Baseball teams, even more than their football or basketball counterparts, most contend with significant negative consequences when swinging and missing on long, large contracts doled out to aging veterans. NBA and NFL teams control their draftees for a total of four years. MLB teams control theirs for up to six at the major-league level — three at the league minimum, three with arbitration rights. This makes it easier to fill a roster with younger, cost-controlled players—and dries up the market for said veterans.

Furthermore, teams that sign a big-time free agent (i.e., those that received and rejected a qualifying offer) are also forced to give up their upcoming first-round draft pick to the player’s former team. This doesn’t happen in other sports, and it compounds the pain of an acquisition bust. Not only are you possibly overpaying for a player who will be worse than expected, you’re giving up a first-round pick for the privilege to do so.

The result has been a lengthening of the free agency period. Two years ago, Kyle Lohse signed with the Brewers during the last week of March for three years and $33 million, after seeking more in free agency and nearly rolling snake eyes. In 2014, Kendrys Morales and Stephen Drew didn’t get deals done until after the season had already started — both gambled and lost by declining their qualifying offer.

Max Scherzer, who is three years younger than Shields, waited until late January to reach an agreement with Washington. Jon Lester’s deal with Chicago—for $25.8 million a year—was made official in mid-December. Ervin Santana, Brandon McCarthy, and Francisco Liriano all found homes, for lower price tags than Shields was been seeking.

All of which begs the question: Why didn’t #TeamShields temper its length and/or salary expectations back in mid-January, when Nightengale leaked that info? The answer is probably simple — this is Shields’ last, best chance to get paid after years of being underpaid.

If we accept the six-million-per-win exchange rate, Shields was paid as a two-plus WAR player last year. The year before that, he was paid as a win-and-a-half player. During 2011, Shields’ finest year from a performance standpoint, he was paid just $4.25 million—despite posting a WAR of 5.2. That’s less than a million bucks per win!

In Shields’—and his agents’—mind, baseball owes him that money for what he’s done throughout his career. The problem is, no team wants to foot the bill. Sure, it’s possible that Shields — what with his elite changeup and throwback-style endurance — could prove an exception to the rule of pitcher decline, but the reality is that no general manager wants to be the next Ruben Amaro—mired with an aging, expensive roster and a bare-bones farm system from which to supplement it.