There’s just something about postseason baseball that makes me always want more of it. And when it’s over, I go through intense feelings of withdrawal. Everything is magnified: a first-pitch strike, the first team to score a run, a postseason grand slam (especially when a certain kind has only happened four times)… you get the idea.
While everyone wants their favorite team playing in October, it’s also inherently more stressful. But if you’re just enjoying the atmosphere and don’t have a vested interest in the outcome, it’s much easier to appreciate each big moment.
Postseason home runs can act as daggers. That’s especially true of a pinch-hit homer, and even more so of a pinch-hit grand slam. But here’s the thing — pinch-hit postseason grand slams have only happened four times in MLB history! And one occurrence in particular stands apart from the rest.
Every Pinch-Hit Postseason Grand Slam in MLB History
Mark Lewis, Cincinnati Reds
When: October 6, 1995, NLDS Game 3
No matter how many more of these happen moving forward, Mark Lewis will always be able to say he hit the first pinch-hit postseason grand slam ever. This dinger broke open NLDS Game 3 against the Los Angeles Dodgers — Lewis went deep in the sixth inning to extend Cincy’s lead to 7-1.
The Reds went on to win 10-1 to complete a three-game sweep of LA. This was the best moment Lewis had during limited postseason action. He participated in October baseball on two occasions (1995 and 1997), racking up 13 plate appearances across five games.
This pinch-hit slam was the only playoff dinger he recorded, and the four RBI accounted for two-thirds of his career postseason total (six). The infielder took advantage of his opportunities, though. Lewis owned a career slash line of .455/.538/.727 in October.
Ricky Ledée, New York Yankees
When: October 17, 1999, ALCS Game 4
Ricky Ledée’s pinch-hit grand slam also broke things open, extending the Yankees’ ALCS Game 4 lead to 9-2 in the ninth inning against the Boston Red Sox.
New York won the first two games before Boston blew them out in Game 3 by a score of 13-1. This slam made sure the Bombers took control of the series. They clinched the AL pennant in five games before winning their second of three consecutive World Series titles.
Ledée appeared in the 1998 and 1999 postseasons for the Bombers, producing an .860 OPS with one homer and 11 RBI across 80 plate appearances. He spent parts of 10 seasons in the big leagues and finished his career in New York in 2007, but it was with the Mets (and we all know that the ’07 season didn’t end in the playoffs for the Amazins).
Miguel Montero, Chicago Cubs
When: October 15, 2016, NLCS Game 1
Is there anything cooler than doing something that’s rarely been accomplished in MLB history as your team attempts to break a 108-year championship drought? I can’t be sure, but I think this is hard to top.
After getting past the San Francisco Giants in the NLDS, the Cubs went toe-to-toe with the Dodgers in the NLCS. Miguel Montero stepped up to the plate with the score tied at three in the eighth inning of Game 1 before making Wrigley Field erupt with the above dinger.
Once again, this was the only postseason home run of Montero’s career. He racked up 12 total plate appearances during Chicago’s 2016 title run, but this is the kind of moment that Cubs fans will remember for generations. Unlike the two before it, this one happened in the first game of a playoff matchup, which helped set the tone for Chicago.
The Cubs ultimately won the pennant in six games before winning the organization’s first World Series title since 1908.
Addison Barger, Toronto Blue Jays
When: October 24, 2025, World Series Game 1
Like Montero’s, this one came in Game 1 of a series. What sets it apart is that it’s the only one in World Series history.
It was part of an 11-4 victory for the Toronto Blue Jays, and while it gave them an upper hand early in their matchup with the Dodgers, Barger and Co. ultimately fell just short of hoisting the trophy in a tough seven-game series.
Barger slugged 21 homers with 74 RBI across 135 games in the 2025 regular season, and he relished his first taste of playoff baseball. In 68 postseason plate appearances, he slashed .367/.441/.583 with three homers, nine RBI, and eight runs scored.
The above grand slam was his only homer in the Fall Classic. While he drove in just one more run the rest of the series, Barger collected 12 total hits against Dodgers pitching, posting a 1.216 OPS in 28 plate appearances.
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