Of course, “Best Potential for Drought Busting” doesn’t always translate into actually ended droughts. The one season indisputably ahead of 2025 was the 1998 postseason, which included the Red Sox, Cubs, Rangers, Astros, Padres, and Guardians… only for the title to instead famously go to the mid-dynasty Yankees.



PLAYERS WITHOUT A WORLD SERIES

Once again, upon the conclusion of this year’s World Series, I will be publishing my annual Sporcle quiz on the “Best Active Players Without a World Series”, with this year’s newest champions freshly removed. I even add each year’s version to a playlist including the past editions; it’s kind of fun to see how these lists evolve over time. If you’d like a preview of who the specific players with a chance to drop of the list are, I’ll include the spoilers at the end of this article (after the final email sign-up box).

I will note that this year’s list feels a little fuller than it has the last few times. We don’t even have a team with zero representatives (I imagine some of that is probably tied to the quantity of long-drought teams here). I don’t really have a hard cut-off for these quizzes; at first, it was usually just “the end of Baseball-Reference’s Top 100 Active Players”, but I’ve gone beyond that for a while now. The 2025 version went all the way down to anyone with 18.0 career bWAR, which felt like a lot in-the-moment (nearly 70 names), but after a peak at the last few lists, it’s actually pretty in-line with the cutoff that I’ve used the last few years. I really thought that I had to pull in more new names to fill things out, but maybe we’re just seeing a lot of turnover instead. Also, there are some weird edge cases here that I’ll explain more in the spoiler section.

One: Dodgers, Guardians, Red Sox, Reds
Two: Tigers
Three: Brewers, Cubs, Padres
Five: Phillies
Six: Blue Jays, Mariners, Yankees



THREE-TEAM PLAYERS

If you aren’t a regular reader of this column, you may not be aware of this rather exclusive club. There are plenty of players throughout history who have won three World Series in their career (if not more), but a lot of those names are guys who played on dynasties that won them a lot of titles. Much more rare are the guys who have won titles with three different teams; we only have eighteen of them, with the most recent being reliever Will Smith (who pulled off the incredibly rare feat of winning his back-to-back-to-back from 2021 to 2023). Three different teams is our highwater mark still, and that won’t be changing this year.

However, we actually have a number of options to join the three-time club, which is very unusual! A lot of them feel like technicalities, but that’s often the case here. Aroldis Chapman (2016 Cubs, 2023 Rangers) is the rare case where he would actually be a core contributor, as the closer on the Red Sox. Max Scherzer (2019 Dodgers, 2023 Rangers) could also make an appearance in October; he probably won’t be in the Blue Jays’ rotation, but you always need people to pick up innings, so he might still make the roster.

Our other options are more of the “they’ll get a ring” variety. Ryan Brasier (2018 Red Sox, 2024 Dodgers) has missed the last month of the season with injuries, and it’s not clear that the Cubs will want to add him to their postseason roster anyway. At least that’s an option, though; the Tigers cut Charlie Morton (2017 Astros, 2021 Braves), letting him finish the season with the Braves (in what feels like the likely end of his career). Meanwhile, the Padres DFA’d Jason Heyward (2016 Cubs, 2024 Dodgers) back in June, and he hasn’t played since (and even that second ring is of the “cut mid-season” variety, meaning that would be the case for two of his three).

There are a few other interesting names here for setting up potential three-team guys down the road, too. Kyle Tucker (2022 Astros) and Kyle Schwarber (2016 Cubs) are both going for their second title before hitting the free agent market this winter. You can expand that pool to include Alex Bregman (2017/2022 Astros), Walker Buehler (2020/2024 Dodgers), Cody Bellinger (2020 Dodgers), and Mitch Garver (2023 Rangers) if you want to include players with options that might be declined. And if you want to go even further and include the free agents for next winter, you add guys like William Contreras (2021 Braves), Jack Flaherty (2024 Dodgers), and George Springer (2017 Astros) as well. Those are probably better bets than guys like Juan Soto or Max Fried, who even if they do pick up a second title this year, probably won’t see a chance to pick up a third team after that thanks to the length of their deals.



