MLB Free Agents 2014: A Look Back At The Highest Paid Free Agents Since 2004; Which Contracts Were Good, Which Contracts Were Bad?

With the 2014 Baseball Winter Meetings set to take place on Dec. 7 in San Diego, several teams will look to improve their chances to compete in the 2015 World Series by making a big splash with free-agent signings. While the intentions of general managers around the league might be good, recent history has proved that throwing money at the top available free agents isn’t always the most prudent move.

Max Scherzer leads a free-agent class that may see multiple players sign nine-figure contracts. The Detroit Tigers ace reportedly turned down a $144 million contract before the start of the 2014 season and went on to a 18-5 record with a 3.15 ERA. Jon Lester could get close to what Scherzer was offered, while James Shields and Hanley Ramirez may also seek deals in the neighborhood of $100 million.

If all four free agents stay healthy for the next few years and perform like they have in recent seasons, teams will be justified in paying them such large sums of money. The likelihood of that happening, however, doesn’t seem to be very good.

Only a small percentage of players who have received contracts worth at least $100 million have actually played to the level of their contracts. There are notable exceptions -- for example, Matt Holliday, who has made multiple All-Star game appearances and won a World Series, or Cliff Lee, who won the American League Cy Young award in 2008. The majority of those free agents, however, end up being vastly overpaid.

A look at the four highest paid free agents in each of the past 10 seasons does not bode well for the 2014-2015 free-agent class. While it’s undecided how well a few deals will be viewed when the contract comes to an end, 26 of the 40 deals players have not lived up to their lucrative contracts thus far.

The most expensive contracts fared the worst. Thirteen players who signed contracts of at least $100 million were overpaid, while only three have lived up to their deals. It’s too early to tell whether last year’s free agents Robinson Cano, Jacoby Ellsbury or Masahiro Tanaka will end up being worth what they are paid.

A few $100 million players can’t even be relied upon as everyday starters, with multiple years left on their contracts. Mark Teixeira has two years left on his eight-year deal, played just 138 games and hit .209 in 2013 and 2014. Meanwhile, one player whose deal concluded in 2013 with quite poor results was Barry Zito, who was paid $126 million from 2007-2013, never posted an ERA under .400 and finished his San Francisco Giants career with six losing seasons.

Even with multiple years left on their contracts, it’s fair to say that Carl Crawford, Josh Hamilton and Prince Fielder are vastly overpaid. Crawford, who signed with the Boston Red Sox and currently is on the Los Angeles Dodgers roster, looks like a shell of the player that he was with the Tampa Bay Rays, while Hamilton and Fielder have seen their power numbers plummet.

Some contracts were questionable from the start (e.g., Aaron Rowand’s five-year, $60 million deal with the San Francisco Giants). Some teams are prepared to sign a player in order to get immediate help, however, knowing he will likely be highly overpaid in the final years of his deal.

The Los Angeles Angels of Anaheim may have felt that way when they signed Albert Pujols to a 10-year deal worth $240 million. It would be unreasonable to expect Pujols to be an MVP candidate in the final years of the deal, when he will approach 40 years old, but the first baseman’s decline began in the first season of the deal. After 10 years of being one of the most dominant hitters baseball has ever seen, Pujols saw his on-base plus slugging percentage, OPS, dip below .900 for the first time in his career in all three seasons with the Angels.

Pujols, Hamilton and others who have underperformed during their mega-deals such as Alex Rodriguez and Alfonso Soriano all have one thing in common: They were signed after they turned 30 years old. General managers have fallen into the trap of signing players past their prime and expecting them to come close to repeating their past performance. Crawford signed when he was 28, but he entered the majors when he was just 20, perhaps logging enough work in those years that he became prone to injuries.

Seventeen of the contracts over the past decade (see list below) were to 30-year-olds who didn't play to their contracts, compared with five good contracts for 30-year-olds. Meanwhile, Scherzer, Lester, Shields and Ramirez are all 30 years old.

Below is a list of 40 players who were signed as the four highest paid off-season free agents each year of the past 10 years.

