3 biggest Chicago Cubs offseason mistakes and how they can still be fixed

3 biggest Chicago Cubs offseason mistakes: Lack of a superstar signing

The Cubs openly avoided swimming in the deep end of Major League Baseball free agency this offseason. The Cubs did have preliminary conversations with the top free agents in shortstop Carlos Correa, Trea Turner, and Xander Bogaerts but the team did not appear willing to set the market at any position. Dansby Swanson was certainly a signing that elevated the Cubs at the Major League level but he is not the same caliber of superstar that the team has not had since the likes of Kris Bryant, Javier Baez, and Anthony Rizzo were traded in 2021.

Solution: The Winter of Shohei Ohtani and Manny Machado

Los Angeles Angels superstar two-way player Shohei Ohtani and San Diego Padres third baseman Manny Machado are set to potentially headline Major League Baseball's free-agent class next winter. Ohtani is a true free agent while Machado could opt out of the 10-year, $300MM contract that he signed with the Padres in 2019. Neither scenario is likely for the Cubs considering Machado still likely winds back up with the Padres and all of Major League Baseball will be interested in Ohani. Still, the Cubs will need to show a willingness, at the bare minimum, to meet their asking prices.