The New York Yankees’ greatness can be measured and appreciated in many different stats; one of them is that at some point or another, they’ve played at least one playoff series against 26 of the other 29 active teams in Major League Baseball, eye-popping even for a team with 27 World Series titles and 41 pennants to its name. Surprisingly, not all three exceptions are members of the National League—that is the case for the Colorado Rockies and Washington Nationals, but the third one resides on the South
Side of Chicago, a 1901 founding member of the American League that predates the Yankees themselves. One might excuse expansion teams such as the Texas Rangers and Tampa Bay Rays for not featuring in this contingent, but for the Chicago White Sox to be a part of this select group, that’s just strange.
Beginning a weeklong homestand this week, the Yankees host the White Sox in a rare battle—particularly over the last few seasons—of these two teams both fighting for division leads. Just as the Yankees overtook the Rays, the White Sox fell to even with the less surprising Cleveland Guardians. While it is far too early to be certain of the Pale Hose sustaining this level of play as a legitimate threat to make the postseason, their current presence in the hunt and upcoming matchup with the Yankees provide the ideal segue to discuss the history, or in this case, lack thereof, between them.
For well over a century, the Yankees’ success has been as close to a constant as any team could get, and thus, the reality of assessing never-before-seen playoff matchups involving them leaves the responsibility entirely on the other side. It’s the Rockies’ fault for only making one Fall Classic in their history, and the same applies to the Nationals. And even then, the Yankees could’ve easily faced one of the two with better luck in the 2007 or particularly the 2019 postseason. If we want to include the Montreal Expos as part of the Nats’ history, they fell just two runs short of a showdown with New York in 1981 after losing to the Dodgers in a winner-take-all NLCS Game 5.
Around for far longer than those two aforementioned NL clubs, the White Sox playoff history is equally lacking given its context, with Chicago having played in a total of 11 postseasons dating back to 1901. It is a staggeringly low total for a team with 125 years of history. Out of those 11 appearances, four came prior to the existence of divisional play and postseason series in each league, with Chicago advancing straight to the Fall Classic in 1906, 1917, 1919, and 1959.
Here we’ll note that if said divisional play had been introduced earlier in the ’50s or ’60s, perhaps the Yanks and White Sox would have gone head-to-head in an American League Championship Series. Modern fans might not realize that those White Sox were quite competitive with the dynastic Yankees between 1952-64, but finished third six times and runner-up on four occasions. The Yankees were also third during Chicago’s lone pennant-winning season in 1959.
So we move on to 1969 and the beginning of the ALCS. The Yankees have never shared a division with the White Sox, who were quickly sorted into the AL West prior to the existence of the AL Central. A playoff matchup was possible! But they were rarely contenders at the same time. The White Sox won two AL West crowns, in 1983 and 1993. Both came during the Yankees’ 14-year playoff drought. Another White Sox division title in 2008 arrived in conjunction with New York’s run of 13 consecutive postseason appearances coming to a close.
We’re left with only four occasions in MLB history when both these teams made the playoffs.
Through one of the postseason’s most impressive runs back in 2005—when they won the championship, losing only one game across three playoff series—the White Sox nearly had the Yankees in their way, but New York faltered in the do-or-die Game 5 of the ALDS against the Angels. Whatever one’s feelings are regarding that 2005 Yankees team, they probably could’ve offered the Sox a bigger challenge than the Angels, who lost four straight after winning Game 1, seeing the elder Vladimir Guerrero wrap up that series with a 1-for-20 line. There is also an alternative path: if the Red Sox had finished ahead of the Yankees in the standings (both teams finished with the same record and the Yanks won the division on an off-field tiebreaker) the Yankees would’ve been the ones matching up with the Pale Hose in the ALDS.
While the Yankees didn’t get a chance to run into the eventual champs in 2005, the opposite was the case a few years prior in 2000. The American League’s top seed in that season, the White Sox were swept by the Mariners, a turn of events that handed the Yankees home-field advantage in that year’s ALCS against the Alex Rodriguez-led Seattle club. Despite having the worst record, the Yankees got the edge as division winners on their way to winning the Fall Classic.
Decades later, while the 2021 campaign didn’t present a particularly close possibility given that the Yankees lost the Wild Card Game to the Red Sox and the White Sox were on the other end of the bracket, scheduled for an ALDS matchup against the powerhouse Astros (one that they lost in a gentleman’s sweep), the 2020 campaign tells a more interesting story.
The way seeding worked in the shortened 2020 campaign with each of the three divisions guaranteed at least two playoff teams, meant that even though Cleveland and Chicago finished with the same record, Cleveland, which had the tiebreaker, secured the fourth seed, while the ChiSox had the seventh seed. Had the White Sox finished ahead of Cleveland, they would’ve played the five-seed Yankees, who actually had a worse record than both. Instead, Chicago lost to Oakland in the first round, and that was that.
To this day, the 2020 through 2021 period is the only one in which both the Yankees and White Sox made the playoffs simultaneously in consecutive years. Unfortunately for Chicago, things spiraled miserably for their window of contention after that, and 2026 is the first year with signs of life since then.
Lastly, with the possibility of a lockout looming, we’d be remiss not to touch on what transpired in the 1994 campaign, another one with unfulfilled potential for a Yankees-White Sox playoff series. When play stopped, the Yankees and White Sox were the top two teams in the American League. Cleveland was chasing Chicago, only a game back, but even if they managed to pass the White Sox, it would only turn a likely ALCS matchup into a certain ALDS one. While the Yankees went on to dominate the second half of the ’90s, the White Sox didn’t get back to the postseason until 2000, leading to several lean years wasting the prime of Frank Thomas.
This won’t go on forever. Remember, the Yankees had never played the Blue Jays in the postseason until last year either. The deck of cards metaphorically representing an MLB season will eventually deal us a Yankees/White Sox playoff matchup — it could even happen in 2026 if both sides keep up the good work. May the Ron Hassey Bowl one day come to pass.
