An ideal starting rotation for the Chicago Cubs in 2024

Mulling over the list of free agent options and determining what would be an ideal starting rotation for the Chicago Cubs in 2024.
World Series - Arizona Diamondbacks v Texas Rangers - Game Two
World Series - Arizona Diamondbacks v Texas Rangers - Game Two / Sam Hodde/GettyImages
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After a disappointing finish to the 2023 season which saw the Chicago Cubs narrowly miss the postseason by one game, questions can begin to arise as to what exactly could have been done better in order to avoid the spiral that took place at the end of the year. One of those questions is simply how much blame can be put on the starting rotation.

Although you can place the blame on more than any one person, or areas, for that matter, the fact remains that if the Cubs’ front office finds a way to strengthen the starting pitching, the team will have a much better chance at competing. Based on pending free agents this winter, let’s glance at an ideal starting rotation for 2024:

  • Jordan Montgomery
  • Justin Steele
  • Sonny Gray
  • Kyle Hendricks
  • Jameson Taillon/Jordan Wicks/Javier Assad

Acquiring two key free agents in Montgomery and Gray gives the team a rotation that is packed with upper-echelon-type starters who can reach ace potential when truly on their game. Justin Steele and Kyle Hendricks are a given, and to be fair, Jameson Taillon most likely is too. However, I’d be keen to give Jordan Wicks or Javier Assad their fair chance in 2024.

It’s no secret Taillon struggled for much of the 2023 campaign. Just because the Cubs inked him to a four-year, 64.0M deal last winter doesn’t mean they are forced to keep him in the rotation. His leash needs to be shorter next season. Ideally, he pitches with more consistency, and Wicks and Assad are both used as depth pieces in a bulk-relief/start-when-necessary role.

Still, it’s hard to not automatically pencil someone like Javier Assad into the rotation already. In his second year at the major league level, Assad recorded a 3.05 ERA in 109.1 IP. 53.2 of those innings were in a starting role, where his 3.02 ERA proved that he has what it takes to be in an MLB rotation. Taillon, on the other hand, recorded a 4.84 ERA, which was well below his career average of 4.00 and the MLB average of 4.33.

If the Cubs are to acquire two starters via free agency, or trade, it will essentially lock up the first four spots in the rotation, and we’ll hopefully see a battle for the 5th spot between the final three, with the front office deeming whoever deserves it most worthy of the nod. With the Cubs eyeing a postseason berth next year, it’s safe to assume this winter will be jam-packed with Cubs rumors, signings, and trades.

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