The leaves are changing colors, and the temperature is beginning to drop. The Bears battle for the NFC North crown is entering it’s seventh week, while the Hawks and Bulls are just beginning their respective journeys. October is a special time in Chicago, but for the first time in three years, fans of the city’s south and north side teams are watching other baseball teams compete deep into October.
For White Sox fans, a postseason of watching other teams celebrate has become commonplace. The team has not made the made the playoffs since 2008, and just wrapped up it’s first 100 loss season since 1970. But for Cubs fans, an empty October is a strange feeling. Cubs fans may still shell shocked by the team’s demise. Watching a five game September division lead turned into a gut wrenching Wild Card game loss to the Colorado Rockies. Regardless of the reasons why neither team is in the playoffs, it’s an empty feeling in Chicago without baseball in October.
Watching the playoffs from home isn’t the only similarity the Cubs and White Sox share this offseason. Both teams have reached a crossroads for their franchises. For the Cubs, what once seemed like an heir apparent dynasty to the Blackhawks, has turned into a team that despite 95 wins, is now facing major questions about their core, farm system, and coaching staff after a disappointing collapse to end the 2018 season. For the White Sox, the shine has worn off of the rebuild, and overwhelming hope has turned into creeping anxiety, as top prospects such as Yoan Moncada and Lucas Giolito have failed to look the part of future center pieces. The White Sox most exciting major league piece, the electrifying Michael Kopech, pitched in only four games before tearing his UCL, sidelining him for the 2019 season.
Both teams are facing immense pressure from fan bases and media critics alike. “Show us results” fan bases cry to Theo Epstein and Rick Hahn. Cubs fans have grown tired of waiting for players such as Kyle Schwarber and Ian Happ to step up and turn into the superstars they were billed as. Addison Russell, the former top prospect and World Series hero compounded an already disappointing 2018 season with domestic abuse allegations that will sideline him for the first 30 games of the 2019 season, wherever his 2019 season may take place.
For Rick Hahn and Theo Epstein, this is where the hard part of their job begins. Two years ago, Epstein was still freshly basking in the glow of ending the Cubs infamous World Series drought, and Rick Hahn had just kickstarted what appeared to be most promising rebuild in baseball. Their faces were put on t-shirts for fans, and those same fans cheered and pulled out cameras when they would see the two executives on the street. They were rockstars, but that is no longer the prevailing feeling along the eight miles that separate the two teams.
For Hahn, he has proven he has what it takes to tear down a team and rebuild a lacking farm system, but he now faces the first offseason of his career where he must prove he has what it takes to build a team into a champion. Epstein has proven that he can build a champion, but he must now prove that he learned from his mistakes that prevented the Red Sox from winning another title until long after he had left, and the team had endured a brief rebuild.
While the goal for Epstein is to build a champion, and the goal for Hahn is to build a team that just competes, both teams face similarly unpleasant uncertainty as they enter their respective off-seasons. The free agent market offers no easy solutions. Beyond Manny Machado and Bryce harper, there are no players on the free agent market that represent a significant upgrade for either team. Both teams will be in on the big free agent names, but perhaps equally as important for both teams are the potential upgrades the free agent market possess for both teams pitching staffs. Dallas Keuchel and Patrick Corbin represent potential fixes for both teams rotations, but both fan bases are ambivalent about giving either pitcher the large contract they will likely require. After those two, the market offers some intriguing, but not game changing options. One of those pitchers would likely represent a fair upgrade for the White Sox rotation, but for the Cubs, who hope to be riding double decker busses to Grant Park in November, none of those options likely cures what ailed them as the 2018 season turned from thrilling to forgettable. Theo Epstein will be facing particularly intense scrutiny on his free agent moves after whiffing on his three big signings a year ago.
What about the two big fish? The White Sox have not been discreet in their lust for shortstop Manny Machado.They possess the financial flexibility to get the deal done, but can they offer Machado an enticing enough situation? For the Cubs, big contracts to Jason Heyward, Yu Darvish and Jon Lester may make signing one of Harper or Machado difficult, but they are always a team to watch for in the free agent market.
On the trade market, both teams face difficult decisions on familiar faces. The Cubs have reached a crossroads in respects to Ian happ, Kyle Schwarber, Albert Almora Jr, and Addison Russell. Two or more of those players are likely on their way out of Chicago, as the Cubs prepare to commence the closest thing this roster has seen to an overhaul in nearly five years. The White Sox face a decision on slugger Jose Abreu, who will be entering the last year of his contract in 2019. Will the White Sox look to extend the fan favorite, or will they attempt to harvest any value they can get out of him on the trade market. The team also faces a tough decision with Carlos Rodon. Who after returning from the disabled list in June, looked the part of an ace until a rocky September ended his season on a sour note. Much like the Cubs, many familiar faces could potentially have played their last games on the South Side.
It is rare that both Chicago baseball teams face potentially franchise altering off-seasons at the same time. Yet here we sit, in an October with no baseball, wondering if long off-seasons are back in style in Chicago or if this the off-season where both teams manage to place themselves among baseball’s elite. Only time will tell, but for better or for worse, fans will likely look back at the 2018-2019 off-season as one of Chicago’s most pivotal.
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