The Crosstown Trade That Could Shake Up Chicago Baseball

With the Winter Meetings on the horizon, trade talks are likely to heat up. These talks will include Garrett Crochet, as his name has been floated in trade rumors all offseason. However, those rumors just picked up more steam, as Jon Morosi specifically noted two teams that could trade for Crochet.

. @MLB trade market update:

The Cubs and Reds are among the viable candidates to acquire White Sox ace Garrett Crochet.

Of note, the Cubs and White Sox have made 4 trades since 2017, beginning with the José Quintana deal. @MLBNetwork

— Jon Morosi (@jonmorosi) December 4, 2024

One of the teams Morosi mentions is the White Sox crosstown rival, the Chicago Cubs. This makes a lot of sense for both parties, as the Cubs would benefit from having Garrett Crochet in their rotation, while the White Sox could use some of their position player prospects.

There is precedent for a trade, as Morosi points out that there have been four trades between the White Sox and Cubs since 2017, when they swapped Jose Quintana for Dylan Cease and Eloy Jimenez, among others. The most notable trade since then is the Craig Kimbrel for Nick Madrigal trade, and we all know how that played out for both teams.

However, in this case, the two teams line up perfectly to get a blockbuster deal done. Let's see what a potential deal could look like:

As of right now, the Cubs have eight top-100 prospects on MLB Pipeline's list, with seven of them being position players. This is perfect for the White Sox, as they are in desperate need for top position player prospects.

The White Sox are likely to get at least one top-100 prospect, maybe two, depending on how high profile the headliner in the deal is.

Owen Cassie could be the perfect headliner, as there has been talk that the Cubs are willing to move him in the right deal. He would instantly become the best position player prospect in the White Sox system, as he is ranked at 34 on MLB Pipeline's top-100 list, but is likely to be listed higher in 2025 due to his impressive season in AAA.

In 127 games with Iowa, Cassie slashed .278/.375/.472 with 19 homeruns, 75 RBIs, and had 11 stolen bases. These would be some of the best numbers in the White Sox farm system and he likely would be ready to play in Chicago at some point in 2025. Cassie would be a great headliner, but the next pieces in the deal could vary depending on if there is a bidding war for Crochet's services.

Since he is a consensus top-40 prospect in baseball, the White Sox may not be able to get another top-100 prospect, as it is unclear on what exactly Crochet's value is.

However, if there is a bidding war, the Cubs could potentially add Jefferson Rojas in the deal, as he is currently ranked at 100 on the MLB Pipeline list. Rojas has a ton of potential and is only 19, so they may not be inclined to throw him in the deal.

If the Cubs offered Cassie and Rojas, that likely gets the deal done, as that would be a fantastic haul for the White Sox.

If the Cubs aren't inclined to give up Cassie, the White Sox could look for a deal revolving around James Triantos and Kevin Alcantara or Cam Smith, as all players are listed in the top 75 of the MLB Pipeline top-100 list. There are endless combinations of position player prospects they could swap for Crochet, so Chris Getz should be having extensive conversations with the Cubs.

If Chris Getz can create a bidding war for Crochet, the White Sox could leave this trade with a much bigger haul than people think, as Crochet has two years of cheap club control left, and will continue to improve as a MLB starter.