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Refreshed Offseason Outlook Part II: Potential White Sox Trades for Darvish, Gray, and Lynn

With trade rumors swirling, we take a look at what it would take for the White Sox to acquire Yu Darvish, Sonny Gray, or Lance Lynn.
Yu Darvish

Photo: John Antonoff/Chicago Sun-Times

In the first installment of Refreshed Offseason Outlook, we began to look at the White Sox offseason possibilities, beginning with the most pressing need: starting pitching. After starting with free agency (not much after Trevor Bauer), we turned our attention to the trade market, where I broke down what Blake Snell would bring to the White Sox and what a potential trade package would look like.

With Winter Meetings happening this week, let’s take a closer look at some of the other trade targets the White Sox could pursue. Specifically, those available that fit the White Sox needs include Yu Darvish, Sonny Gray, and Lance Lynn (Zack Wheeler has also been mentioned but emphatically shot down by the Phillies owner). For ease of reference, I have created the chart below to compare and contrast each player’s age, remaining salary, and stats from the 2020 season.



Contract Status





Yu Darvish


3 yrs/$59 mil





Sonny Gray


2 yrs/$20.4 mil





Lance Lynn


1 yr/$9.3 mil





Yu Darvish

Yu Darvish

Photo: Kamil Krzaczynski

Darvish would be my preferred option, so we will start there. Darvish has enjoyed a fantastic career since coming over from Japan and has cemented himself time and again as one of the true aces in baseball. He has experienced his share of hiccups, specifically missing the 2015 season with Tommy John surgery, poor World Series performance (likely due to the Astros cheating scandal), and a rough start to his Cubs career in 2018 that tricked over into the first part of 2019.

However, after each of these hiccups, Darvish has brought himself back to elite status, and when healthy has been a true workhorse. Over his eight seasons, he has finished top 20 in innings pitched four times with a career 3.47 ERA and an 11.12 K/9. He also appears to be getting even better, as evidenced by his BB/9 that could be an Achilles heel for him in the past but has come down each of the last three seasons. Lining him up at the top of a rotation with Lucas Giolito and Dallas Keuchel would be a lethal 1-2-3 combination.

Originally appearing to be a disaster of a free-agent contract, Darvish’s remaining three years and $59 million is certainly within the going rate for a pitcher of his caliber and provides any team acquiring him with cost control. But with the Cubs determined to shed payroll and retool their team, they may very well look to deal the 2020 Cy Young runner-up for an influx of young talent that the White Sox have plenty of. However, after the Jose Quintana fleecing, dealing with the crosstown rival may prove to be too tall of a task.

For a comparable trade in recent history, we can look to both the Astros acquisitions of aces Justin Verlander and Zach Greinke, who were 34 and 35 years old, respectively, at the times they were dealt. Verlander had an almost identical two and a half years and $56 million left on his contract when he was traded, and Greinke had the same two and a half years with almost $70 million left. The only difference between Darvish and these two is that Darvish might actually be better than the two of them when they were dealt; this is certainly true for Verlander at the end of his Tigers career.

The package for Verlander included the Astros' third, ninth, and 11th ranked prospects and Greinke cost the third, fourth, fifth, and 22nd ranked prospects within the organization, according to MLB Pipeline. For reference, the White Sox top prospects consist of the following:




Andrew Vaughn


Michael Kopech


Nick Madrigal


Garrett Crochet


Dane Dunning


Jared Kelley


Jonathan Stiever


Matthew Thompson


Micker Adolfo


Gavin Sheets


Andrew Dalquist

The White Sox organization is stronger than the Astros at the time of these trades and the key separator is that the White Sox top prospects are already major-league level contributors. But for a Cubs team looking to retool with Major League-ready talent or close to it, there may be a match there.

