Hot Corner Harbor: The Annual 2026 MLB Playoff Trivia Round-Up and Preview!


I’m a little busy this year (not entirely due to my Summer Playlist article that just went up over at Out of Left Field, but it was another thing to do, so it would be cool to go check that out as well if you have time!), but I would really like to keep up with my yearly tradition of Playoff Trivia. So I’m going to try and make it happen through a mix of pre-writing as much as I can and being a little more efficient than I’m used to.
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So with that in mind, let’s jump right in…
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​DROUGHTS​
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It feels like kind of a boring year on the drought front, in spite of the fact that all three of our longest active World Series droughts are represented in the playoffs this year, in the Guardians, Brewers, and Padres. A big reason for that is probably because eight of the past ten World Series winners are represented in this season’s postseason field (and with the also recently-crowned Rangers just narrowly missing out as well).
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That brings the overall numbers down a bunch, despite those three big ones trying to push in the other direction. But it’s really just those three and the Rays (who, like the Padres and Brewers, are searching for their first ever championship, albeit with a much shorter history). Everyone else here has won at least one title since the turn of the millennium. In fact, our median drought for this set falls right in between the Phillies (2008) and Yankees (2009). It’s actually kind of difficult to wind up with a group of teams with a sub-20 year median drought, given that this is a 30-team league and there have been plenty of repeats in that span. This just isn’t a group that skews towards the long-suffering, in general.
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