Trade Proposal Would Send White Sox Ace to Cubs Before Opening Day

Earlier in the offseason, the Chicago White Sox trading Dylan Cease before Opening Day seemed destined to happen. Now, the ace’s market has cooled off considerably, but perhaps a deal with the team’s crosstown rival, the Chicago Cubs, should be on the table.

While there’s no indication that a trade is in the works, it would make sense for both teams for Cease to move to the North Side. The White Sox are looking to trade Cease as they continue their rebuild, and the Cubs, whom MLB.com ranks as having the second-best farm system in the majors, desperately need to bolster their starting rotation if they want to be competitive in 2024.

With that in mind, a trade between the Cubs and White Sox could look as follows:

• Cubs receive: Dylan Cease (RHP)
• White Sox receive: Jordan Wicks (LHP), Hayden Wesneski (RHP), David Bote (INF)

In 2023, Cease went 7-9 with a 4.58 ERA, 1.42 WHIP, and 214 strikeouts, which was a noticeable decline from his career-year stats in 2022, though the White Sox’s league-worst defense certainly didn’t help. Despite being snubbed by All-Star selection, Cease’s 2022 ERA of 2.20 was the third-best in the majors, and his AL Pitcher of the Month wins in both June and July made him the first pitcher in White Sox history to win in consecutive months.

Earlier in the winter, Cease’s trade market was extremely hot. The New York Yankees, Baltimore Orioles, Seattle Mariners and a slew of other teams were linked to the 28-year-old, but a trade never came to be. On January 7, USA Today’s Bob Nightengale reported the White Sox were looking for “a package of at least two top-100 prospects and two other players” for Cease, an asking price that NY Post’s Jon Heyman quoted an MLB general manager referring to as “the sun and the moon.”

Still, a February 22 survey conducted by The Athletic’s Jayson Stark found that of the 31 MLB executives, former executives, coaches and scouts queried, 14 chose Cease as most likely to be in a different uniform by Opening Day.

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Acquiring Dylan Cease Would Bolster the Cubs’ Otherwise Shaky Starting Rotation

Looking at the Cubs’ projected starting rotation for 2024, it’s clear they lack a strong No. 2 to put behind Justin Steele.

Chicago lost Marcus Stroman to free agency at the end of 2023, and while newly-acquired Japanese pitcher Shōta Imanaga was a very solid addition, the rotation still leaves Steele as the only certifiable ace.

On February 24, manager Craig Counsell told The Athletic’s Patrick Mooney that he plans to use a sixth starter this season, at least while Imanaga adjusts to pitching every five days. With that in mind, the team’s rotation will likely fall as follows:

• Justin Steele (LHP)
• Shōta Imanaga (LHP)
• Kyle Hendricks (RHP)
• Jameson Taillon (RHP)
• Javier Assad (RHP)
• Jordan Wicks (LHP)

Aside from his needing time to transition to the five-day pitching cycle, Imanaga is a left-hander like Steele, which leans to him fitting far better as a No. 3 starter than No. 2, even if his spring training starts have been very encouraging. Veteran Kyle Hendricks came back well after his shoulder surgery in 2022, but he’s simply no longer the top-of-the-rotation pitcher he was earlier in his career, so it’s almost certain he’ll start under Imanaga.

Without a strong second starter after Steele, the Cubs’ starting rotation feels quite incomplete, as though everyone in the rotation has been shifted up to fill a gap. The Cubs know this, too.

Since missing out on both two-way superstar Shohei Ohtani and Japanese pitcher Yoshinobu Yamamoto earlier in the winter, Chicago has been repeatedly linked to free-agent starters Blake Snell and Jordan Montgomery, both of whom are still available.

Snell and Montgomery were both standing firm in their demands for long-term deals out of free agency, but as the offseason wore on and their options thinned, they’ve both had to readjust their asking prices.

Montgomery entered free agency looking for a bigger contract that Aaron Nola’s seven-year, $172 million deal with the Philadelphia Phillies. Now, Bleacher Report’s Zachary D. Rymer predicts he’ll end up on a three-year, $75 million contract with opt-outs after 2024 and 2025. This definitely makes an eleventh-hour deal with the Cubs more likely, but it’s still an awful lot of money for a pitcher who may leave the organization after one season to get a better contract.

In January, the White Sox avoided arbitration with Cease, agreeing to a one-year, $8 million deal for 2024. Cease enters this season with two more years of club control before he hits free agency after 2025, making a trade all the more attractive for the Cubs, who are looking to take advantage of their immediate contention window.

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Could This Cubs-White Sox Deal Happen?

If this trade was proposed, which team would turn it down?

The Cubs would give up Jordan Wicks, Hayden Wesneski, and David Bote, with Wicks, who is currently ranked as the organization’s No. 9 prospect, definitely being the biggest loss. The 6-foot-3 left-hander is one of the Cubs’ most promising young pitchers, with Fangraphs’ David Laurila describing his changeup as “not only the best in the system, [but] it could prove to be one of the best in the National League.”

Meanwhile, it seems as though the Cubs are getting close to giving up on Wesneski, who the team acquired from the Yankees in 2022. Once a highly-regarded prospect, Wesneski won the Cubs’ fifth starting rotation slot last season, but some underwhelming starts saw him optioned to Triple-A in May. The 26-year-old bounced between the majors and Triple-A for the rest of 2023, finishing the season with a 4.63 ERA in 89.1 innings.

Infielder David Bote has appeared in just 41 major-league games since the start of 2022 and played all of 2023 in the minors, despite hitting .329/.438/.589 in 20 games in June. It’s unclear if there’s an organizational reason why the Cubs seem set on keeping the 30-year-old in Triple-A, but it’s clear that he’s not going to get a real shot in the majors with the team.

On the other side of the trade, the White Sox still need pitching and infield depth. Second base has been a revolving door for the South Siders for years, and Bote could finally get the major-league opportunity he’s been waiting for.

The White Sox made a range of moves to bolster their farm system this winter, but pitching is still an area they need to add to, and Wicks and Wesneski would both be huge assets, especially if Wesneski can return to the dominant form he displayed in 2022.

According to Nightengale, the White Sox want a package of “at least two top-100 prospects and two other players” for Cease, which means they may want a fourth player added to the package. Second baseman James Triantos, who’s currently ranked as the Cubs’ No. 7 prospect, could be considered, but adding another player they deem to be a future game-changer could be the dealbreaker.

While there’s no indication that the Cubs are interested in acquiring Cease at the moment, it may be a consideration later in the year. The Cubs need to add a top starter to their rotation if they want to play deep into October, and if it doesn’t happen before Opening Day, they will almost certainly have to trade for one at the midseason deadline.

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