The summer of 2017 found the Chicago Cubs in a strange and unsettling place. Just months after breaking a 108-year curse and winning the World Series, the glow of victory had faded into frustration. With a 43–45 record heading into the All-Star break, the Cubs trailed the surging Milwaukee Brewers by 5.5 games in the NL Central. The magic of 2016 felt distant.
On July 13, 2017, against this backdrop of mounting concern, the Cubs front office — led by President of Baseball Operations Theo Epstein — made a bold and surprising move. They orchestrated a rare trade with their crosstown rivals, the Chicago White Sox, acquiring left-handed starter José Quintana. While not a flashy blockbuster by name recognition, the deal reverberated through the baseball world. The shock came not from the pitcher’s resume, but from the stakes: an aggressive attempt to reignite a faltering title defense, the steep prospect cost, and the rarity of a trade between two bitter Chicago franchises.
Epstein and his team made the deal out of necessity. The rotation, once a pillar of the Cubs’ 2016 success, had deteriorated. John Lackey was showing serious signs of decline. Jake Arrieta, once dominant, had lost his edge. Even ace Jon Lester wasn’t the same. The fifth spot in the rotation had become a glaring weakness, especially after Brett Anderson’s disastrous stint, which ended with an 8.18 ERA and an injury. Meanwhile, the offense lacked rhythm. Losing leadoff man Dexter Fowler left a hole no one could fill—particularly not Kyle Schwarber, whose stint at the top of the order failed so badly he ended up in the minors. Across the board, the Cubs looked flat. They needed a shakeup.
The trade for Quintana was vintage Theo Epstein: sacrifice tomorrow’s potential to rescue today’s opportunity. His track record supported the approach. In 2016, he had traded elite prospect Gleyber Torres for a short-term rental of Aroldis Chapman to push the Cubs over the top. The Quintana deal followed the same principle. But unlike Chapman, Quintana wasn’t just a rental. He came with three-and-a-half years of team control at a bargain rate, a huge bonus given the looming free agency of both Arrieta and Lackey. Quintana was also durable—five straight seasons of 200+ innings and not a single missed start.
To land him, though, the Cubs emptied the top shelf of their farm system. They sent the White Sox outfielder Eloy Jiménez, their consensus top prospect and one of the top 10 in baseball, known for his explosive power and future star potential. Alongside him went Dylan Cease, the Cubs’ No. 2 prospect, a hard-throwing righty with electric stuff and top-100 rankings despite past Tommy John surgery. Two additional minor leaguers rounded out the package. It was a high price, but the Cubs were all-in.
At first, the gamble paid off. The Cubs returned from the break with a surge, going 14–3 and storming back into first place. Quintana dazzled in his debut, tossing seven shutout innings with 12 strikeouts. He remained steady down the stretch, posting a 3.74 ERA and helping lead the team back to the NLCS. If the trade was judged solely on the 2017 season, it was a success.
But over time, the outcome grew less favorable. Quintana never quite lived up to the cost. Across parts of four seasons with the Cubs, he posted a serviceable but underwhelming 4.24 ERA. He was good—but not the difference-maker they had hoped for.
Here’s the thing, folks: Cease developed into a frontline starter, finishing second in AL Cy Young voting in 2022. Jiménez, despite injuries, became the middle-of-the-order bat scouts had predicted, even earning a Silver Slugger award in 2020. In hindsight, the trade’s real damage was in what the Cubs lost: a future pipeline of cheap, elite talent.
With that… The deal wasn’t reckless — it was calculated and aligned with a win-now mindset. It’ll be interesting to see if Jed Hoyer, now President of Baseball Operations for the Cubs, tears apart the entire minor-league system he’s built at the deadline or fills one or two holes in preparation for next season when he may no longer be here.
If you cannot play with them, then root for them!