When will the White Sox and Cubs meet in the World Series? Sooner than you think

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White Sox fans had 11 years to hold their 2005 World Series title over the heads of their Cubs fan friends, but that ended with the North Siders’ curse-breaking championship last fall. Maybe you had to be in Chicago to sense it, but I definitely got the impression that was the worst part of the 2016 season for the Sox fan base.

There is one bit of bragging rights that the White Sox have held for much longer. In fact, it will be 111 years and counting by the time this season draws to a close. That is, the franchises have met in the World Series exactly one time, in 1906, and it was the White Sox who won that championship. Strange how you never hear that mic-dropped into friendly bar spats in Chicago. Where is the sense of history?

The avalanche of adoration that has showered the Cubs the past couple of years has left a lot of Sox fans feeling left out, kind of like Jan from “The Brady Bunch.” It didn’t help that the South Siders were one of the less interesting teams in baseball last season: not terrible, not contenders, with a long-term prospectus of paddling right down the middle for the foreseeable future.

However, White Sox general manager Rick Hahn flipped the script last winter, when he embarked on a rapid-fire rebuilding project that has given his organization one of the top farm systems in baseball. It has been a stunningly fast turnaround that plenty are comparing to the pivot the Cubs made a few years ago when Theo Epstein and Jed Hoyer arrived in town. The White Sox version feels like it is unfolding even faster than the Epstein rebuild, which included not just an overhaul of talent but also a complete rewriting of every baseball-related system in the Cubs organization, from Mesa to Wrigleyville. Before the 2016 season, ESPN’s Keith Law ranked the ChiSox system at No. 22 — and that was an improvement. It is now ranked second overall.

Consider this: Law ranked the Cubs’ system No. 20 during the winter before the 2011 season. After that season, Epstein was hired, and in the next set of winter rankings, the Cubs were still at No. 20. By 2013, the Cubs were up to No. 5, then No. 4 in 2014. In 2015, they were in the postseason, and in 2016, they were the champs.

The benefit of such a rapid rise is that everyone assumes the Cubs will be in the World Series mix for at least a few years, if only because so many of their core talents are under team control for the near term. The exact number of years in that window is hard to pin down, but it should be open at least through Kris Bryant’s last arbitration year (2021) and even beyond that if Bryant signs a deal to buy out those years. Of course, the window could be open much longer; this is a smartly run team with vast resources.

Now, let’s turn our attention back to the White Sox and prepare for a leap of imagination. First, we have to acknowledge that there’s a long way to go from where they are right now to where they want to be, which is in the same elite tier as the Cubs. Lofty prospect rankings are great, but they do not always add up to World Series contention.

Prospects get injured or fizzle out. Some organizations prove to be better at identifying talent than developing it. All sorts of things could go wrong.

With those qualifications out of the way, let’s pose this question: Could the White Sox contend for an American League pennant while the Cubs’ window of contention remains open in the National League? If so, when will we see the first Windy City Series since the days of Theodore Roosevelt?


A little history

Chicago was founded in 1833 with a population fewer than that of the South Loop building where I now live. Then the city was built up, burned down and built up again. Somewhere along the way, they started playing baseball. In 1906, when the White Sox played about five blocks south of where Guaranteed Rate Field stands now, the Cubs played on the city’s west side. As such, their World Series meeting was a West-South affair, which frankly doesn’t have the same ring to it as North-South.

Since that long-ago meeting, when the Hitless Wonders toppled a Cubs powerhouse outfit that had won 116 regular-season games, there have been remarkably few seasons in which both franchises were prime contenders in their respective leagues. In fact, there have been only 25 seasons since 1901 in which both were at least .500 — a rate of once every 4.68 years.

During the pre-divisional era, there were a few scattered seasons in which both teams finished in the top three of their leagues, but usually one of the two ended the season with a double-digit-game deficit to the pennant winner. After the major leagues’ split into divisions, there were a handful of seasons in which a Windy City series seemed at least possible:

  • 1972: The Cubs finished a distant second, 11 games behind Roberto Clemente’s Pirates. The White Sox also finished second, 5.5 games behind the eventual-champion Oakland A’s. The Cubs were never really in it that season, but it’s fun to muse over because the White Sox’s play-by-play guy in those days was Harry Caray.

  • 2003: The Cubs won the NL Central and came within a game of the pennant. We will not speak of why they fell short. The White Sox finished second in the AL Central that season, four games behind.

  • 2008: This was the closest we’ve come to a 1906 rematch. Both clubs won their respective divisions, and both flopped in the divisional series to go a combined 1-6. It was pretty while it lasted.


Back to the present

The Cubs’ timeline for winning has been scrutinized time and again, and the process through which they became a model franchise is one that other teams are scrambling to replicate. The bottom line: The rebuild wasn’t in effect, at least in terms of regular-season play, until the start of the 2012 season. They went on to lose 101 games. The Cubs made the postseason in 2015, after making their first major free-agent splurge to augment their young core with the signing of Jon Lester. They won the World Series in 2016, the fifth season of the rebuild.

That’s extraordinarily fast, but if Hahn and the White Sox can match that timeline, then we’re looking at the White Sox leaping into contention by 2020 and challenging for a title in 2021. That, if you recall, is the conservative estimate we put on the Cubs’ current window of elite contention.

Because the White Sox’s full collection of prospects is so new, it’s easy to envision how that might look — no one has washed out yet. At the big league level, Jose Abreu could still be viable by the 2020-21 seasons, though he might be a DH and veteran anchor. You could then be looking at Matt Davidson — or someone else, maybe a future splashy free agent — Yoan Moncada, Tim Anderson and 2017 first-rounder Jake Burger around the infield. Zack Collins, 2016’s first-rounder, could be behind the plate.

Some combination of Eloy Jimenez, Blake Rutherford and Luis Robert (or Charlie Tilson or Luis Basabe or Micker Adolfo) could man the outfield. The starting rotation might be stuffed with Michael Kopech, Lucas Giolito, Carlos Rodon, Reynaldo Lopez and Dylan Cease. There are other permutations and other prospects to come.

However, as Dave Cameron from FanGraphs noted, the White Sox have only entered into the talent-acquisition phase of rebuilding at this point, and for all the upside their young players have as a group, their results haven’t been particularly eye-popping. There’s a very good chance that the finished version of the future White Sox will be comprised of several names different from those listed above. That’s just how things go with developmental pipelines.

The Cubs have been lauded for their talent identification and acquisition efforts the past few years; all you have to do is look at who is on the field to see why. It has been an amazing turnaround from the beginning of this decade, and few teams have been so accomplished at such a collectively young age. But every bit as important as the acquisition phase has been the Cubs’ ability to transition their minor league studs into productive major leaguers.

The White Sox appear to be on track to match the Cubs in the first respect. But what about the second? That’s what we’ll find out over the next two or three years as they start to push all those young talents out of the prospect rankings and onto the major league roster.

If the White Sox do so successfully, we might be having a lot of fun in Chicago come the autumn of 2020 or 2021.



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