Not long ago, we wrote a loving post about Adam Wainwright and how it was time for the organization to step up and resign him to a long-term deal, keeping him around in St. Louis for the next several seasons and possibly the rest of his career. At the time, I proposed the Cardinals could lock the tall hammer throwing righty to a deal that went as long as five years and paid out as much as $100 million. The argument I made back then (and this was not even four months ago) was that Wainwright is a premium starting pitcher and deserves to be paid like one. I still agree with that sentiment, but maybe the offseason is starting to get to me; all this constant talk of dollar signs and contracts has me adopting a much more practical outlook on the team’s financial future.

It’s sometimes a different story in the regular season, when our favorite players are on display every summer night, united with each other and the fans in only one goal: to bring the St. Louis Cardinals a victory. The camaraderie that builds between fan and player over the course of each summer is not to be taken lightly, especially when it comes to a player like Adam Wainwright, a player we’ve been watching and admiring since 2006. It’s especially difficult for those of us outside the game to truly place a value on what any one player adds to the clubhouse chemistry, but there’s something about the lanky Georgia native that just feels right. If ever there was a man that exudes what I’d call southern charm, it’s Mr. Wainwright, and perhaps that plays a role in why I love him so much. Okay, it definitely plays a role. Now that the cold, businesslike offseason mindset has crept its way into my thinking, though, I’m not so sure I can stand by the argument I recently made to give this man his money and be done with it. Here’s why.

The first problem is that we can’t even be sure that Wainwright would actually be willing to sign for that proposed amount. The cost of a top flight starting pitcher is anything but cheap in t he current market. Take a look at the recent deals these pitchers have signed and consider the statistical accomplishments they bring to the table:

Zack Greinke (6 years/$147 million) | 2010: 3.34 FIP, 5.1 WAR | 2011: 2.98 FIP, 4.0 WAR | 2012: 3.10 FIP, 5.1 WAR
Cole Hamels (6 years/$144 million) | 2010: 3.67 FIP, 3.7 WAR | 2011: 3.05 FIP, 4.9 WAR | 2012: 3.30 FIP, 4.5 WAR
Matt Cain (5 years/$112.5 million) | 2010: 3.65 FIP, 3.5 WAR | 2011: 2.91 FIP, 5.0 WAR | 2012: 3.40 FIP, 3.8 WAR
Anibal Sanchez (5 years/$80 million) | 2010: 3.32 FIP, 4.4 WAR | 2011: 3.35 FIP, 3.8 WAR | 2012: 3.53 FIP, 3.8 WAR

Now see where Wainwright ranks on that list. In his last three seasons of work:

2009: 3.11 FIP, 5.7 WAR | 2010: 2.86 FIP, 6.1 WAR | 2012: 3.10 FIP, 4.4 WAR

None of the aforementioned pitchers, not even Greinke, can match up to the WAR total Wainwright has posted over his last three seasons. If I’m Adam Wainwright (and I’m most certainly not, as I’ve never froze Carlos Beltran on a called third strike or had to duck when walking beneath an overpass), I’m eyeing these contracts and looking my lips, and not just because I’m thinking of Pappy’s Smokehouse (that’s one aspect of being Adam Wainwright I could really nail). In fact, I posit that a five-year, $100 million contract would actually be a pretty team friendly deal.

It does seem reasonable that the organization has the ability to sign Wainwright, even if it takes a little more than $100 million. Several contracts will be coming off the books after the 2013 season, which is precisely when his new deal would take effect. In 2013, Chris Carpenter is due $12.5 million, Beltran is due another $13 million, Rafael Furcal will earn $7.5 million, and Jake Westbrook takes home $8.75 million. There’s a chance that the Cardinals won’t be paying any of those players in 2014, although there is an option on Westbrook’s deal that will cost them $1 million not to pick up.

Should the team want to pay its best starting pitcher to hang around a while longer, the financial resources appear to be available, but is it wise to do so? If there’s one area the Cardinals appear to have plenty of depth, it’s starting pitching. Assuming Jaime Garcia decides not to let his recent injury woes end his career, the team still has several internal options to fill out the 2014 rotation. By then, Shelby Miller should have had a whole season to establish his role as a perennial Cy Young contender, Trevor Rosenthal may have graduated from his current assignment of death bullpen arm, Lance Lynn could be a solid number three type, and the last spot could go to any number of organizational projects of short-term veteran insurance options. It’s also possible that Carpenter may still have a few cheaper years left in him in 2014, although obviously that’s a bold prediction.

There are still prospects in the pipeline, too. Carlos Martinez may not make it as a starter, but he’s got ability for sure, and he may not be far away by 2014. There’s also the intriguing Seth Maness, who still doesn’t know what it feels like to walk anyone. Ultimately, neither pitcher may pan out, but the possibility does exist. There’s also Joe Kelly, who can’t get left-handers out and probably shouldn’t be a starter, but if he’s put in the number five role, you could do worse. Essentially, the organization may already have their future starting rotation in place, and paying big bucks to Wainwright may be nothing but a pretty expensive solution to a problem that doesn’t exist.

There’s also the fact that Wainwright didn’t finish off last season very well. His fastball velocity over the full season was easily the lowest it’s ever been since 2007, the first time Pitch f/x data was made available at FanGraphs (before then, velocity was something we only guessed at, as in: wow, that fastball really seemed to get to the plate at least a tenth of a second faster on that delivery!), and while it wasn’t a huge difference, it could still point to Wainwright not being quite the same pitcher he was in his two best seasons. Then again, there’s always that possibility that missing the entire 2011 season due to having Tommy John surgery playing a (temporary) role as well. What if the Cardinals take that chance, blow Wainwright away with a bunch of money, and then find he’s already on a downward trend, though? Is that a worthwhile risk with all the pitching depth inside the organization?

For whatever reason, I’m no longer certain this is a deal that needs to be made, and it’s probably fortunate I feel that way. The fact that we’re hearing almost nothing at all about contract discussions indicates to me that John Mozeliak is in no hurry to work something out. My instincts tell me that if locking up Wainwright were truly a top priority for the team (as it was for Yadier Molina a year ago), it would already be done. It’s starting to look like Wainwright be in fact not be around much longer, and while this is certainly a sad development, I think I can easily see it in a positive way; that money can instead go to middle infield and other areas of concern. Then again, it’s easy to say all this in December. Ask me again when Wainwright flashes one of his aw shucks smiles and snaps off a gorgeous curveball or two in April — I’ll probably change my mind on the subject yet again.

Tagged: Adam Wainwright, MLB Contracts, St. Louis Cardinals