EmailPrintOpen Extended ReactionsWhen the Chicago White Sox and Chicago Cubs take the field Monday at Wrigley Field, they'll both do so as World Series contenders, in the sense that any team that lands a spot in October has a shot at the Fall Classic.The venerable Chicago rivals being title contenders in the same year hasn't happened often throughout history. In fact, you can count on one hand how many times we've seen better odds for the long-awaited rematch of the 1906 World Series -- and you would not need to deploy your thumb while counting.As a Chicago-based baseball writer, I could not help but notice near the end of June that no matter which ballpark I went to, Rate Field or Wrigley, I was checking out a contending team. (It's those astute observational abilities that are the mark of a true professional.)It was around that time when I created a new tab in my tracking system that had one function: to grab the results from my daily season simulations, count how many times the Cubs and White Sox met in the World Series via those sims and then keep those results in a daily log.When the clubs meet to start a three-game, mid-August series, whether they know it or not, the chances they will be taking part in a Windy City World Series preview are about 63-to-1. Those odds, kicked out by my simulations, have ebbed and flowed as the daily standings and power ratings fluctuate, but the deeper we've gotten into the season, the overall trajectory has been steadfastly positive. Even at this apex, the odds are pretty long, but for most of modern baseball history, they've been much longer.As I watched those odds evolve each day, I could not help but wonder how many times both Chicago teams have been postseason contenders this deep into the same season, especially with this week's last regular-season North Side-South Side showdown looming.Using Monday's date (Aug. 17) as my guide, I leveraged the always miraculous Baseball Reference and entered the win-loss record, games behind for the division and overall playoff races, pennant chances (per Baseball Reference's archive of playoff odds) and title odds as of this date for both Chicago teams for every season, dating back to the founding of the South Siders in 1901.Initial findingsI used a cutoff of five games behind or fewer from a playoff slot as a flag for each White Sox or Cubs contender (as of Aug. 17 each season) and created a bucket of snapshots of the 126 seasons going back to 1901, which is also the period commonly known in baseball history as the modern era:Windy City: The wind is blowing for both teams in the city. There have been only 11 such seasons of dual-contention during the era (9%).South Side: White Sox are contending, but the Cubs aren't. There have been 29 of those seasons (23%).North Side: Cubs are contending, but the White Sox aren't. There have been 32 of those seasons (25%).Bears: Chicago fans are getting eager for football season, because neither baseball club is getting it done. And yeah, some of these seasons fell during the period before the Bears or the NFL was around, but you get the feeling that a lot of Chicago fans were probably waiting on the Bears anyway. There have been 54 of those seasons (43%).There have been just three instances of back-to-back years of dual-contention. The first started with the 1906 Wind City World Series, followed by 1907. Then, it didn't happen again for nearly 100 years, at least not this far into a season. Then, it happened twice in six years: 2003-2004 and 2008-2009.This is a well-known fact, but it's worth restating: The Cubs and White Sox have both made the postseason just three times -- 1906, 2008 and 2020 (shortened season).Somehow, 1906 is the only year on record in which the Cubs and White Sox were in first place on Aug. 17. Additionally, both clubs finished in first place in 2008.The furthest from contention for both teams combined occurred in 1942, when the Cubs reached Aug. 17 at 28 games out of first place and the White Sox trailed by 25 -- a combined 53 games back. Luckily, the Bears were not only around by then to distract from the misery, but Sid Luckman and Co. went undefeated during the 1942 NFL regular season.Seasons with the best Windy City World Series oddsHere are the 10 seasons with the best odds, as of Aug. 17, to culminate in a Windy City World Series -- with a brief explanation for why the top six showdowns did not come to pass and the one time it did.1907: 2.8-to-1 odds of a Windy City World SeriesAug. 17 snapshot:White Sox: 64-45, one game behind Philadelphia in AL (36.1% pennant probability)Cubs: 78-29, 14 games ahead of New York in NL (99.9% pennant probability)The best Aug. 17 odds for an All-Chicago series did not occur the year it actually happened, but the year after. The Cubs were in the midst of one of the great multiyear runs by any team and went on to beat Ty Cobb and the Detroit Tigers in the 1907 World Series, the first of back-to-back titles for the then-West Siders.The White Sox, no better on offense than the famed Hitless Wonders of the season before, were in the midst of a four-team scrum in the AL and were just a game back on Sept. 24. But Chicago dropped six of its last nine, helping propel Cobb to his first World Series.1906: 3.3-to-1 odds of a Windy City World SeriesAug. 17 SnapshotWhite Sox: 63-43, 1 games ahead of Philadelphia in AL (31.2% pennant probability)Cubs: 77-30, seven games ahead of New York in NL (97.2% pennant probability)The Cubs set the modern record for wins in a season in 1906 by going 116-36, a win total that was not matched until Seattle did it in 2001. Meanwhile, the White Sox rode a 2.13 ERA to the AL pennant. By the time the clubs clashed in the World Series, both were on fire. The Cubs went on a 48-6 scorcher to end the season, while the White Sox went on an 18-game run, beginning in early August, and held off New York, Philadelphia and Cleveland to win the AL.Thus, Chicagoans in 1906 got to see the one, and only, Windy City World Series, which was won by the South Siders in a massive six-game upset. One legacy of those record-setting Cubs, as with the 2001 Seattle Mariners team that tied their mark: A 116-win season did not end with a championship.2008: 19.2-to-1 odds of a Windy City World SeriesAug. 