Top Five: Largest St. Louis Cardinals Contracts

Ah, December. It's that time of the Hot Stove season when enormous free agent contracts come out of the ground and tell us whether or not we'll have six more weeks of complaining about increasing baseball payrolls. It turns out that in 2011 we will! Jayson Werth's enormous deal with the Washington Nationals was the first sign that salary inflation was back on the job, and Carl Crawford's pact with the Boston Red Sox was the inevitable conclusion. But Cliff Lee's bargain signing with the Philadelphia Phillies, who seemed completely tapped out a few weeks ago, puts the pressure back on the St. Louis Cardinals, who are stepping tentatively toward the eventuality that Albert Pujols will be the highest-paid player in baseball. 

Until Pujols and the Cardinals finally negotiate about something other than when they'll negotiate, though, these remain the most expensive contracts on the St. Louis Cardinals' books.

1. Matt Holliday: Seven years, $120 Million, 2010-2016

Since Crawford and Werth went for $142 million and $126 million, respectively, Matt Holliday might end up a relative bargain by the time his contract runs out. But this time last year it was a major restructuring of the organization's long-term plans, and a clear push from their post-Jocketty youth movement toward a hybrid model built around some massive contracts and young players who could provide value on the cheap. 

With Pujols' extension looming over the Cardinals' future whether he signs one or not, the Cardinals' ability to stick to this strategy will finally be put to the test. But through one year, at least, the Cardinals have gotten what they paid for — Holliday's OPS+ in 2010 was the second-highest of his career.

2. Albert Pujols: Seven years, $100 Million, 2004-2010

Seven years seemed like such a long time in 2004. Albert Pujols had just hit .359 in his age 23 season, the Cardinals were about to win 105 games, and their most expensive player was Matt Morris, who was making $12.5 million. Matt Morris! 

That 2004 team was pretty top-heavy, though, in hindsight. The Cardinals had seven players making $7 million or more that year — Morris, Jim Edmonds, Scott Rolen, Woody Williams, Jason Isringhausen, Edgar Renteria, and Pujols. Chris Carpenter and Tony Womack were the only major contributors to those 105 wins to make less than a million dollars.

By contrast, the new Cardinals model is built around megacontracts and team control. The Cardinals had three starters and three relievers making less than $500,000 last season, but their top three contracts were worth nearly $50 million; in 2004 the MV3 cost a combined $25 million. 

3. Chris Carpenter: Five years, $63.5 Million, 2007-2011

That's a nice discount on a pitcher who'd put together two consecutive Cy Young-caliber seasons, but there was just one problem with this deal from the beginning: The Cardinals already had Carpenter signed to a better one.

Following his Cy Young season in 2005 the Cardinals signed their new ace to an incredibly team-friendly two-year, $13 million deal with an $8 million club option for 2008. That's right: The Cardinals had two years to work out a long-term extension with Chris Carpenter. That's also right: Those two years were the ones he missed after elbow problems cropped up during the first start of his new $63.5 million contract. 

Carpenter's been great in the two years since he returned, but I can't imagine he would have cost $43 million between 2009-2011 if he'd hit the market following his second consecutive season on the disabled list. 

If they had to start negotiating with a guy two years too soon, couldn't it at least have been Albert Pujols?

4. Kyle Lohse: Four years, $41 million, 2009-2012

There was just one problem with this deal from the beginning, too — that the Cardinals had given it to Kyle Lohse. Forget about Mozeliak rushing to get this deal done about a month before the bottom dropped out of the economy, baseball and otherwise. Forget about Kyle Lohse's secret predilection for motocross accidents, and his subpar 2009 and awful 2010. 

The Cardinals signed Kyle Lohse to a $41 million contract in the hopes that, at ages 30 through 33, he would repeat the best season he'd ever had four more times. I didn't expect it to blow up in their faces so completely—thus far he's been worth a combined 3.6 wins below a replacement level pitcher, according to Baseball-Reference, leaving him among the least-valuable players in baseball over that timeframe — but the Cardinals signed Lohse to a deal that left no margin for error from the beginning. 

5. Jake Westbrook: Two years, $16.5 million

What's great about the Cardinals' fifth most expensive contract is that in terms of guaranteed money it's not Adam Wainwright; for all the complaining that can be done about Carpenter and Lohse's long-term deals, the maneuvering John Mozeliak and the Cardinals did to sign Wainwright to a long-term deal all the way back in 2008 is beyond reproach.

Jake Westbrook is a little closer to market value—Jon Garland's one-year, $5 million contract with the Los Angeles Dodgers made everybody look a little expensive—but the team's decision to pick up a third year in the form of a mutual option is what makes it so much more attractive than its cousin the Lohse deal. Westbrook might have gotten a guaranteed third year someplace else, but that doesn't mean he should have; it's difficult to justify signing a player to a three-year contract when he's played one year out of the last three.