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Come Fan with UsSunday, June 21, 2026

What the Cubs were thinking with the Jose Quintana trade (and how they’d better be right)

The Cubs and White Sox pulled off a stunning trade out of nowhere. Here’s why.

Chicago White Sox v Colorado Rockies
Chicago White Sox v Colorado Rockies
Photo by Matthew Stockman/Getty Images

I regret to inform prospect-hugging Cubs fans that it was always going to be like this. This is the plan, at least in part. The Cubs were going to load up on hitters. Young hitters, fast hitters, power hitters, contact hitters, and in some cases, young, fast, power hitters who make great contact. And when they needed pitchers, they were going to buy them. Or trade for them.

Here’s a trade! Surprise! Good morning! The Cubs traded Eloy Gimenez, one of the best prospects in baseball, along with Dylan Cease, Matt Rose, and Bryant Flete for White Sox left-hander Jose Quintana. Depending on your thoughts on Yoan Moncada and Michael Kopech, you could argue that this was nearly as expensive as the Chris Sale trade.

It’s obvious what the Cubs are thinking. It’s obvious that it has to work. This isn’t their last bullet, but it’s a pretty big ammo dump for one pitcher.

What the Cubs were thinking

Win now. Win later. Quintana is just 28, and he’s signed for baseball peanuts through 2020. He’ll help the Cubs win this year, ostensibly, and Jimenez, Cease, Rose, and Flete will not. If/when Jake Arrieta and John Lackey leave in free agency, the Cubs will not have to pay a desperation tax. They will have at least three-fifths of their rotation figured out, and they can build from there.

That’s it. That’s what the Cubs were thinking. Win now, win later. Build around the young position players with a pitcher who should age gracefully and be inexpensive enough to the Cubs to buy more support in the free-agent market.

And while it cost them dearly with Jimenez, there was no obvious place for him to play in the near future.

The Cubs are young. Their rotation got better. They nabbed one of the lowest-cost rotation toppers on the market. This is a trade that helps them in 2018, even if they continue screwing up this year.

You can see what the Cubs were thinking.

How the Cubs are taking a wild risk and had better be right

Begin with Jimenez, who is 20 years old and absolutely compelling. There are prospects who pique your interest, and there are prospects who take the yoke of your imagination and fly it directly into the sun. Jimenez is one of the latter.

He was the one who Roy Hobbs’d the lights in a minor league home run derby just a couple of weeks ago:

And while it’s true that he didn’t really have a place to play with the Cubs’ Schwarber/Happ/Heyward permutation ... I mean, one of those outfielders is Jason Heyward ... you don’t ditch your best prospects because you’re not sure how they’ll fit in with a defense-first outfielder. That’s not to mention that the other corner is filled with someone who was hitting so poorly that he had to take a detour to Triple-A for a bit.

These things are fluid, always. The Cubs outfield in 2019 might be Jacob Hannemann, Charcer Burks, and Matt Joyce for reasons you can’t possibly comprehend right now, and they might wistfully sigh whenever the wind whispers “Eloy.”

Now move to the idea that Quintana is in the middle of an enigmatic season. I’ve been paddling my canoe through the choppy waters of hot-take Twitter, and there are people who are mad that Quintana has a 4.49 ERA, and there are people who are mad at those people because the strikeouts are still strong and the previous six seasons mean a lot more than the first couple of months of the season, and there are people mad at those people, et cetera. But we can all agree that Quintana’s season has been confusing.

After allowing a combined 15 runs in back-to-back starts at the end of May, Quintana has a 2.70 ERA in seven starts, walking 16 and striking out 45 in 40 innings. That’s the good news. But the bad news is that he’s thrown more than 5 1/3 innings in just three of those seven starts. While the runs have been prevented, they haven’t been prevented very efficiently.

I am very much Team Six Years compared to Team Three Months. Quintana is young, and he’s been excellent far longer than he’s been mysterious. The Cubs are trusting their scouts, and that strategy paid off with a World Series last year.

On the other hand, I’m also wary of any pitcher who starts to struggle in this new, uncharted era of the low seams. While Quintana’s struggles aren’t explicitly tied to an increased home run rate (although it is the highest of his career), I’m far less comfortable with the idea that a pitcher will reclaim his success just because he had success to begin with. The walk rate is most certainly up. The efficiency is down. It could be a blip, but what if it isn’t?

But what if it isn’t? Yipes. It’s scary enough to trade a prospect like Jimenez (and Cease) for an ace in the middle of a great season. It’s extra scary to send him off for an enigma who’s probably fine, definitely, totally, maybe, I hope.

And after acknowledging the potential of Jimenez and concern-trolling a bit with Quintana, you get to the part that if this trade blows up, the evidence will be staring Cubs fans directly in the face from a couple of miles away. It was always a silly notion that the Cubs and White Sox wouldn’t deal with each other, but that doesn’t mean the extra shame and regret from a failed trade isn’t real.

I get why the Cubs did the deal. I get why Cubs fans are nervous as all heck. And I also don’t quite understand how the White Sox were able to get as much as they could have for Quintana as they would have if they dealt him in the offseason, as if the last three months never happened, and I applaud their efforts.

Jose Quintana is on the Cubs now. It’s sensible and terrifying at the same time, and it had better work out. For all sorts of reasons.

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