Chicago Cubs can’t help but play ‘what if’ after Tuesday night’s loss

The mid-2017 blockbuster that brought Jose Quintana to the Chicago Cubs and sent the team’s top two prospects to the South Side took center stage Tuesday.

Looking back and evaluating the 2017 All-Star Break blockbuster between the crosstown rival Chicago Cubs and Chicago White Sox is no easy task. The fans and the media of course always want to be quick to crown a winner and pinpoint a loser but sometimes it isn’t always as clear-cut as we may like.

In this case, both teams were on completely different trajectories and looking to accomplish different things. The Cubs were coming off a World Series title in 2016 and their championship window was, for all intents and purposes, wide open. Meanwhile, the White Sox were in complete rebuild mode, selling off their most talented pieces in order to stockpile prospects to form the best farm system in all baseball.

Now, with these two teams being crosstown rivals, they almost never make any deals. In fact, prior to the Quintana trade, the clubs hadn’t made a deal since 2006. But they came up with a trade that, at the time, really benefited both teams.

The Cubs parted ways with their top prospect in Eloy Jimenez, Dylan Cease, Matt Rose and Bryant Flete in order to acquire Jose Quintana from the White Sox. The Sox got the highly-touted prospects they so highly coveted in Jimenez and Cease and in return the Cubs got a third dominant starting pitcher in Quintana to go along with Jon Lester and Kyle Hendricks in the rotation.