Cubs-Sox Trades That Make Sense-But Won’t Happen

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There have been several Cubs-Sox trades over the years; some have worked out, some have not. The most recent trade was one that would definitely count as a one-sided trade. In 2017, the Cubs were coming off their first World Series championship in 108 years. With eyes on a repeat title, they turned to the South Siders for some pitching help. The Cubs sent young prospects Eloy Jimenez and Dylan Cease to the White Sox in exchange for left-handed starter Jose Quintana.

The trade made sense at the time, as the Cubs needed to solidify their rotation, and Quintana had been a solid #2 starter for the Sox. The Sox were in the middle of a rebuild and were looking to add young prospects. From the standpoint of need, it was a perfect trade. However, the deal went south for the Cubs when Quintana failed to meet expectations. Four years later, Jimenez and Cease may be contributing to a deep Sox playoff run. So what looked good on paper turned out to be an epic fail for the North Siders.

Cubs-Sox Trades: Let’s Make A Deal 2021 Style

Fast forward four years to 2021. The Cubs find themselves caught in the uncomfortable position between contention and rebuilding. They find themselves mired in fourth place in the National League Central, with no legitimate path to meaningful postseason play. They also have several key players in the last year of their contracts. The White Sox, on the other hand, have come through their rebuild, and have a commanding lead in the American League Central. They are possibly looking to shore up areas of need as they approach the postseason. Could there be a fit between the two teams that are battling for the heart and soul of the Windy City?

Generally, midseason trades in baseball occur because contending teams are looking to upgrade at certain positions. Non-contenders are hoping to unload salaries while acquiring good prospects. Once teams decide whether they are buyers or sellers, the trading can begin. In the case of Chicago, the Sox are clearly buyers while the Cubs are reluctant sellers. That said, it could be fun to explore possible trades between the two teams.

White Sox Needs

The Sox have played well to this point, despite several key injuries. While they are hoping that Eloy Jimenez, Luis Robert, and Yasmani Grandal can contribute after their returns from injuries, they still have clear needs. While fans may disagree on the severity of these needs, there are three areas many fans have identified for their favorite team. At this point, it would appear that the White Sox could use upgrades in these spots: a bat, the bullpen, and second base. Solidifying these areas could give the Sox the edge they need going into October.

Professional Hitter

No matter how one analyzes it, the Sox could use an experienced hitter to help solidify their lineup. As currently made up, they could most readily use that upgrade at right field or second base. While the return of those named above should help the offense, they still don’t have a right field candidate or second baseman who strikes fear into the hearts of opposing pitchers. So it would be nice to add a veteran hitter for the stretch run.

Second Baseman

Nick Madrigal was well on his way to a solid season at second base before suffering a season-ending injury last month. While his future is bright, he will not be a factor in 2021. The two players currently sharing second base, Leury Garcia and Danny Mendick, have done a decent job holding down the fort. However, expecting either to step up and be solid offensively is not an ideal situation. Garcia has had his moments, but, he has never hit consistently. Besides that, he is a super-utility player, and committing him to one position eliminates a valuable weapon. The Sox could use an upgrade here.

The Bullpen

The bullpen is an area where Sox fans can all agree. Based on performance to this point, counting on the bullpen to be there when they need it is playing with fire. Ironically, the bullpen was looked at as the biggest strength of the team in spring training. With several returnees and the addition of Michael Kopech, many expected that the pen would be among the AL’s elite. However, the bullpen, with the exception of Kopech and closer Liam Hendriks, has been a major disappointment. Nobody expects the White Sox to stand pat at the deadline; it seems certain that the South Siders will trade for some bullpen help. The only questions are who and when.

Enter The Cubs

So, how do the Cubs fit into the puzzle here? What players do they have who could help lift the White Sox in a run to October? Ideally, the Cubs would be looking to deal some veteran players who are on expiring contracts. They have a veritable plethora from which to choose. Yet, there are a select three with expiring contracts, who just might help put the Sox over the top.

Outfield Bat

The first Cubs target for the White Sox could be Kris Bryant. The former Rookie of the Year (2015) and NL Most Valuable Player (2016) has had a very productive season so far. While his average is lower than teams may like, Bryant is slashing .264/.346/.489. He has an OPS+ of 127 and would be a significant upgrade over whomever the Sox play in right field. (Yes, Adam Engel currently has a higher OPS+ of 148. but over a much smaller sample size.) Additionally, Bryant can play five positions, giving the Sox more flexibility on defense. He would be an excellent addition to the Sox.