EXPANSION TEAMS

Long-time readers may already know this, but ever since MLB started adding expansion teams back in 1961 and 1962, there have only been three occasions where two of them have met in the Fall Classic. It took all the way until 2015 to happen the first time (with the Royals and Mets), but we’ve seen it happen two more times since then in 2019 (Nationals and Astros) and 2023 (Rangers and Diamondbacks). I’m still not sure if we’re finally up to 50-50 odds yet (despite Expansion Teams representing almost half of the league), but it certainly seems closer to that than ever before. I’m also not sure I’ve ever seen an adequate explanation for why it was so rare in the first place, making explaining what changed even tougher.

Less than half of this year’s playoff field is expansion teams, just four out of twelve. But we actually have decent odds of an All-Expansion series in spite of that, since three of them (the Blue Jays, Mariners, and Brewers) earned byes and will skip straight to the Division Series round. Only the Padres will have to fight their way through the Wild Card round, meaning that our chances* of yet another All Expansion Team World Series are roughly at 3 in 16, or 18.75%.

*I’ve usually assumed each series is a coin flip for the purpose of setting the odds here; historically, that’s usually been close enough for our estimate. I’m still not sure if there’s been any evidence yet that securing one of the byes meaningfully affects that assumption (but let me know if you’ve seen anything to the contrary).

While we’re on the subject of the history of expansion teams in October, it’s also worth reflecting on how unusual these specific expansion teams are in this setting. As I mentioned back in the Droughts section, the Padres, Brewers, and Mariners have all never won a World Series before, three of our five remaining titleless teams (along with the Rockies and Rays). The Mariners are of course the only team left (until future expansion) to not have a Pennant, and even the Brewers have not won one for their current league (their lone World Series appearance came way back in 1982, when they were still an AL team).

The Blue Jays, meanwhile, are on the exact opposite side of the expansion team spectrum. They’re one of five expansion teams with two titles (alongside the Mets, Marlins, Royals, and Astros), and they’re looking to beat those other four to become the first one with three. That would even put them above two Original Sixteen teams (Cleveland and Philadelphia), to say nothing of the success of winning the World Series in all of your first three appearances (something I believe only the Red Sox have accomplished, as of right now).



UNIQUE MATCH-UPS

You might think, given the unusual number of long-drought teams, that we’re light on potential rematches. That is not the case, however! That’s of course thanks in part to the presence of the Yankees, who have matched up against twelve of our fifteen NL teams (as well as five of these six playoff teams). That includes their long-standing rivalry with the Dodgers, who they met in the World Series last year for a record-extending twelfth time.

The Red Sox and Dodgers also bring our number of rematches up, but you might also be surprised to see how well-represented the Cubs, Reds, Tigers, and Phillies are too. In fact, the Cubs actually have more potential rematch partners here than the Dodgers! And not only that, but their Tigers “rivalry”* is one of two World Series match-ups that have occurred more than three times without involving any current or former New York team (the other one being the Red Sox and Cardinals).

*Can we call it a rivalry if they haven’t met in the postseason since the year World War II ended? Probably not, but it’s funny to refer to it that way.

Really, part of the reason for that is that those original sixteen teams just had so many opportunities to meet in October before the expansion teams were added. The weird exception to that rule is Cleveland, who’s only faced the Dodgers and Cubs before (the latter or which didn’t happen until 2016). They didn’t have a ton of success in the old days, but unlike the Phillies (another long-struggling original sixteen team), their most common cross-league foes (mostly the Giants and Braves) didn’t make it to October this year. And on the flip-side, we have expansion team San Diego, who has only won the pennant twice but sees both of those foes (the Yankees and Tigers) among the 2025 AL field.

Of course, for those looking for new pairings instead, Seattle and Milwaukee again obviously bring a lot of options to the table, and those two facing each other would even mean pitting Seattle against the former Seattle team (the Brewers moved away after one season). And even two-time champions Toronto have five potential new opponents, since the Braves fell short.

