Adam Wainwright is owed $12 million in 2013, the final year of a two-year club option stemming from an original four-year deal in 2008. Now, the Cardinals are in a predicament: should they extend his contract immediately, giving him no chance to enter free agency following the 2013 season? Or should they risk letting him go onto the free market, where it will most likely cost a fortune to keep him for 2014 and years beyond?

Just to review, here are some of the biggest deals that free agent starting pitchers have signed this off-season:

Zack Greinke: 6 years, $147 million, Anibal Sanchez: 5 years, $80 million, Edwin Jackson: 4 years, $52 million, Jeremy Guthrie: 3 years, $25 million, Ryan Dempster: 2 years, $26.5 million.

Based on the numbers, I think it’s fair to say that assuming he performs reasonably well in 2013, he would be able to get at least a 6 year/$100 million offer.  Is it worth it to his extend his contract now? Wainwright has maintained for a while that he wishes to stay in St. Louis, as he said back in November:

“In brief talks with (Cardinals executives) they feel real good about me coming back for a long time, and I want to make that happen,” Wainwright said. “I don’t see any reason why we shouldn’t make that happen. … It’s not like I have one foot out the door (to free agency). If I’m being honest, they have to show they respect what I’ve done and what I will do. And they have. They have. So I don’t think it will be a problem.”

There is no doubt that Wainwright has been one of the best starting pitchers the Cardinals have had in recent memory: In his 7 seasons with the Cardinals (don’t forget he was out for 2011 because of Tommy John Season), he has gone 80-48 with a 3.15 ERA. But is the money worth it? As we saw last offseason with Pujols, John Mozeliak does not have the same type of payroll flexibility as some of the other major markets, and if the money is more important to the player, which it often is, then it is not unreasonable to think that this might be Wainwright’s last season as a Cardinal. If Mo can extend a reasonable contract to him now before the 2013 season starts, go for it. He is still only 31 years old, and I’d love to think he still has several strong years ahead of him. But if it’s going to cost him over 100 million dollars and it prevents him from going after other players in the future or potentially securing the futures of younger pitchers like Trevor Rosenthal or Shelby Miller, then it unfortunately may be time to part ways. Let’s hope that it’s the former that happens.