Cubs’ Alex Bregman Regret Looms Large as Top Insider Makes Major Prediction Despite Stellar Roster

The Cubs had the chance to cement themselves as National League contenders this offseason. They added firepower to the bullpen with Ryan Pressly, Ryan Brasier, Eli Morgan, Cody Poteet, and Caleb Thielbar. They swung big for Kyle Tucker, giving them a premier left-handed bat to anchor the lineup. This team is deeper, stronger, and undeniably better than last year’s squad. But one name still lingers in the minds of Cubs fans: Alex Bregman.

Chicago pushed for the star third baseman, offering $115 million over four years. Bregman reportedly had the Cubs and Red Sox at the top of his list, but Boston’s $120 million over three years—even with significant deferrals—won out. Just a $5 million difference, yet the impact could be massive.

Instead, the Cubs still don’t have a reliable answer at third base. Nick Madrigal and Christopher Morel remain options, but this isn’t just about glove work. Bregman’s bat remains one of the most disciplined in the game, something the Cubs could have used in a division that won’t be a cakewalk. And MLB’s insiders concur.

Cubs look much improved (deeper pen, Tucker) but missing on Bregman and reluctance to spend like they should hurts,” said Jon Heyman on X. Adding Bregman would have transformed Chicago’s infield into the best defensive unit in baseball. Imagine a Gold Glove trio of Dansby Swanson, Nico Hoerner, and Bregman. That’s a dream scenario for Cubs pitchers and a nightmare for opposing hitters!

Jed Hoyer has spent wisely, but has he spent enough? Trading for Kyle Tucker signals a commitment to winning, but passing on Bregman suggests a limit to their aggression. This wasn’t a case of being outbid by a desperate team throwing reckless money at a star. It was a slight difference, a small gap that the Cubs chose not to bridge. And in a year where they’ve proven they’re serious about competing, it’s fair to ask: why stop just short?

Can Madrigal or Morel fill the void in the Cubs lineup?

With Alex Bregman off the table, the Cubs are left hoping that Nick Madrigal or Christopher Morel can step up at third base. Madrigal plays with a style that focuses on making contact and avoiding strikeouts while also showing defensive skills; however, his potential is limited by his lack of power. He is a great player but may not pose a significant threat in a lineup that already has many contact hitters. In contrast to Madrigal’s strengths and weaknesses, Morel brings to the table raw power and enthusiasm but challenges with defense at third base are cause for worry. His inconsistency with routine plays could become a problem, especially in tight postseason games.

The Cubs could platoon the two based on matchups, but neither option comes close to what Bregman would have provided—elite defense, disciplined at-bats, and proven postseason experience. Unless Morel makes a significant defensive leap or Madrigal starts driving the ball with more authority, third base could remain the weakest link on an otherwise strong Cubs roster. If the team is serious about contending deep into October, they may need to explore a midseason trade to solidify the position.

In the end, the Cubs have built a playoff-worthy team, but if third base becomes a weakness and they fall short in October, fans will have a clear question—why didn’t they go that extra step? Because Bregman in a Cubs uniform? Now that could have been the move that made them a World Series team.

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