1. Alex Rodriguez, 32, 3B, New York Yankees, 10 years $275 million: Among the worst contracts ever, considering there is three years left and Rodriguez has totaled just 41 home runs since 2011. Verdict: Bad deal.
2. Albert Pujols, 31, 1B, Los Angeles Angels of Anaheim, 10 years $250 million: He hasn’t made an All-Star appearance since leaving St. Louis despite posting good numbers, though well below what he previously achieved. Verdict: Bad deal.
3. Robinson Cano, 31, 2B, Seattle Mariners, 10 years $240 million: Replicated his batting average and on-base percentage, OBP, from the previous year, though his slugging percentage dipped from .516 to .454. Verdict: Undecided.
4. Prince Fielder, 26, 1B, Detroit Tigers, nine years $214 million: Failed to hit more than 30 home runs in a season after doing so for five straight years and played just 42 games in 2014. Verdict: Bad deal.
5. Mark Teixeira, 28, 1B, New York Yankees, eight years $180 million: Hit at least 33 home runs with 108 RBI in each of his first three years, but hit .229, averaging 16 home runs and 53 RBI over the next three years. Verdict: Bad deal.
6. CC Sabathia, 28, P, New York Yankees, seven years $161 million: The team’s ace for four seasons, but he’s been a disaster since opting out and signing an extension, pitching just eight games in 2014. Verdict: Bad deal.
7. Masahiro Tanaka, 25, P, New York Yankees, seven years $155 million: A Cy Young candidate through two months, an injury limited him to 20 starts and could force him to have Tommy John surgery. Verdict: Undecided.
8. Jacoby Ellsbury, 30, OF, New York Yankees, seven years $153 million: Led the Yankees in steals and remained healthy for most of the season, but hit well below his career OBP at .328. Verdict: Undecided.
9. Zack Greinke, 29, P, Los Angeles Dodgers, six years $147 million: Registered two of his three lowest ERA’s with the Dodgers, winning 32 games in two seasons. Verdict: Good deal.
10. Carl Crawford, 28, OF, Boston Red Sox, seven years $142 million: Boston traded Crawford after a year and a half, and he hasn’t played more than 116 games in any of the past three seasons. Verdict: Bad deal.
11. Alfonso Soriano, 30, OF, Chicago Cubs, eight years $136 million: OPS never reached .900 in the entire contract. Stolen bases declined as soon as he joined Chicago. Verdict: Bad deal.
12. Shin-Soo Choo, 31, OF, Texas Rangers, seven years $130 million: Missed 39 games and hit just .242 with a .374 slugging percentage. Verdict: Bad deal.
13. Barry Zito, 28, P, San Francisco Giants, seven years $126 million: Went from one of the best pitchers in baseball to a back-of-the-order starter. Finished with an awful 63-80 record and a 4.62 ERA. Verdict: Bad deal.
14. Jayson Werth, 30, OF, Washington Nationals, seven years $126 million: Has a .303 average over the past three years, but he hit .232 in year No. 1 and missed half of the 2012 season. Verdict Bad deal.
15. Josh Hamilton, 30, OF, Los Angeles Angels of Anaheim, five years $123 million: Saw his home run total cut in half to 21 in year No. 1, and only played in 89 games in year No. 2. Verdict: Bad deal.
16. Cliff Lee, 31, P, Philadelphia Phillies, five years $120 million: Started just 13 games in 2014, but was an All-Star in 2011 and 2013.Verdict: Good deal.
17. Matt Holliday, 29, OF, St. Louis Cardinals, seven years $120 million: Consistently good on winning teams, Holliday has three All-Star appearances since signing this contract. Verdict: Good deal.
18. Carlos Beltran, 27, OF, New York Mets, seven years $119 million: Injuries hampered Beltran for stretches, but in 3,300 at-bats, he batted .282 with 202 homers -- good numbers but not worth the contract. Verdict: Bad deal.
19. Jose Reyes, 27, SS, Miami Marlins, six years $106 million: Hasn’t hit .300 since winning the batting title, averaging 28 steals, 79 runs and 132 games per season. Verdict: Bad deal.