Second Base

This may not be as obvious as Bryant, but how about adding a Gold Glove-caliber defender with plus power? Javier Baez, the current Cubs shortstop, will also be a free agent after the 2021 season. While he has played shortstop for the last three seasons, he won a ring in 2016, teaming with shortstop Addison Russell. Yes, he strikes out a lot, but his power potential would be very alluring to a Sox team struggling to hit the long ball. He would fit in well at second base with Tim Anderson at shortstop. The Sox should consider the possibility

The Bullpen

Finally, this may be the area of biggest need for the South Siders. The regression from 2020 to 2021 has been stunning, and something must get done here if the Sox are to make the desired playoff run. Here, the Cubs’ closer Craig Kimbrel would be a perfect fit. He has had an outstanding season for the Cubs and would be an ideal setup man for Sox closer Liam Hendriks. The only question would be whether Kimbrel would accept the move from closer to setup man. We suspect that the chance to win a ring would be enough to assuage any hurt feelings.

The Return For The Cubs

Identifying players that would fill the needs of the White Sox is rather easy. One need not have a Ph.D. in baseballology to come up with such a list. The tricky part is just what, or how much. the Cubs could get in return for dealing their veterans to the South Side. This is where Jed Hoyer and Rick Hahn would have to be creative, as well as a little flexible. Both men have a lot at stake here: Hoyer is looking to quickly restock the cupboard for the Cubs, and avoid another painful total rebuild. Hahn is looking to upgrade the White Sox without giving away too many future pieces. Here is one way to move past any roadblocks and make potential deals.

What The Sox Should Be Willing To Give Up

Now we get to the fun part, the part that you have been waiting to see, and how we get there. Okay, the short version is that, in return for any of the Cubs players listed above, the Sox would make certain players available. Or, perhaps more accurate, the Sox would make some players unavailable. Remember, we are thinking outside the box here, so your indulgence would be greatly appreciated.

One more point before we get to “The List,” and hopefully, this will not complicate things. The proposed trades can be multi-layered, with many contingencies and moving parts. The goal here is to provide a framework for any trades. Both trading parties would need to be flexible and willing to negotiate. You know, think outside the box.

So, here is how any Cubs/Sox trade would happen. The White Sox would provide the Cubs with a list of protected players, i.e., players that would be off-limits to the Cubs. One variation of the list would look like this:

MLB Rostered Players

All starting pitchers, relievers Hendriks, Kopech, Garrett Crochet, Aaron Bummer, and Codi Heuer

All position players except Brian Goodwin, Billy Hamilton, Seby Zavala, Danny Mendick, and Jake Burger

Minor League Players

Yoelqui Cespedes

Colson Montgomery

Jarred Kelley

Matt Thompson

Andrew Dahlquist

Norge Vera

Konnor Pilkington

Elijah Tatis

The Nuts And Bolts Of The Deal

With that in mind, here is how any trade would work: The White Sox would identify the player they most desire to acquire. At that point, the Cubs could pick any three players who are not on the protected list. For example, the deal could end up being Kris Bryant for Jonathan Stiever, Micker Adolfo, and Jake Burger. That would be a good haul for the Cubs, as they would get the 4th, 6th, and 11th rated Sox prospects. Of course, the Sox may balk at that, and reconsider the protected list.

After the teams have a verbal agreement, the Sox would add three players to the protected list, and perhaps identify a second Cubs player. In exchange for this player, the Cubs would select two players from the unprotected list. At that point, the Sox would protect two more players, and choose the third player. The Cubs would then choose two more available players, and the deal could be finalized. The net result of all this wheeling-dealing would be that the Sox would be in a solid position for 2021, and the Cubs would add some excellent prospects. Seems like a win-win here.

Why No Trades Will Happen

Fans of both Windy City teams may question the sanity of the author here. Fair enough, there is a lot to think about here, and we may be well off the mark. However, trades are always fun to consider, no matter whether you root for the North Siders or the South Siders. Maybe the Sox would want to protect more players. Maybe the Cubs would demand a higher return. This is all conjecture, so nobody knows for sure. We doubt that neither Jed Hoyer nor Rick Hahn is paying attention to us, although both are definitely working the phones.

Not to worry about any of this happening, as there is no chance the two teams will make a deal. Fans of both teams know why any deal is unworkable. The Cubs remember how the tenure of Jose Quintana worked out on the North Side. They would most assuredly impose the dreaded “Cub Tax” on any crosstown trade. Conversely, the Sox are still somewhat haunted by the memories of the James Shields trade. Many fans still get triggered at any sighting of Fernando Tatis, Jr. doing something crazy for the Padres. Imagine a Tatis, Jr. lookalike on the North Side. That could be 100 times worth for Sox fans.

There is no doubt that both the Cubs and Sox will be making deals in the next eight days. However, don’t look for any players to move across town. Even though there may be a good fit, both general managers are highly unlikely to pull that trigger. It is fun to think about and debate for fans of both teams. Yet, at the end of the day, all of the speculations will be just that; and, maybe, that is how it should be. Ya gotta love Chicago baseball!

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Main image credit: Embed from Getty Images

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Mike Fisk is a lifelong baseball fan. For him, there is nothing like being at a baseball game, with the sights, the sounds, the smells. Writing about baseball is a bonus!