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With the signings of Jayson Werth(notes) and Carl Crawford(notes) this past week, there have now been 10 free agent position players who have received contracts of $100 million or more. Thanks to the efforts of Werth, Crawford, and Matt Holliday(notes) in January, 2010 is proving to be one of the most expensive years in the recent history of free agency.

It's the first time since 2006 that three different $100 million contracts were given out in the same calendar year. Unfortunately, the three 2006 deals are three of the worst free agent contracts ever given out: Alfonso Soriano's(notes) 8/$136, Barry Zito's(notes) 7/$126, and Carlos Lee's(notes) 6/$100. Considering that many of these contracts were recently signed in the past few years, it might seem unfair to classify and rank them from best to worst. But every December needs a scrooge, so ... here we go!

Note: This list deals only with free agent position players. So no extensions (think Derek Jeter(notes) or Vernon Wells(notes)) and no pitchers (think Zito and CC Sabathia(notes)).

Relatively Worth It

1. Alex Rodriguez(notes)Texas Rangers 10 years, $252 million (2000)
Technically, Alex Rodriguez has been a free agent twice — he was considered a free agent when he opted out of his contract during the World Series.The deal he signed then could be one of the worst contracts ever, considering that his injury problems and PED admission came shortly afterward. But the deal he signed in 2000 is more interesting. It crippled the Texas Rangers, who simply couldn't afford to spend the money they gave him. But it was eminently reasonable for the Yankees to take over. And his production from 2000 to 2007 merited the money, as he garnered three MVPs and was considered the best player in the league. He was worth more money than the Rangers could afford — but he was worth it.

2. Manny Ramirez(notes)Boston Red Sox, eight years, $160 million (2000)
Manny had an acrimonious departure from Boston, but they more or less got what they paid for. During his time with the Red Sox, he hit .312/.411/.588 during the regular season and .321/.422/.558 in the playoffs, and he was the World Series MVP in 2004 — the Red Sox's first championship since 1918. He was such a butcher in the field that he gave back many of the runs that he produced with his bat; his defensive reputation was so foul that despite his offense he never once finished in the top three for the MVP during the regular season during his time with the team. Still, the Red Sox knew that going in, and though he was an overpaid one-dimensional player, they could afford it. They hired him to hit, and hit he did.

3. Carlos Beltran(notes)New York Mets, seven years, $119 million (2005)
It tells you something about the contracts on this list that, despite his knee microfracture surgery and nearly a year of playing time missed, the Mets' acquisition of Carlos Beltran still rates as one of the least foolish $100 million contracts ever. His first year in New York was disappointing, but his second was the best year of his career, and his third and fourth were two of his best years ever. If he's healthy in 2011, he'll come close to having earned his money despite all the time he missed. Or, at least, closer than most of the other players on the list.

Let's Hope They Stay Healthy

4. Carl Crawford Boston Red Sox, seven years, $142 million (2010)
A few days before Crawford signed his contract with the Red Sox, Rany Jazayerli wrote a blog post detailing exactly why he thought the Kansas City Royals should give Crawford a 7-year, $140 million contract. If Jazayerli's premise is correct and Crawford could be worth that to the Royals, then he certainly should be worth that to the Sox, because good players are worth more to a good team than to a bad team. As sports economist J.C. Bradbury explains:

Wins are worth more to winning teams than losing teams... CC Sabathia was worth about $30 million more valuable to the Yankees over the term of his deal than he would have been to an average team.

Moreover, Tom Tango has found that fast players tend to age more gently than slow players, which bodes well for Carl Crawford's future. If he stays healthy, he has a good chance to be worth the money. But, over the course of seven long years, that's a big if.

5. Matt HollidaySt. Louis Cardinals, seven years, $120 million (2010)
6. Jayson WerthPhiladelphia Phillies, seven years, $126 million (2010)
Matt Holliday is a slightly better, slightly younger version of Jayson Werth, and he received a contract worth $6 million less. Like Werth, he plays good corner outfield defense, has good power and some speed — Holliday has stolen 51 bases in the past three seasons while Werth has swiped 53. He is very likely to be worth the money for the first several years of the contract.

