With the benefit of 20-20 hindsight, it’s apparent that James Shields reached the zenith of his negotiation leverage on the night of Dec. 9. That was the night when Jon Lester finalized his decision to go to the Chicago Cubs, and the San Francisco Giants and other teams faced the reality that they needed a Plan B.

Shields was in a good spot in that moment, it seemed, because unlike Cole Hamels, he wouldn’t require a trade investment of prospects, and unlike Max Scherzer, he wouldn’t require the equivalent of a Defense Department budget to sign. Whatever cards Shields held at that time were probably the best he has seen all winter.

But that leverage is now gone, and Shields is in the worst possible spot of any free agent, when most teams are finished spending for the winter and more readily identify reasons to dismiss an available player. In Shields' case, the loudest concerns are about his age (33), his heavy workloads (eight straight seasons of 203 or more innings pitched), his need for a ballpark that forgives his tendency to surrender fly balls to left-center field; his home games have been in the pitcher-friendly Tropicana Field and Kauffmann Stadium, and he has a career ERA of 5.42 in Fenway Park.

The longer a premium free agent like Shields remains unsigned, the more his negotiating strategy and leverage position gets picked apart. As we move into February, some executives have become convinced that while Shields was an interesting alternative on Dec. 9, he is now hurt by looming market alternatives.

“If you’re in a position where you’ve got money to spend, would you rather jump at Shields, or wait?”