3 ways the Chicago Cubs could screw up the MLB trade deadline

Realistically, 2023 is looking like a year where the Chicago Cubs will have to deal with not making the playoffs for the third straight year. Unless they go on a seriously convincing run over the next couple of months, the team is poised to re-group to try again next year. While that may be tough to swallow especially from a fan perspective, it's the way this game goes sometimes. That being said, there are some great opportunities this trade deadline that can put the team in a great position to win in 2024 and beyond.

That is assuming general manager Jed Hoyer and his front office don't colossally fail. Here are a few ways they could botch the 2023 trade deadline and how they can avoid making this season completely pointless.

1. Not trading Marcus Stroman

Marcus Stroman is most definitely going to opt out of his player option for 2024 and seek a larger contract for the future. Given the stellar performance he has put up this year, the man will probably get paid a solid chunk of change in the offseason. Whether the Cubs are the ones to give Stroman that money is something we'll have to wait and see. I would guess the answer to that is no given the amount of starting pitching depth that's already in the system. That depth is also a solid reason to trade him this week.

Hayden Wesneski is currently getting stretched out at Triple-A Iowa and he will likely be taking Stroman's spot in the starting rotation. Although he struggled earlier this year, he is on a hot streak in Iowa right now and he still has one of the best sliders in the game. Caleb Kilian, Javier Assad, and Ben Brown are also options not to mention there is a wealth of other free-agent starting pitching that will be available over the winter. All of these reasons point to the Cubs moving Stroman this trade deadline to get some assets for him while he is dealing.

Postseason contenders always need starting pitching meaning the Cubs could cash in on a bidding war for the 32-year-old righty. Stroman currently owns a 3.09 ERA (third best in the National League) while he is tied for the league lead in quality starts with 15. The Texas Rangers, Atlanta Braves, and Los Angeles Dodgers are all in need of another solid starter and they each have prospects to move. The Cubs would be wise to make this move when you consider all the starting pitching options they have for 2024.