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

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There is no doubt that the Chicago Cubs have had a successful off-season. While there certainly are free agents that the Cubs missed out on this offseason, there is no question that the team was active. The signings that the Cubs have made this winter should raise expectations for the team when Opening Day arrives at the end of March and that is reason to be excited for the season ahead.

Despite the success that the Cubs have had this off-season, there were also mistakes that were made. That is why the Cubs are still a clear level below the St. Louis Cardinals in regard to competing in the National League Central division. Whether or not the Cubs are on the same plan as the Milwaukee Brewers is debated but if they show a willingness to correct the mistakes that were made, they could take a second step forward.

3 biggest Chicago Cubs offseason mistakes: No extensions for Ian Happ or Nico Hoerner

The Cubs entered the offseason with one of their goals being to make progress on potential contract extensions for left fielder Ian Happ and second baseman Nico Hoerner. Happ is a free agent after this season, and Hoerner is set to reach free agency in 2026.

Solution: Trade Happ and sign Hoerner to a contract extension in-season

Unless Happ signs an extension before Opening Day, it seems likely that he will test free agency after the season given there does not appear to be any progress made on a new deal with the Cubs. With that in mind, the solution for the Cubs to this mistake would be to trade Happ at the Major League Baseball trade deadline. If done right, the Cubs could be in a position to move Happ at the deadline to address another area of need at the Major League level. Mind you, this is predicated on one of the following--Pete Crow-Armstrong, Brennen Davis, Kevin Alcantara, or Owne Caissie--taking another step forward in their development toward the Major League level.

For Hoerner, the goal for the Cubs should still be to sign their starting second baseman to an extension. The situation with Hoerner is not nearly as dire considering he does not reach free agent until 2026.

Championship Series - San Diego Padres v Philadelphia Phillies - Game Five / Tim Nwachukwu/GettyImages

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.

Milwaukee Brewers v Chicago Cubs / Matt Dirksen/GettyImages

3 biggest Chicago Cubs offseason mistakes: Lack of an ace

A curiosity of the Chicago Cubs' offseason was how open they were in avoiding the starting pitchers at the top of the free-agent class. The Cubs showed little to no interest in the likes of Justin Verlander, Jacob deGrom, and Carlos Rodon. Veteran starting pitcher Jameson Taillon will provide stability to the Cubs' starting rotation but much like Marcus Stroman, he is a capable secondary starting pitcher but may not be considered an ace.

Next. 4 Cubs who don't deserve to be on 2023 40-man roster. dark

Solution: The emergence of Justin Steele and Hayden Wesneski

During the second half of the 2022 season, the Cubs had two starting pitchers that truly stood out. Those starting pitchers are Justin Steele and Hayden Wesneski. Steele posted a 0.98 ERA in 36.2 innings pitched during the second half of the season while Wesneski posted a 2.18 ERA in 6 appearances (4 starts). There is no question that Wesneski has the best arsenal of any pitcher within the Cubs' system. For Steele, if he can work on his secondary offerings to utilize with his fastball, then the success he saw in the second half should transfer over to 2023. The potential is there for one of Steele or Wesneski to emerge as the team's ace in 2023.

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