5 free agents this Chicago Cubs must target this winter

Waiting for the first dominoes to fall in MLB free agency, we can only speculate about how aggressive the Chicago Cubs will get this winter. They won't just sign players that don't necessarily fit, as the names they have been connected to, via trade especially, are ones that only make sense on the current roster. Therefore, we've created a list of five players that make sense for the Cubs that they must target this winter. Diving right in, and addressing the unicorn in the room:

5 free agents the Cubs must target - 1. Shohei Ohtani

Shohei Ohtani is perhaps the greatest baseball player ever to step on a baseball field. It's just a fact of life at this point. I have concerns about the Chicago Cubs breaking the bank for him, but in the end, the caliber of player that Ohtani is is just light years ahead of the next guy right now. The talent is so overwhelming that if you get the chance, you must sign him on the principle that he's the greatest ever to play the game and is in his prime. With that, I have some concerns to consider.

I almost leaned for the Cubs to avoid signing Ohtani, and this is because of the simple nature of injuries. For one, Ohtani's Tommy John surgery doesn't guarantee he'll still be an elite pitcher when he does retake the mound in 2025. Of course, production is never guaranteed from anybody, but an injury to Ohtani that keeps him off the mound and out of the lineup hurts you more than one far cheaper player. Example: Cubs sign Ohtani, he misses two months with a hammy. Stretches you everywhere imaginable. Or, the Cubs sign Yamamoto and trade for Alonso. Yamamoto pulls a hammy, but at least the team still gets 40+ HRs from Alonso for around the same price in 2024—just a different perspective.

In the end, Ohtani is such an anomaly that you must roll the dice. The Cubs could get Ohtani and keep going from there. Nobody said they were going to avoid the luxury tax this season. If they blow past the luxury tax, every concern you can conjure up is null and void because they could get him and still have the high-end talent as depth after that.