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.