Tuesday Morning Thoughts: How likely is another Crosstown Trade?

For most of the 2000s and into the 2010s, trades between the Chicago White Sox and Chicago Cubs were rare. Although the two teams had made deals in the past, exchanging such notable players such as Sammy Sosa and Jon Garland, neither team was in the habit or pursing deals with the other — especially high-profile ones.

That changed in July of 2017 when Rick Hahn and Theo Epstein struck a blockbuster deal, sending White Sox ace Jose Quintana to the North Side for a package including blue-chip prospects Eloy Jiménez and Dylan Cease.

Five years later, the White Sox have been the clear-cut winner of the deal. The Cubs received very little production out of Quintana, who never recorded an ERA below 4 in parts of four seasons. Meanwhile, Cease looks like a surefire Cy Young candidate, and Jiménez, when healthy, is a legitimate power source in the middle of the White Sox lineup.

Last summer, the tables turned. This time, it was the Cubs apparently fleecing the White Sox, sending Craig Kimbrel to the South Side in exchange for Nick Madrigal and Codi Heuer. Kimbrel’s stint on the South Side was wildly unsuccessful, failing to get into any sort of a rhythm in a set-up role before being dealt for AJ Pollock this March.

Madrigal has struggled to start his first season with the Cubs, and Heuer is out until next season with Tommy John surgery, but the Cubs received a pair of pieces who could play large roles on the next series of winning Cubs teams, while the White Sox have a massive hole at second base for the foreseeable future.

The White Sox and Cubs are off to similar starts this season — both 9-13 through their first 22 games. The Cubs weren’t necessarily expected to compete this season, but the early play of rookie phenom Seiya Suzuki and a better-than-advertised pitching staff have kept the North Siders afloat.

The White Sox were expected to compete, and they have not. It’s early, and they’re still getting healthy, but in a month or so, the White Sox will seriously need to look into making improvements to the current major league roster before falling too far behind in the standings.

The Cubs could certainly offer the White Sox some pieces of interest. One name that stands out on the Cubs is Ian Happ. Happ is the team’s starting left fielder, but can play all three outfield positions and second base — a flexibility that immediately makes him a perfect fit for the White Sox.

Happ is also off to a great start this season, hitting .303 with two home runs and a .859 OPS while playing in all but one Cubs game to this point. He has one more year of control and is a key contributor in the Cubs lineup, so he certainly would come with a price. Unless that price is, say, Oscar Colás, Colson Montgomery, or Norge Vera, it’s a price that the White Sox should be willing to pay.

Another area of the roster where the White Sox could seek reinforcements from the Cubs is the bullpen. The Cubs signed a slew of veteran relievers to short-term contracts this past offseason, including Chris Martin, Mychal Givens, and former White Sox closer David Robertson. While the back end of the White Sox bullpen looks pretty sharp, you can never have too much pitching, and odds are the White Sox will need it come deadline time.

If the White Sox can get back to their winning ways, we could very well see another deal with the Cubs in July. Last summer saw a pair of deals between the two teams — one major and one less so — so the connection is there.

Let’s just hope the White Sox don’t screw up as badly this time around.