It was reported late last night that Alex Bregman reached a consensus agreement with the Chicago Cubs and will be signing a five-year, $135 million deal. What a payday for one of the best third basemen in the league—and finally one that gives him long-term security. A ten-year veteran with over 40 WAR, Bregman has collected 1,250 hits, 758 runs, 725 RBIs, 191 home runs, 627 walks, and owns a career slash line of .272/.365/.481/.846 with a career 132 OPS+.

Bringing Alex Bregman to Chicago only makes their lineup stronger and puts them in consideration as one of the best in the league, if not one of the top contenders for the World Series. A lineup featuring slugger Michael Busch at first base, defensive wizard Nico Hoerner at second, Bregman at third, Dansby Swanson at shortstop, followed by one of the best two-way center fielders in the game in PCA, a solid bat in Ian Happ, and one of the best offensive Japanese hitters not named Shohei Ohtani in Seiya Suzuki anchoring the outfield and DH is flat-out dangerous.

This lineup is potent and packed to the brim with talent. And when you pair it with a pitching staff led by newly acquired Edward Cabrera, it only makes you wonder how far these Cubbies can go in the 2026 season.

But while one general manager is ecstatic about landing Bregman, another is left speechless after losing one of the game’s best. That brings us to the loser of this whole situation: Craig Breslow.

Craig Breslow, the general manager of the Red Sox, pulled off the “jack of all trades” last offseason when he signed Bregman to a three-year, $120 million deal with opt-outs. The idea was simple: pair Rafael Devers and Alex Bregman on the same infield, with Bregman expected to play second base and Devers remaining at his primary position at third.

Then spring training happened. It was reported that the Red Sox planned to move Devers to DH and make Bregman their everyday third baseman. What seemed like a fantasy-turned-reality quickly shifted into a PR nightmare when Devers refused the change. Next thing you know, Devers is shipped to the Giants, and the expectation becomes that Boston will lock in Bregman long-term. Instead, he opts out, leaves for Chicago, and now the Red Sox are stuck with no Devers, no Bregman, and zero internal replacements of equal caliber at third base.

There’s no need to recount every step—the point is that Craig Breslow gambled and lost. After a year with two of the best offensive third basemen in the league, he created unnecessary trouble by moving Bregman to third instead of simply keeping his original plan and playing him at second, which he was fine with. Now, Breslow will have to rely on internal prospects to play third, which I suppose he valued more than giving Bregman a no-trade clause.

It was reported that the Red Sox offered Bregman a five-year, $165 million deal with escalators up to $205 million for six years, but refused to include a no-trade clause. That was the only clause Bregman wouldn’t budge on, and it ultimately led him to take his talents to Chicago.

It’s an unfortunate masterclass disaster with two sides to the story. It’s typical baseball—no one can be satisfied, and someone is always upset by another team’s move. The bigger point is that if you’re cheap, and you refuse to structure contracts in a way that respects the player, not just the “asset,” then you shouldn’t be shocked when the player leaves. Baseball is a business at the end of the day, and at the end of the day Bregman loved being a Red Sock, but he wanted security and not to worry about being traded at any moment.

You won’t please everyone, but if you make “conscious financial decisions” without considering the player, you’re going to finish third every single time.