The Cubs would likely be looking for pitching in return for their ace, so a package headlined by Michael Kopech would seem the most probable. Using the Verlander and Greinke packages as barometers, the package beyond Kopech would have to include two to three of the Sox prospects ranked 6-11. The package should exclude Madrigal, Crochet, and Dunning given how highly they are thought of around the league, allowing Sox fans to breathe a sigh of relief.

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The other interesting name to consider here is Dylan Cease. Still just 24 years old and supremely talented, the Cubs are intimately familiar with their former prized prospect and could be interested in bringing his services back to the North Side. Perhaps a package of Kopech, Cease, and a prospect ranked eighth or slightly below could be enough to pry Darvish away from the Cubs.

Sonny Gray

Sonny Gray Trade

Photo: Daniel Shirey/Getty Images

Gray is the youngest of the trade options but also comes with the most performance risk. He was a dominant pitcher his first three seasons with the A’s before disappointing seasons in 2016 with Oakland and 2018 with the Yankees. Prior to the 2019 season, Gray signed a free-agent deal with the Reds and seemed to revive his career once again.

Finishing seventh in NL Cy Young voting in 2019, Gray had a microscopic ERA of 2.87 over 175.1 innings. In 2020, he missed some time with injury but still was effective when called upon. In Gray’s Cincinnati career, he has ticked up his K/9 to over 9.50 for the first two times in his career, but with the increased strikeouts have also come increased walks that have been the bane of his pitching existence. Gray’s lack of control reared its head throughout the 2020 campaign to the tune of over four walks per nine innings.

But Gray also does come with cost certainty, and he actually has a $12 million club option for a third season. With the Reds also reportedly facing budget concerns, they are working hard to get out of Gray’s contract. While the Reds are not the Rays in terms of trades, it is fair to wonder why exactly they are making Gray available given that he is relatively cheap for the performance he has provided, as they do have more expensive contracts on their books.

Regardless, Gray would be an immediate upgrade for the White Sox third rotation spot and the cost would be less than Darvish. It is difficult to come up with a comparable trade for Gray at this point in his career. He was traded from the A’s to the Yankees in 2017 but those were different circumstances in terms of age, performance, and contract status.

One would have to believe that Gray would cost less than Darvish, so the Sox should be able to hold onto both Vaughn and Kopech in this scenario. A package headlined by Dunning and including a second name from the list above would likely be enough to get the deal done. If the Reds are looking for quantity, a package headlined by Stiever and including two more young arms would be fair compensation for Gray’s services.

Lance Lynn

Lance Lynn Trade

Photo: Jerome Miron/USA-TODAY Sports

Lynn is the most short-term option available, and Sox fans will recall the team inquiring about his services at the 2020 trade deadline. But with only one year left on his contract as Lynn will be 34 years of age on Opening Day 2021, he should also be the cheapest.

Lynn has been steady and fairly consistent throughout his career but lacks the dominance of the aforementioned options. He has a career K/9 under 9.0 but has successfully avoided giving out free passes for the most part. The lack of strikeouts leads to less than ideal peripheral statistics, but Lynn has regularly outperformed these expectations throughout his career. And with the Rangers entering a rebuilding phase, there is no reason to keep the veteran on their roster.

With this in mind, just pairing Stiever with one of the prospects ranked below him should be more than enough to secure Lynn’s services for the 2021 season. Going this route still allows the White Sox the flexibility to spend money in free agency elsewhere. It would also allow the younger arms more opportunities to prove what they are capable of at the big league level.

This move would not be as splashy as Gray, or certainly Darvish, but it would provide the White Sox with some stability behind Giolito and Keuchel.

Whichever direction the Sox choose, the team is clearly at a point where it is time to start cashing in the prospect capital for established pieces at the Major League level. Understanding this, fans have to be aware that giving up prospects can always look silly with two to three years of hindsight.

So if and when one or more of the prospects they trade away turns into a key contributor for a good team, we as White Sox fans will have to live with that, knowing that this is the sacrifice the team is making to win now.