The Chicago Cubs enter the Winter Meetings balancing two storylines: Matt Shaw’s breakout at third base and Alex Bregman’s return to MLB Free Agency. The Cubs likes its young core and fans love Shaw’s rise. But Bregman, a three-time All-Star and two-time World Series champion, is back on the market after opting out of the Red Sox and posting a .273/.360/.462 line with 18 homers in 114 games. His name brings weight. His presence shifts conversations. And it forces the Cubs to consider how far they’ll go to add one more proven bat.
Matt Shaw gave the team real clarity last season. He defended well and hit with poise. He handled third base like he belonged under the stadium lights. That’s why the thought of moving him, even for someone as accomplished as Bregman, feels complicated. The Cubs already have Nico Hoerner locked in at second. He’s a leader. He’s an anchor. So the idea of shifting Shaw there creates more questions than answers.
If Bregman signs with the Cubs, where does Shaw fit?
If the Cubs make a splash during the Winter Meetings, Shaw is the player most affected. The front office could explore a rotation between third, second, and DH. They could test Shaw’s versatility. They could entertain trade interest, though that path seems unlikely for now. Or they could decide that competition pushes everyone forward and insist that talent finds its place.
Alex Bregman would upgrade the lineup overnight. His experience lifts a clubhouse. His postseason profile gives Chicago a dimension it still seeks. But the Cubs also proved they could win without him, and Shaw proved he can hold down an everyday job. Those truths collide now, shaping every MLB Free Agency rumor around the team’s next move.
If Alex Bregman walks into Wrigley, how far will the Cubs go to keep Matt Shaw’s future just as bright?
