Todd Helton, $141.5 million (2003-2011)
Early in his career, Helton looked like the second coming of Coors Field mashers, bashing at least 30 homers in each of the four seasons prior to this contract taking effect and posting some absolutely silly slash lines. Of course, this contract began mere months before he turned 30, and Helton hit a wall not even halfway through the extension. He hasn't had a 20 homer season since 2005 (when he hit exactly 20), and he's gone from "elite" to "average" in an extremely quick time period.
Albert Pujols, $100 million (2004-2010)
The Cardinals giving this extension to Pujols is the best bargain on this list. In the seven years during this contract, Pujols gave the team 59.1 wins of value, won three MVP awards, and helped the Cardinals to the 2006 World Championship. St Louis won the 2011 World Series after exercising an option on Pujols for that season, and then let him walk to the Angels, where the money in his contract doubled just in time for Pujols to put together the worst season of his career in 2012. This contract that the Cardinals gave him worked out extremely well for them, as they paid an average of $14.3 million per season for no less than 7.5 wins a season. Just insane.
Carlos Beltran, $119 million (2005-2011)
Beltran is often bashed to hell by Mets fans because of his contract, but after struggling in the first year of the deal, he was awesome from 2006 to 2008, totaling 21 fWAR. But then, he got hurt and missed half of 2009 and 2010 before rebounding to play a full 2011 season and getting dealt to the Giants at midseason for top pitching prospect Zack Wheeler. Based on how some of the contracts on this list turned out, the Mets could have done a lot worse with Beltran's deal. His knee issues in 2009 and 2010 took this train off the tracks, but the Mets got insane peak value out of him.
Carlos Lee, $100 million (2007-2012)
This contract didn't make much sense when it was signed, and it doesn't make much sense now. Lee contributed 10.5 wins above replacement to the Astros over the life of the contract, homering 30 times in just the first year of the contract after four straight 30 homer seasons going into it. Houston never finished higher than third in the NL Central over the life of the contract, and finished above .500 just once. So....how'd that go for you, Astros?
Alfonso Soriano, $136 million (2007-2014)
The Cubs are still dealing with this disaster, and the Soriano they've gotten is nothing like the player who had a 40/40 season with the Nationals in 2006. In fact, Soriano doesn't even have a 20 steal season with Chicago, and has just two 30 homer seasons. Washington turned Soriano from a butcher at second base into a fantastic left fielder, but his defensive ability has deteriorated in his later years. In his six years as a Cub, Soriano has had one fantastic season, three good ones, one bad one, and one disaster. Thankfully, the Cubs are still bringing in money hand over fist, so it's not as if the organization is under a threat of relocating or anything along those lines.
Barry Zito, $126 million (2007-2013)
Zito's Giants career has been a mess. He's never thrown 200 innings in a season, he's never had an ERA below 4.00, and he's had just one season where he's been worth 2.0 fWAR. But yet, the Giants have won a pair of World Championships with Zito on the team, and have finished above .500 in each of the last four seasons. If Zito's role on the team was to be the top of the rotation ace while he's surrounded by a cadre of league average pitchers, there would likely be an overwhelming amount of animosity towards Zito and his contract. But with Matt Cain and Tim Lincecum both in the fold, Zito can take a less important role with the team and focus on being that league average pitcher that the team could use behind their aces. Besides, flags fly forever, and the Giants have raised a pair of them in the last three years while paying Zito his mint.
In summary, what does this mean? Well, more often than not, handing out large contracts don't end well for teams. They have a better chance of working out if the player is younger than 30 though, which is something that teams courting Josh Hamilton, Michael Bourn, and Mike Napoli should keep in mind this winter.
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