Adam Wainwright contract talks continue, but how much is too much?

With Jason Motte signed (for two years for some reason) and the rest of the St. Louis Cardinals' 25-man roster seemingly in place, we're left to discuss what will either be the Cardinals' first $100-million contract since Matt Holliday or their first vanishing fan-favorite since Albert Pujols. B.J. Rains summarized the run-up to the negotiations on Tuesday, and believes they'll continue in earnest heading into Spring Training. Meanwhile, the two questions are the same as they've been all offseason:

1. What will Adam Wainwright cost? The most unavoidable recent comparisons have come courtesy Matt Cain, who replaced the last year in his old contract with a six-year, $127.5 million deal with the San Francisco Giants before the 2012 season, and Zack Greinke, who signed for six years and $147 million with the Los Angeles Dodgers last month.

That's a lot of money—both contracts are larger than Holliday's over fewer years.

2. How long will he be around? Greinke is two years younger than Wainwright—the first year of his new deal will be baseball-age-29—and Matt Cain was even younger, signing his contract ahead of his age-27 season. I think it's important that both contracts stop short of the psychological seven-year barrier; teams could (and maybe should) be moving toward high-AAV, shorter-term deals for pitchers relative to top position players.

Wainwright's deal is squeezed on the other end, though, by the five-year, $88 million deal the Detroit Tigers gave Anibal Sanchez (29 in 2013.) Sanchez has an extremely checkered injury history—he made 32 starts between 2007 and 2009—and has never topped 3.5 rWAR in a season; the price of young, above-average free-agent starters is pretty high.

I don't think Wainwright will or should get six years, but his AAV seems destined to approach Cain and Greinke levels.

3. Do the Cardinals have any leverage? Does Wainwright? Wainwright's too good to worry about the qualifying-offer hysteria that's crushed Kyle Lohse's value, and he's set to make $12 million this year. He explained it himself, in his usual endearingly straightforward way, to Derrick Goold over the weekend:

"I'm in a different place now," Wainwright explained Saturday. "The first contract is real important to players (to) get some security, peace of mind. It was all a new thing for me. Those kind of things I was worried about back then, I don't really worry about those any more."

Which is a really effective summary of the way things have worked, post-Longoria, in Major League Baseball. Teams give players financial security in exchange for an often-significant discount on some of their most valuable years, and players come back with that security, a few years later, as leverage for their next deal.

What makes this an interesting contract, though, is the last year remaining on Wainwright's current contract. Coming off what looked like a down year, both sides face significant risks in letting him get all the way to free agency. Who'll blink first? Who should?

Further reading: Last month, bgh wrote about Adam Wainwright as a trade candidate; in November, tom wrote in more detail than I just have about Wainwright as an extension candidate.