17 SnapshotWhite Sox: 69-54, half a game behind Minnesota in AL Central (13.5% pennant probability)Cubs: 75-48, 4 games ahead of Milwaukee in NL Central (38.5% pennant probability)This feels recent but, dang, it has been 18 years. It was long enough ago that a rookie who appeared for the White Sox that season is now their current general manager, Chris Getz. He got into only 10 games, but the White Sox won nine of them. He made his big league debut on April 28 by pinch running for Paul Konerko. Also coming off the bench in that game for the White Sox: Ken Griffey Jr. Yeah, it has been a minute.The White Sox were three years removed from ending their title drought in 2005 and seemed well-positioned to make another run at it, even as the Cubs were mounting a charge on the North Side. Alas, the ChiSox had a losing September. They still held on to their AL Central lead, but fell in a four-game ALDS loss to Joe Madden's Tampa Bay Rays.The Lou Piniella-led Cubs moved into first place on May 11 and stayed there the rest of the regular season. In addition to the buzz of a possible all-Chicago World Series, many had visions of a Wrigley Field-Fenway Park Fall Classic after the Boston Red Sox reached the playoffs with 95 wins in the AL. Instead, the Cubs were outscored 20-6 while getting swept by the Los Angeles Dodgers in the NLDS.So rather than capitalizing on the best Windy City World Series chances in 101 years, the Cubs and White Sox went a combined 1-6 while falling short of LCS appearances.1945: 41.3-to-1 odds of a Windy City World SeriesAug. 17 SnapshotWhite Sox: 57-50, 5 games behind Detroit in AL (2.9% pennant probability)Cubs: 70-39, 4 games ahead of St. Louis in NL (83.4% pennant probability)The front-running Cubs cruised to the NL pennant, their last one until 2016. Stan Hack, Phil Cavarretta and Andy Pafko were among those who carved out legacies as beloved Cubs for being on what, for a long time, felt as though the North Side's last pennant winner.Few remember or even know that the White Sox mounted a run that season as well. It was a nondescript group that was cobbled together during World War II. The most famous name on the roster -- Luke Appling -- played only 18 games. As it was, Aug. 17 was the crest of that particular Sox wave. It fell back from there, and the ChiSox finished well under .500.One thing to keep in mind about pre-1969 probabilities is that there was only the World Series. You finish first, you're there. Thus, that drives up the odds a bit for teams in those years, if they were in the vicinity of contention. But even in that context, the White Sox and Cubs seldom were in it during the same year.2026: 63-to-1 odds of a Windy City World SeriesAug. 17 SnapshotWhite Sox: 65-58, 5 games ahead of Detroit in AL Central (13.7% pennant probability)Cubs: 72-53, 5 games behind Milwaukee in NL Central (12.7% pennant probability)The White Sox's chances to win the AL passed the Cubs' pennant chances in the NL over the weekend thanks to their crucial three-game sweep in Detroit. Meanwhile, the Cubs dropped two of three at home to St. Louis.The White Sox beat the Cubs in two out of three in May, the series clincher coming on a spine-tingling extra-inning homer by Edgar Quero. That was the second loss in what became a 10-game skid for the previously rolling Cubs. Meanwhile, the win was a high point for a young White Sox club just taking flight.The Cubs have played better baseball since then for the most part, while the White Sox have remained just a few games above .500 at any given time. But the largess of the AL has kept the ChiSox not just atop their division, but with a tenuous hold on a first-round bye. However the paths have differed, both teams arrive at this series with bigger designs than taking the next crosstown installment.1984: 156.7-to-1 odds of a Windy City World SeriesAug. 17 SnapshotWhite Sox: 58-61, 4 games behind Minnesota in AL West (2% pennant probability)Cubs: 70-50, 2 games ahead of New York in NL East (31.9% pennant probability)As you can see, the odds are already tilting upward. The 1984 Cubs are one of the most beloved editions in franchise history, led by MVP Ryne Sandberg, Cy Young winner Rick Sutcliffe and (spiritually) by a hyped-up Harry Caray. This was really the beginning of the Cubs' brand as we've come to know it, at least as a national phenomenon.By comparison, the White Sox, coming off a division title in 1983, were lost in the shuffle, and probably should have been. Tony LaRussa's crew was never anything more than a fringe contender before falling apart after the All-Star break. They were only 1 games back on Aug. 9 but went 17-32 the rest of the way.The other four seasons1915: 222.8-to-12004: 275.7-to-11977: 416.7-to-11996: 552.5-to-1That rounds out the top 10, and, as you can see, we're talking long odds. It underscores the point that this season's level of dual-contention in Chicago is rare and worth savoring.Of those last four seasons, the one I'd highlight is 1977 because it typifies how so many seasons have gone for Chicago baseball fans over the eons.On the north side, the '77 Cubs began the season almost inexplicably hot. The team featured a below-replacement version of Bill Buckner, an aging Bobby Murcer, workhorse starter Rick Reuschel and Hall of Fame closer Bruce Sutter, who had his best season that year. Really, Herman Franks' club had no business contending. At the end of an eight-game winning streak on June 28, the Cubs were 47-22, and Baseball Reference had them with a 77% shot to make the playoffs and a 33% chance to win the pennant. They finished 81-81.That selfsame summer was the long-remembered time of the South Side Hitmen (in retrospect, not a great nickname), with Bill Veeck watching in rapture as Richie Zisk, Oscar Gamble and Eric Soderholm were among those slugging the White Sox into first place. They led the AL West by as many as 5 games and as late as Aug. 14. The White Sox finished 12 games behind Kansas City.At the All-Star break that year, the Cubs and White Sox held first place. A Windy City World Series felt like a real possibility. Within a month, those odds had already grown long, then they dissipated.That has been the story for most of the few seasons in which the Cubs and White Sox have been good at the same time. Will that be the case this season? We can't know. All we know, Chicago fans, is you better enjoy it while you can.
