Red Sox might circle back to past Cubs deadline prize after Alex Bregman strikeout

The Chicago Cubs went above and beyond to lure Alex Bregman out of Boston, handing him the highest AAV in franchise history (and a full no-trade clause) to convince him to spend the remainder of his prime in the Windy City.

Their lineup figures to receive a big boost from the third base position after Matt Shaw's inconsistent rookie year, and Bregman should seamlessly slot into Kyle Tucker's vacated spot in the middle of the batting order. There figure to be long-term consequences to handing a soon-to-be 32-year-old $35 million per year, but in the immediate future, the Cubs should be much better with their new star in the fold.

Of course, on the flip side of all of this is that the Red Sox are now without any semblance of answer for their opening at third base. That spot was meant to be occupied for the foreseeable future by Rafael Devers, but he was dealt after being displaced by Bregman... who now left for the greener pastures of Wrigley Field. Yikes. Former Cubs executive Craig Breslow definitely wishes he could go back and do all of this over again, I'm sure.

With no way of going back in time to correct their mistakes, the Red Sox must now look forward. And, per Chandler Rome of The Athletic, their attention may be diverting toward a former Cub.

Red Sox reportedly targeting Isaac Paredes after losing Alex Bregman

Isaac Paredes was originally brought to Chicago in a 2024 trade deadline deal with the Tampa Bay Rays that saw fan favorite Christoper Morel head back to Florida. The deal didn't work out great for either side — Morel is now with the Miami Marlins after signing a one-year deal in free agency — though it did ultimately lead to the Cubs scooping up Bregman.

After posting an 85 wRC+ with just three home runs in his half-season with the Cubs, Paredes was one of the centerpieces in the deal that brought Kyle Tucker to Chicago. The 26-year-old third baseman, who has two years of team control remaining, did perform better in Houston, blasting 20 home runs while recording a 128 wRC+ in 2025.

As one of the most pull-heavy hitters in the league, Paredes would feast in Fenway Park taking aim the Green Monster. After losing another replacement option for Bregman once the St. Louis Cardinals dealt Nolan Arenado to the Diamondbacks, Paredes could be Breslow's best bet to handle the hot corner in 2026.

Still, he can't come close to approximating the value Bregman brings to the table. I guess they should have included that no-trade clause after all.