Is this the year the St. Louis Cardinals go upside down on Matt Holliday?

When people, post-FanGraphs, talk about the way big-ticket free agent contracts are supposed to work, they're talking about the one Matt Holliday and the St. Louis Cardinals agreed to in 2010. A star near the top of his game signs a long, gaudy-looking contract, and the team stands to benefit—despite the specter of those last few seasons—on account of:

1. Something something inflation at the end and

2. Surplus value at the beginning,

such that you're not relying on Matt Holliday to be worth $17 million as a 37-year-old, though nobody in the front office would complain if he were.

People on FanGraphs might, though, simply because the Holliday contract is so right right now. $120 million is already starting to look a little quaint, and through three seasons Holliday has already deposited 16 wins above replacement—$67.6 million, by FanGraphs' valuation.

Accept that, then, and he's already nearly a season ahead of his actual $17 million a season price-tag.

That's exactly how it's supposed to work. But now Holliday's 33, and as of a couple of weeks ago we're officially in the back half of that contract—where he's supposed to decline while the Cardinals look on benignly, contented by the sheer fairness of the thing.

Holliday, who's always seemed so eager to please, has risen to the occasion by drifting toward his worst season since 2004. Using FanGraphs' more optimistic estimation of his value to date, he's still on pace to fall about $3 million below the value of his contract, which'll be the first time in his career a team's been upside down on him.

Holliday, like Albert Pujols before him, plays in such a way that he always seems to be either in intense pain or putting himself in a situation that will result in intense pain; because of that I'm reluctant to assume the worst after 78 games. But if we got the worst, what would that do to the perfect aesthetics of the Holliday deal? Has he built up enough slack to limp over the $120 million mark?

He's $38 million of value away from $120, and he's got roughly $51 million more coming to him, so—maybe.

If he were to hold at the level where ZiPS projects him to finish this year, firmly in above-average-regular territory, he'd finish the contract with $4 million of surplus value left over, from a peak of $16; the FanGraphs method couldn't ask for a better example case. But he hasn't quite squirreled away enough WAR to decline league average this soon.

Which illustrates, I think, both the usefulness and the brittleness of these concepts. WAR valuations have given us a clarity that used to be totally absent from long-term contract discussions; for me it's already difficult to remember how we talked about these deals without it. But when it actually comes time for these frontloaded-value contracts to wind down—even the most perfectly formed example in baseball—they're the start of the was-he-worth-it discussion, not the end of it.