But it's very hard to know how he will weather the ravages of time once he hits his mid-30s. How to predict player aging is one of the more controversial aspects of modern baseball research, especially since many players had non-standard aging curves and played longer careers during the Steroid Era. Holliday and Werth will likely age more gracefully than a plodding old slugger with lead feet — like Carlos Lee, Jason Giambi(notes), or Mark Teixeira(notes) below — and the Cardinals and Nationals will certainly be hoping that turns out to be the case.

Overpaid Role Player

7. Mark TeixeiraNew York Yankees, eight years, $180 million (2008)
No team other than the Yankees could afford to pay Mark Teixeira $180 million to be the third or fourth banana on their team. But it's true: the Yankees' best player is Robinson Cano(notes), their best pitcher is CC Sabathia, and depending on the night, Teixeira could be behind Derek Jeter, Brett Gardner(notes), Alex Rodriguez, or Mariano Rivera(notes) in the fans' affections. His salary is so out of line with his role that Joe Posnanski coined the word "Texpensive" to describe it:

Teixeira will be the third-highest paid every day player in baseball in 2011... Is Mark Teixeira the third-best player in baseball? No. Is he the best first baseman in baseball. No. That's Albert Pujols(notes). Is he second best? Third best? Fourth best? Maybe. But maybe not.

Of course, the Yankees can afford Teixeira if he stays good. But not if he turns into a pumpkin like Jason Giambi did. And last year wasn't reassuring, as Teixeira batted .256 and had his lowest slugging percentage since his rookie year. It was probably just a momentary blip, caused by a temporary dip in his batting average on balls in play, but it was the first season of his 30s, and the Yankees will have to hope for better results during his next six seasons.

Dreck

8. Jason GiambiNew York Yankees, seven years, $120 million (2001)
The Giambino's contract was eye-popping at the time, the third-highest free agent contract ever given out, following Rodriguez and Ramirez's mammoth paydays in 2000. At first, it looked like all would go well, as his first two years with the Yankees were terrific. But then the trouble started. He missed half of the 2004 and 2007 seasons and all but admitted to steroid use (with his famous "I'm sorry" not-a-confession) in 2005. He averaged 117 games a year over the last five seasons of his contract, with good but not great production. It's impossible to know how much to ascribe his injuries and diminished production to his alleged performance-enhancing drug use — but it's hard to believe that there is no connection. If the Yankees knew what he was doing, then they ought to have realized that seven years was an awfully long time to hope the other shoe wouldn't drop. They were wrong.

9. Carlos LeeHouston Astros, six years, $100 million (2006)
The Astros may have seen Lee as sort of a low-grade version of Manny Ramirez, a big-time hitter who happened to be a brutal defender out in left field. But he doesn't possess Ramirez's tremendous command of the strike zone, and in recent years his on-base percentage has plummeted. Lee was decent enough during his first two years with the team, but he was much worse in 2009 and in 2010 he was one of the worst regular players in all of basebal. He still has two more years left on his contract, too.

Lee is the only man to ever sign for $100 million and receive fewer than seven years, which may indicate that the Astros thought he might not be worth such a long-term bet. But at this point in his career, he is virtually unplayable in the field, and his bat is no great shakes either. The Astros may have to hope they can convince another team to take him on as a DH and pay some of his salary. He isn't doing them any good by staying in Houston.

10. Alfonso SorianoChicago Cubs, eight years, $136 million (2006)
The Soriano contract is the position-player equivalent of the Barry Zito deal: hard to understand when it was signed, and simply awful now. At his absolute peak, Soriano was an exciting but deeply flawed player, possessing speed and power but indifferent defense and bad plate discipline. And the Cubs signed him for an inexplicable eight years following a career year when he was 30. Unfortunately, while speedy players are supposed to age well — as noted above — his defense and plate discipline actually appear to be eroding, and Soriano was one of the worst everyday players in the league in 2009. There are four more years on his contract. Unless he finally learns how to control the strike zone, the Cubs will regret each one of them.

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