2. Nick Madrigal
This one is a bit of a copout, but Cubs fans will likely be able to end their disdain for Nick Madrigal this offseason.
Madrigal will finish the 2024 season on the IL and that has been the story of his time with the Cubs. When the Cubs acquired Madrigal in the 2021 Trade Deadline deal with the White Sox, the Cubs had visions of the former top Sox prospect being the focal point of the team's middle infield with Nico Hoerner. Instead, Madrigal's hit profile has been inconsistent when he's been healthy but his lack of availability is one of the biggest reasons he hasn't found success on the North Side.
With Isaac Paredes now firmly in place as the team's starting third baseman, Madrigal's future in Major League Baseball won't be with the Cubs.