Cubs’ free agency regret set the stage for the Rafael Devers trade

The argument could be made that the Chicago Cubs set the stage for the Boston Red Sox to trade Rafael Devers. At the center of the decision for the Red Sox was the fact that they were successful in their pursuit of Alex Bregman this past offseason. At the time, the Cubs were making a push to sign Bregman, with the idea being that the front office was aware of the opportunity in front of them. Nevertheless, the Red Sox were the victors of the Bregman sweepstakes.

Had the Cubs signed Bregman, chances are Devers would be waking up on Monday still with the reputation of being the beloved Red Sox superstar. Instead, the Red Sox's decision to sign Bregman backfired almost instantly when it came to the impact it had on Devers' relationship with the team.

Craig Breslow, the former Cubs' exec turned Chief Baseball Officer of the Red Sox, never quite communicated the plan to Devers. Had Breslow told Devers about the potential move to designated hitter ahead of signing Bregman, chances are the two sides would have been able to work out their difference. Instead, the relationship was frayed and only got worse during the season.

Cubs missing on Alex Bregman indirectly led to the Boston Red Sox trading Rafael Devers

In a world where Matt Shaw did not turn the corner at third base for the Cubs upon his return from the minor leagues, then it would be a safe bet to assume that Jed Hoyer would have been among the executives who checked in on Devers' availability before he was dealt to the Giants. But Shaw has been excellent, especially with his defense at the hot corner.

Larger than Shaw already being at third base, the biggest reason why a Devers trade wouldn't have involved the Cubs is that the Giants are taking on the remaining money on his contract. The math comes out to just over $250MM for the next 8 and a half years. With a potential contact for Kyle Tucker looming and Pete Crow-Armstrong's increasing price, there's not a scenario where the Cubs would have taken on the money remaining in Devers' deal.