For non-expansion team options, the potential All-Ohio series would be a first. The Dodgers and Tigers have also never met in October despite their long histories (the latter was too busy facing the Cubs, I guess?), and the Phillies against either the Tigers or Guardians would also be breaking new ground (that feels more justified, given the Phillies’ pre-1980 drought). If you’re looking for an anti-NY/LA match-up to root for, I think Milwaukee versus Cleveland is the second smallest pairing of potential MLB markets possible (only ahead of Kansas City).

rematches	PHI	MIL	LAD	CHC	SDP	CIN
TOR	X
DET				X	X	X
SEA
NYY	X		X	X	X	X
BOS	X		X	X		X
CLE			X	X

A Full List of Potential Rematches

Recurring Match-ups
Yankees-Dodgers, 12x (1941, 1947, 1949, 1952, 1953, 1955, 1956, 1963, 1977, 1978, 1981, 2024)
Tigers-Cubs, 4x (1907, 1908, 1935, 1945)
Yankees-Reds, 3x (1939, 1961, 1976)
Red Sox-Dodgers, 2x (1916, 2018)
Yankees-Phillies, 2x (1950, 2009)
Yankees-Cubs, 2x (1932, 1938)

One-time match-ups
Guardians-Cubs (2016)
Yankees-Padres (1998)
Blue Jays-Phillies (1993)
Tigers-Padres (1984)
Red Sox-Reds (1975)
Tigers-Reds (1940)
Guardians-Dodgers (1920)
Red Sox-Cubs (1918)
Red Sox-Phillies (1915)



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PLAYERS WITHOUT A WORLD SERIES, SPOILERS VERSION


Blue Jays: Kevin Gausman, Vladimir Guerrero Jr., Bo Bichette, Andres Gimenez, Shane Bieber*, Chris Bassitt
Brewers: Christian Yelich, Jose Quintana, Brandon Woodruff
Cubs: Carlos Santana, Ian Happ, Nico Hoerner
Dodgers: Blake Snell
Guardians: Jose Ramirez
Mariners: Eugenio Suarez, Luis Castillo, Julio Rodriguez, J.P. Crawford, Jorge Polanco, Cal Raleigh
Padres: Manny Machado, Yu Darvish, Fernando Tatis Jr.
Phillies: Bryce Harper, Zack Wheeler, J.T. Realmuto, Aaron Nola, Max Kepler
Red Sox: Trevor Story
Reds: Wade Miley
Tigers: Gleyber Torres, Tarik Skubal; also maybe Alex Cobb*
Yankees: Paul Goldschmidt, Aaron Judge, Giancarlo Stanton, Gerrit Cole*, DJ LeMahieu, Carlos Rondon, Marcus Stroman

*Bieber, Cobb and Cole actually present some difficulties here. My standard rule is “if the player played for the team during the season, they count”. The reasoning was that I wanted to capture anyone who got a World Series ring, and players have been fairly generous there usually. Each of these players is a unique challenge, though.

Bieber was a longtime member of the Guardians, and was on their roster this season up until the trade deadline. However, he did not actually throw an inning for the major league club before being traded to a competitor (just their minor league clubs, as part of his rehab). Would the team still give him a ring if Cleveland wins? Cobb and Cole are a little less convoluted, since they’ve been on their team’s rosters for the full season, they have been injured the whole time. I can’t imagine Cole would be denied a ring if the Yankees win since he’s been an important member of their last few teams, and will be back next year. Cobb is more debatable since he only signed last winter and never threw a pitch for Detroit, although he did have a brief rehab stint in their minor league system before his injuries resurfaced.

So, how do all of these cases change my thinking on my rule at all? Do I stick to the wording I’ve used, or the intent I was originally trying to describe? Maybe this will become a moot point, but I should probably be thinking about it just in case, since there are so many potential pitfalls this time.