The Cubs and the White Sox. Crosstown rivals. One with World Series aspirations, the other trying to figure out which pieces will be around for their next playoff run. The Cubs will be sellers at 18 games below .500 at this season’s trade deadline. The only question for them is who stays and who goes?

On the Southside, the White Sox had the third-highest preseason odds to win the World Series. Their season has been riddled with injuries, slow starts, and questionable decision-making by Hall of Fame head coach Tony LaRussa. Intentionally walking one of the fastest players in baseball, Trea Turner of the L.A. Dodgers, on a 1-2 count drew criticism for LaRussa around the league. Blunders and questionable lineup decisions aside, the White Sox are only 5.5 games back in the Central Division (behind the Guardians and Twins.) They’re also 5.5 games back in the Wild Card race with more than half the season still to play. So they have time. On paper, they should have enough offensive firepower too. Jose Abreau, Luis Robert, and Yoan Moncada have a history of heating up when the weather is hottest. With injuries mounting, the Southsiders could use a shot in the arm – one that their crosstown rivals might be able to give them.

A History of Cubs/White Sox Trades

Up until a few years ago, crosstown trades were taboo. The clubs stayed out of each other’s back yards — and before interleague play began in 1997 — only had one notable trade together. Thirty years ago, the White Sox sent 23-year-old Sammy Sosa to the Cubs in exchange for George Bell. The White Sox were gearing up for a World Series run (sound familiar), one that would get squashed by the 1994 lockout. Sosa began his Cubs career as a Gold Glove-winning outfielder and 30/30 player (home runs & steals). Then in the 1998 season, Sosa and Mark McGwire put baseball back on the map for millions of Americans as they went neck to neck chasing and eventually breaking Roger Maris’ home run record. Sosa is still the only player in Major League Baseball history to hit 60 home runs in three seasons. The Cubbies won that trade.

#OTD in 1992, the #Cubs acquired Sammy Sosa in a trade with the White Sox for George Bell. pic.twitter.com/TH7XObQtNq

— Cubs Talk (@NBCSCubs) March 30, 2020

Cubs/White Sox Trades: The Modern Era

After the Sosa trade, Cubs/Sox trades stalled for nearly 25 years. Not until 2017 did the Chicago franchises pull off another trade with such significance – one that would net the White Sox two foundational pieces in their hunt for another World Series.

White Sox Put Rebuild Into Overdrive with Jose Quintana Trade

Flash forward to 2017. The White Sox playoff window had closed. All-Star Chris Sale had already been shipped to the Red Sox. The White Sox were in the midst of a full-blown rebuild. Lefty Jose Quintana had been a staple in the White Sox rotation, regularly winning ten or more games with an ERA under 4. He was also under contract for another season – making him one of the hottest trade deadline targets. The Cubs were coming off their first World Series win in 108 years. They had a young core including Anthony Rizzo, Kris Bryant, Javy Baez, Willson Contreras, and Kyle Schwarber and were looking to repeat. The two teams were going in opposite directions and became perfect trade partners. The White Sox shipped Quintana to the Cubs for their top two prospects, Eloy Jiminez and Dylan Cease. It would take a few years, but both players are now critical pieces for the White Sox. Jiminez hit 30 home runs in 2019. His future is probably best at D.H. as he’s proven to be injury-prone in the field and on the basepaths. Cease is having the best year of his career this year. His 2.68 ERA ranks 13th in the majors, and his 105 strikeouts rank 5th. Quintana was average for the Cubs, inconsistent, and with a higher ERA than during his White Sox career. As much as the Sosa trade was a landslide win for the Cubs, the Cease/Jimenez trade might be even more extensive — and is still paying dividends for the White Sox.

The Craig Kimbrell Trade Backfires For The White Sox

Last year, after an early playoff exit to the Athletics in 2020, the White Sox wanted to add more punch and swagger to their top-10 bullpen. The Cubs had lost 11-straight — and after trading Yu Darvish before the season – decided to tear down the team. They sent closer Craig Kimbrel, 8th all-time in saves, to the White Sox for 2nd baseman Nick Madrigal and relief pitcher Codi Heuer. On paper, it made perfect sense. Adding another dominant, late-inning reliever would help come playoff time. But Kimbrel never found his groove with the White Sox, posting a 5.09 ERA. He was traded before the 2022 season, and it ultimately cost them the #4 pick in the 2018 draft in Madrigal. If he stays healthy, this trade could eventually look bad for the Southsiders.

Building The Next Cubs/White Sox Blockbuster

Back to 2022. The Cubs are 18 games below .500 and will be sellers at the deadline. The White Sox are scuffling. Manager Tony LaRussa looks like he might have lost the clubhouse. Without an injection, the team could entirely fall apart. Luckily the Cubs have the pieces for them.

Cubs Send Catcher Willson Contreras and Starting Pitcher Kyle Hendricks to the White Sox

Contreras is the hottest player that will likely be moved during this year’s trade deadline. Contreras leads all catchers in home runs, slugging percentage, and OPS (on-base plus slugging.) He can split time behind the plate with Yasmani Grandal — keeping both fresh down the stretch. Acquiring a player like Contreras makes an already potent White Sox lineup even tougher.

Adding Kyle Hendricks gives the White Sox another veteran arm with playoff experience. He put together a gem on Friday against the Cardinals, allowing no runs on six hits while striking out six in 7.1 innings. Like Quintana, Hendricks is under contract next season with a $16M team option in 2024. Cease and flame thrower Michael Kopech can likely learn a lot from a guy like Kyle Hendricks.

White Sox Send Gavin Sheets, Jake Burger, Aaron Bummer, and Lenyn Sosa to the Cubs

Pulling off a trade like this will require major league talent. For the White Sox, they accomplish their goal of keeping Andrew Vaughn. For the Cubs, getting Sheets and Burger gives them two young bats with power to plug and play in the infield, and at D.H., Patrick Wisdom likely isn’t the long-term solution for the Cubs at 3rd — giving Burger an opportunity at the hot corner. He’s showing signs of putting it together at the significant league level with eight home runs this year and some clutch hitting – he’s worth the flier. Sheets needs at-bats that he isn’t likely to get with this White Sox team. Bummer’s ERA is down to 3.06 — but he’s had a couple of rough outings, and you have to wonder if he can be trusted in the clutch. He becomes a flip candidate for the Cubs or a reclamation project like Codi Hueur.  Lenyn Sosa just got called up to the White Sox after Danny Mendick’s season-ending injury. Sosa batted .331 with 14 home runs and 48 RBI in 62 games at Double-A Birmingham, giving the Cubs another option in the infield.