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.