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.

5 free agents the Cubs must target - 2. Yoshinobu Yamamoto

Moving right into the second biggest fish in MLB free agency, Yoshinobu Yamamoto. At 25 years old, Yamamoto has spent seven years in Japan and has posted elite numbers. For his career, he owns a sparkly 1.72 ERA. More impressively, he does it while pitching with a solid workload year in and year out. He eclipsed 170 innings pitched for the third year this season while touching 193 in the previous two seasons.

Given how sought after Kodai Senga was last winter, Yamamoto's numbers in Japan blow Senga out of the water. Projection-wise, the Athletic listed Yamamoto for around seven years/210.M or about 30.0M per season. Yamamoto will quickly adapt and excel rapidly at the MLB level. This is the most brilliant move if the Cubs want to make a serious splash in the starting rotation without breaking the bank for Shohei Ohtani.

5 free agents the Cubs must target - 4. Justin Turner

Justin Turner on a one-year deal makes sense for the Cubs if they fail to sign or trade for an infielder this winter. Although primarily a DH now, Turner can still fill in nicely if need be, as he appeared in 58 games playing in the field between first base, second, and third in 2023 for Boston. Maybe not the greatest defensively, but his bat-to-ball skills are still elite, and he certainly adds cheap offensive production.

In 2023, Turner slashed .276/.345/.455 with 23 HRs and 96 RBIs. So much of the spotlight these days goes to the younger budding superstars, or the Shohei Ohtani's of the world, that stats like these often don't receive the credit they deserve anymore. The fact remains Turner can still mash. He is an acceptable backup target if the Cubs need somebody later in free agency. He certainly won't be a primary target, but his offensive prowess and non-bank-breaking contract demands for perhaps a bridge to Matt Shaw are hard to ignore.

5 free agents the Cubs must target - 5. Josh Hader

With obvious ties to Craig Counsell, this move makes sense for all parties involved. Hader is one of the most elite relievers in the game; the Cubs bullpen fell apart at the end of the season, the ties to Counsell, the need for a true closer (Although Alzolay was spectacular in his role), the lack of left-handed pitching in the bullpen in 2023, the time being now for the Cubs to go past the luxury tax threshold and go for it, it all just makes sense and fits perfectly if you're Jed Hoyer and the Chicago Cubs.

His track record speaks for itself: a career 2.50 ERA and at least 33 saves every year since 2019 (not including 2020 for COVID-19). A five-time all-star, Hader's elite 13.6 K/9, including 85 punch-outs in 56.1 IP this season, is beautiful. Adding Hader to the end of the bullpen is a surefire way to lock down games, especially with a setup man like Alzolay, who can step in for save opportunities if necessary. He will cost a pretty penny as a reliever, but Hader is a fantastic fit if you're willing to go over the luxury tax.

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