#2 Worst: Cubs acquire Jose Quintana from White Sox for Eloy Jimenez and Dylan Cease
The Cubs gave a gift to their crosstown rivals in 2017 with a trade that gets worse by the day. In need of an excellent starting pitcher to bolster their rotation, they linked up with the White Sox to bring Jose Quintana over to Wrigley Field. He seemed like a potential ace at the time, coming off of three straight years of sub-3.50 ERA baseball while remaining incredibly durable, eclipsing the 200-inning mark in every year beyond his rookie campaign.
A player of that caliber, understandably, required a high price. The Cubs sent two of their top prospects, Eloy Jimenez and Dylan Cease to the South Side to reel in Quintana. Both prospects seemed redundant for the Cubs. They lacked a true spot for Jimenez with no DH and, since they were acquiring Quintana and already had Jon Lester and Kyle Hendricks around for a while, they could deal with losing Cease.
Unfortunately, Quintana wasn't the pitcher they hoped for at all. After pitching to a respectable 3.79 ERA the rest of the way with the Cubs in 2017, he'd struggle against the Dodgers in the postseason and never had an ERA below four again. Meanwhile, Jimenez would become an All-Star caliber bat with the White Sox, even if injuries would become an issue, and Cease would blossom into a Cy Young caliber arm, finishing second for the award in 2022. Oh, and he, too, is very durable. In an era where the Cubs needed an ace, they had to watch their former prospect become one in real time.
What makes this one all the more painful is who they COULD have had. Fans are well aware that Justin Verlander was on the market and had a desire to play on the North side. It's hard to blame the Cubs at the time for choosing the young, controllable pitcher, but it stung to see Verlander go on to post a 1.06 ERA in an Astros uniform and propel the team to their first, if tainted, World Series. He'd continue to age like a fine win in Houston too, winning two more Cy Youngs in 2019 and 2022.
Even if it meant losing Cease and Jimenez, having Verlander instead of Quintana for those few years after would've been a major consolation. Quintana was perfectly ok, but very far from what the team paid for.