Who The Cubs Should Target Between Bellinger And Bregman

The Cubs have a history of sorts with both Bellinger and Bregman. Bellinger played two years with Chicago before he was traded last offseason to the Yankees so that the Cubs could acquire/afford Kyle Tucker.

Bregman, on the other hand, has never played in Chicago, but the organization found itself in the same bidding war that it is in now with him during his last free agency at the end of 2024. The Cubs wouldn't sign both of them, so who should they be pursuing?

Ultimately, there are clear reasons that Bellinger should be the main target over Bregman. First, they already know what they are getting with Bellinger. Second, Matt Shaw is poised for a breakout season. And third, the Edward Cabrera trade thinned their outfield options.

Bellinger is the devil they know

The 30-year-old spent two seasons with the Cubs before joining the Yankees, and he was better than Tucker in both years. Tucker finished 2025 with 73 runs batted in and 22 long balls, which earned him his second Silver Slugger Award.

Bellinger, in his season in New York, finished with 29 home runs and 98 RBI. Acquiring Bellinger would ultimately be the right move, adding a proven bat who has hit no worse than .266 in the last three years.

Signing Bellinger will also keep Seiya Suzuki at designated hitter, making it so that rookie Moises Ballesteros doesn't have to be counted on at DH if Hoyer is trying to build a "win now" roster.

Matt Shaw ready to break out

Jed Hoyer has expressed his positive viewpoint on Shaw after he found success after the All-Star break, where his entire slash line improved. Remember, this was only his rookie season, and he went from batting under .200 to .258 in his final 63 games, while his OPS rose from .556 to .839.

It is also hard to ignore that he was named a Gold Glove finalist in just his first year of service for the Cubs, who have arguably the best all-around defense in the league. Hoyer and Craig Counsell both pride themselves on their defense, and Shaw fits the mold.

Outfield replacement needed

There was a consensus that Caissie (former No. 1 Cubs prospect) was going to be stepping in to embrace his rookie season, but now he will be suiting up for the Marlins as the main piece of the deal for Cabrera.

With Caissie leaving, it puts Suzuki back in the outfield and, once again, that would mean they are counting on Ballesteros to take on the lion's share of the work at DH. If he has issues or finds himself in a rut, what then? The outfield is incredibly thin, and signing Bregman won't solve that.

Either way, the Cubs are going to be spending quite a bit of money as the two All-Stars are looking for major deals with whoever they sign with. It should be Bellinger that they reunite with as the final piece to their 2026 roster.