4 White Sox players who could be Cubs trade targets this winter

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Just as the Cubs' dynasty we all hoped for never came to be after the team won it all in 2016, in recent years, the White Sox have failed in an even more dramatic way, completely failing to become the contender everyone expected coming out of its rebuild toward the end of the last decade.

After advancing to the Wild Card round in 2020 and winning the AL Central, only to fall in the ALDS in 2021, the wheels have totally fallen off on the South Side. The White Sox were a .500 team in 2022 and burst into flames this year, going 61-101 - prompting the club to clean house and install a new front office regime. Now, that regime is ready to clean house and is willing to listen on 'any' player on the roster.

Meanwhile, the Cubs have re-tooled in the last three years, quickly setting themselves to return to the national stage in 2024. With several needs on the roster and a crosstown team in need of a fresh start, might we see these two teams hook up on a big-time trade this winter? Time will tell - but there are 4 guys worth mentioning as the hot stove heats up.

4 White Sox players who could be Cubs trade targets this winter - #4: Bringing Dylan Cease back could fortify the top of the rotation

When the Cubs traded Eloy Jimenez (more on him in a minute) and Dylan Cease to the White Sox in 2017 in exchange for Jose Quintana, the former was a far more highly-regarded prospect. But injuries have kept Jimenez from realizing his full potential, while Cease has shown he's capable of being one of the best starting pitchers in the league.

The Cubs have a pipeline of young arms poised to crack the big league roster in the next couple seasons, but adding another top-of-the-rotation piece alongside Justin Steele would set up a potential postseason staff nicely. Cease is coming off a bit of a down year and the odds the Sox trade him are '90 percent', according to reports - so the match isn't hard to make.

In 2023, the right-hander worked to a 4.58 ERA in 33 starts - more than a two run jump over his 2022 AL Cy Young runner-up campaign. But FIP suggests he was mildly unlucky (3.72) - which is hardly a surprise given the defense behind him. Cease still has two years of team control left, making him of the Chicago's most valuable trade chips. He wouldn't come cheap, but could help the Cubs shore up the rotation in a big way heading into 2024.

4 White Sox players who could be Cubs trade targets this winter - #3: Eloy Jimenez could fill the DH spot, add power to the lineup

Somehow, Eloy Jimenez is just now approaching his 27th birthday - but he's already four years removed from his 2019 fourth-place finish in AL Rookie of the Year balloting. He's never come close to replicating that 31-homer campaign, with the exception of the 60-game 2020 season - and seeing him moved wouldn't surprise anyone at this point.

The Cubs have a dire need of power in the middle of the order and, unlike the White Sox, wouldn't need to endure Jimenez' brutal defense in the outfield in order to get his bat in the lineup. He could slot in as the team's full-time DH which would, hopefully, help keep him healthy - something that's been a major struggle to this point in his career.

The six-year, $43 million extension he signed with the Sox runs through 2024 - and contains a pair of team options for 2025 and 2026 - so if things went sideways, the Cubs would have no long-term risk here, while also being able to take advantage of any potential best-case scenario via those options. It would be very odd to see Chicago re-acquire its former top prospect, but with a weak free agent class of bats, Jed Hoyer might have to get creative.

4 White Sox players who could be Cubs trade targets this winter - #2: Yoan Moncada could be a (pricey) answer at third base

The centerpiece that came back in the Chris Sale trade with Boston, Yoan Moncada has never lived up to the hype that once surrounded him - or the heavily back-loaded five-year contract the White Sox gave him that runs through 2024.

Due $17.8 million next season and coming off a disappointing 1.2 fWAR season, finding a match in a Moncada trade could prove a challenge for new White Sox GM Chris Getz. He's either going to have to throw in some cash to get something of value in return, or settle for a deal centered around low-level, high-risk pieces in order to move payroll.

The Cubs have a massive hole to fill at third base and, much the same as Jimenez poses no long-term threat to the organization's stability, Moncada's 2025 option can be bought out for just $5 million. Moncada hasn't been an All-Star-caliber threat in four years and the Sox would be selling low. But barring a dramatic turnaround, Chicago will cut him loose at the end of 2024 to avoid paying him a $25 million salary in 2025, so getting what they can, while they can, might prove beneficial.

4 White Sox players who could be Cubs trade targets this winter - #1: Luis Robert would be a lineup-altering answer in center field

Hands-down the White Sox' most valuable asset, center fielder Luis Robert is coming off a big year on the South Side - winning his first Silver Slugger and earning his first All-Star selection in 2023. The outfielder turned in a 5.0 fWAR campaign and is just 26 years old, under team control through 2027 via team options.

The cost to acquire Robert would be astronomical - and I have a hard time believing Hoyer would pony up what it would take to bring him to the North Side, especially with top prospect Pete Crow-Armstrong knocking on the door, poised to roam center field at Wrigley for years to come.

But the Cubs need run producers and Robert has shown that, even with little to no supporting cast, he's capable of being just that. Hoyer has the prospect capital he'd need to pull off such a blockbuster, but this is easily the longest shot of the bunch because of all the reasons I just outlined.

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