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Missed it by that much: Top five Yankees World Series matchups that never happened

Watching “The Last Dance” ESPN documentary miniseries on the Chicago Bulls, it got me thinking, what if Michael Jordan hadn’t retired and the Bulls played the Houston Rockets in 1993-94 and 1994-95? What would those series have looked like? Furthermore, has there ever been a championship series or game you wish had happened but one team didn’t fulfill its end of the bargain?

For instance, the stars never aligned for the Buffalo Bills and San Francisco 49ers to meet in the Super Bowl during the ’90s. Imagine the John Elway/TD Denver Broncos against the Randy Moss/Chris Carter Minnesota Vikings instead of the Atlanta Falcons or the St. Louis Rams “Greatest Show on Turf” against the Indianapolis Colts of Peyton Manning, Edgerrin James, Marvin Harrison, instead of the Tennesse Titans? I’m a New Jersey Devils fan but how cool would an “Original Six” matchup have been between the New York Rangers and Chicago Blackhawks been rather than the Los Angeles Kings? How about Hulk Hogan vs. Ric Flair in Wrestlemania VIII?

In baseball, there’s a fair amount of what-ifs too. The same holds true for the New York Yankees. So, what series did we miss out on?


Yes, the two teams locked horns in the 2003 Fall Classic. However, it’s not what I’m thinking of. The Yankees won the World Series in 1996 and the Florida Marlins won it in 1997. A matchup of the two stacked teams would’ve been epic in 1998. Yet, the Yankees won 125 games and the Marlins had a firesale. Speaking of 2003, how much cooler would a Yankees and Chicago Cubs World Series have been?

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They have met countless times but not in my lifetime and not since 1964. Recently the two clubs have been on the cusp but one or the other fell short in the LCS. Joe Torre’s ’96 Yankees could’ve taken on his old club and Tony LaRussa but St. Louis blew a 3-1 lead to the Atlanta Braves. We almost got it again in 2000 but the Subway Series was a nice “consolation prize.” It should’ve happened in 2004 but we won’t be discussing that. Both teams also lost in the 2012 LCS.

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Another matchup of teams that have met numerous times but not since 1962. They were on the cusp last decade but couldn’t quite get on the same page. New York finished off the aughts with a title in 2009. As a new decade dawned the Yankees nearly defended their title in 2010 but fell to the Texas Rangers, who lost to the San Francisco Giants in the Fall Classic. The Yankees fell short in the 2012 ALCS against the Detroit Tigers, who summarily lost to the Giants in the World Series.

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Not that having the best regular-season record in each respective league guarantees you anything but this matchup seemed to be on a collision course in 1994. Both the Yankees and Montreal Expos were on the rise, finishing second in their respective divisions in 1993. Each team had young brilliant managers in Buck Showalter and Felipe Alou. Don Mattingly homers off Pedro Martinez (oh hang onto the Olympic Stadium roof, Gary Thorne!) and the “who’s your daddy?” chants start a decade earlier. Alas, the strike meant no World Series that season. The two franchises also nearly met in 1981 and 2019 but we’ll address that next.

The 1994 World Series that could have been. | Sports on Earth


This classic matchup was the original Subway Series and turned into a bi-coastal affair. Yet, the two haven’t squared off in a World Series since 1981. We nearly saw a Joe Girardi vs. Joe Torre battle in 2009 but the Yankees won it that year with the Los Angeles Dodgers falling to the Philadelphia Phillies in the NLCS. In more recent vintage, the Dodgers earned the National League pennant in 2017 and 2018 but the Yankees and Yankee fans were cheated out of that classic matchup, twice! First, it was all of the Houston Astros and their cameras, laptops, and trash can banging, sign stealing in the 2017 ALCS (and likely again in 2019). Then it was the cheating Boston Red Sox and Alex Cora in the 2018 ALDS. The Yankees, Dodgers, and their fans were robbed of two consecutive Fall Classic faceoffs, 40 years after ’77-’78.

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(Honorable mention, I believe everyone wanted a rubber match between the Yankees and Red Sox in the 2005 ALCS but both teams lost in the ALDS that season).