Chicago had a chance to end its offseason with a star acquisition, but failed to get the deal done. Here's why it was such a troubling outcome for the big-market franchise.

The Cubs have tried to get creative with contract structure in order to compete while also avoiding uber-long deals. They won the Cody Bellinger sweepstakes last year, for example, by front-loading his three-year, $80 million deal and including two opt-outs.

Cubs president of baseball operations Jed Hoyer made his case to ownership that this was the right moment to pursue star free agent Alex Bregman for third base, and received the green light. In the end,