Alex Bregman contract detail helped Cubs take advantage of Red Sox dysfunction

In many ways, the Chicago Cubs' signing Alex Bregman defied just about every piece of logic the team's front office has applied to decisions in recent years. Instead of waiting for Bregman's market to bottom out, Jed Hoyer and Co. offered him the most overall money and included deferrals to lower the AAV of the deal.

It's just not how the Cubs have operated under Hoyer. Dansby Swanson was one of the largest free-agent deals in the history of the organization, but even that was a case of Chicago settling for a lesser option available.

Shohei Ohtani and Juan Soto are franchise-altering players, and yet, the Cubs were willing to sit on the sidelines. The Cubs refused to include deferrals in their offer to Ohtani, and weren't involved in Soto's bidding last offseason. An offseason where the Cubs identified Bregman as a player they had to have, but didn't have the financial approval from Tom Ricketts to make the strongest offer.

This offseason, the Cubs' misses have been well documented. Dylan Cease was a name of interest, but the Cubs bowed out of the bidding once it reached $200 million.

Cubs took advantage of the biggest issue surrounding the Boston Red Sox over the past year.

It's why there was so much skepticism when talking about the Cubs' interest in Bregman. They weren't shy about expressing their love for him, but history suggested they weren't going to top the Red Sox. Not only did they offer Bregman more money than Boston, but included in his contract something Boston refused to add in their offer.

Mass Live's Sean McAdam highlighted several takeaways from Bregman deciding to play out his career in Chicago rather than Boston. Certainly, money played a factor, but McAdam added that the Red Sox did not include a full no-trade clause in their offer to bring back the All-Star third baseman. It's believed to be an organizational policy, and does little to discredit the loyalty concerns that have surrounded the Red Sox since Craig Breslow took over as the top voice in the front office. A fear that was heightened after the trade of Rafael Devers.

Had the Red Sox been willing to include the no-trade clause, perhaps Bregman would've taken the discounted offer. Instead, after playing with two different teams over the past two years, the Cubs have provided the 31-year-old with long-term security.