20. Carlos Lee, 30, OF, Houston Astros, six years $100 million: First half of the contract went fine with a batting average well over .300 and 86 total homers, but it was poor numbers from there on out. Verdict: Bad deal.
21. Adrian Beltre, 32, 3B, Texas Rangers, six years $96 million: Consistently a top third baseman, averaging 29 home runs and 33 doubles per season. Verdict: Good deal.
22. Torii Hunter, 32, OF, Los Angeles Angels of Anaheim, five years $90 million: Consistent, with a .286 batting average, 21 home runs and 86 RBIs per season but not enough to warrant $18 million per year. Verdict: Bad deal.
23. Lance Berkman, 28, OF, Houston Astros, six years $85 million: Hit 45 homers in 2006 and led the league in doubles in 2008 and always had an excellent OBP. Verdict: Good deal.
24. A.J. Burnett, 31, P, New York Yankees, five years $82.5 million: His career was revitalized after a 2012 trade to Pittsburgh, but he had a 4.79 ERA with New York. Verdict: Bad deal.
25. John Lackey, 30, P, Boston Red Sox, five years $82.5 million: Only good for a stretch of 40 starts and missed the entire 2012 season. Verdict: Bad deal.
26. Anibal Sanchez, 28, P, Detroit Tigers, five years $80 million. Posted a 2.92 ERA in two seasons, but only started 50 games because of injuries. Verdict: Undecided.
27. C.J. Wilson, 31, P, Los Angeles Angels of Anaheim, five years $75.5 million: A 3.87 ERA in three seasons after having less than a 3.00 ERA in two of his three years prior to signing his contract. Verdict: Bad deal.
28. B.J. Upton, 28, OF, Atlanta Braves, five years $75.25 million: Has been one of the most unproductive players in the league, failing to bat over .208 in either season. Verdict: Bad deal.
29. Magglio Ordóñez, 31, OF, Detroit Tigers, five years $75 million: Solid player who had big seasons in three straight seasons, hitting 73 total homers. Verdict: Good deal.
30. Aramis Ramírez, 28, OF, Chicago Cubs, five years $75 million: Posted a slugging percentage above .500 in four of five seasons and earned a Silver Slugger award. Verdict: Good deal.
31. Jason Bay, 31, OF, New York Mets, four years $66 million: Only lasted three seasons in New York, averaging 96 games per season and never drove in more than 57 runs. Verdict: Bad deal.
32. Eric Chavez, 26, 3B, Oakland A’s, six years $66 million: Put up big power numbers and excellent defense in the first three years before tailing off. Verdict: Bad deal.
33. Derrek Lee, 30, 1B, Chicago Cubs five years $65 million: Only played 50 games in 2006, but hit 96 homers the next four seasons and won a Gold Glove. Verdict: Good deal.
34. Derek Lowe, 35, P, Atlanta Braves, four years $60 million: Never had an ERA less than 4.00 or pitched 200 innings over the length of the deal. Verdict: Bad deal.
35. Paul Konerko, 29, 1B, Chicago White Sox, five years $60 million: Elite power hitter posted excellent slugging percentage four out of five years. Verdict: Good deal.
36. Aaron Rowand, 30, OF, San Francisco Giants, five years $60 million: Never more than an average player, he was so bad in 2011 that the team released him with $12 million left on his contract. Verdict: Bad deal.
37. Jorge Posada, 36, C, New York Yankees, four years $52.4 million: A key part of New York’s 2009 World Series team, Posada hit just .242 with 101 RBI in the second half of the contract. Verdict: Bad deal.
38. Johnny Damon, 32, OF, New York Yankees, four years $52 million: Excellent OBP and stolen base totals along with good power numbers in four seasons. Verdict: Good deal.
39. Hideki Matsui, 31, OF, New York Yankees, four years $52 million: Injuries slowed this former iron man, though he posted solid power numbers when healthy in two seasons. Verdict: Bad deal.
40. Chone Figgins, 31, 3B, Seattle Mariners four years $36 million: Stolen bases and batting average plummeted after first year of contract. Verdict: Bad deal.

Here's a chart of the contracts: