The Chicago Cubs have oddly opted for a conservative approach in trying to sign Alex Bregman by offering him a three-year contract. Whereas other teams such as the Detroit Tigers and Boston Red Sox, along with the Toronto Blue Jays and Houston Astros, have put forward a six-year deal. This cautious tactic has drawn criticism as a former champion from the 2013 World Series, Ryan Dempster, has advised them to reconsider their inflexible plan.

Bregman, 30, remains one of the premier third basemen in the game despite a slight dip in offensive production last season. Adding his top-notch skills and seasoned leadership to the mix would boost the Cubs lineup that already includes former Astros standouts Kyle Tucker and Ryan Pressly. But their hesitation to agree to a long-term contract might jeopardize their opportunity to strengthen their infield and secure a victory in the NL Central division race.

Cubs’ Hesitation in Bregman Pursuit Raises Eyebrows

According to a recent MLB Network X post, World Champion Ryan Dempster talked about Alex Bregman’s potential addition to the Cubs. He said, “It’s a place (Cubs) that Alex Bregman would love to play if not back in Houston. If that’s something that comes to fruition, I think it really solidifies the Cubs as a frontrunner in the National League Central.”

He further urged the Cubs to expand their thinking. The message is clear: stop fixating on short-term contracts and recognize the impact a player like Bregman could have over the next several seasons.

Jed Hoyer and Carter Hawkins have steered the Cubs toward a methodical, calculated approach to free agency. While their patience has worked in some cases, such as their blockbuster trade for Tucker, it now risks backfiring with Bregman. Chicago seems intent on waiting for the market to cool, betting that Bregman’s price will drop. However, teams like the Tigers, who could reunite Bregman with A. J. Hinch, or the Red Sox, who might use him at second base, remain aggressive.

If the Cubs land Bregman, he would immediately transform their infield and lineup depth. Meanwhile, prospect Matt Shaw, an exciting young talent, would benefit from additional development time rather than being thrust into a starting role on a contending team. The Cubs would be securing a proven veteran while allowing their future star to mature.

Despite his offensive dip, Bregman’s bat still projects well at Wrigley. A return to a .270 average with 25 homers and 90 RBIs is realistic, and his Gold Glove defense would be an asset for a team looking to compete deep into October. The Cubs are clearly interested, but their reluctance to match long-term offers could push Bregman elsewhere.

How Bregman’s Arrival Affects Matt Shaw’s Development

Baseball is full of stories where young talent is thrown into the deep end too soon—sometimes they swim, but often they sink. Matt Shaw, the Cubs’ rising infield prospect, is an electrifying hitter with immense potential. However, expecting him to anchor third base for a contending team on Opening Day could be a risky bet.

Alex Bregman could allow Shaw to develop at a more natural pace, reducing the pressure on him while refining his defensive skills and approach at the plate. Instead of being force-fed big-league at-bats before he’s fully prepared, Shaw could learn from one of the best third basemen of the past decade. Think of Bregman as the bridge, not the blockade.

Having an established veteran in place gives the Cubs options—Shaw can refine his game in Triple-A or transition to second base if his defensive profile fits better there long term. On the other hand, Bregman would bring consistency to the lineup and valuable playoff experience, both crucial for a team aiming for success.

Ultimately, the Cubs don’t need to make a decision between what lies in the future and what’s happening now. Signing Bregman allows them to strengthen both, ensuring Shaw isn’t just ready for the majors but ready to thrive.