MLB Free Agency: 50 Biggest Free-Agent Busts of All Time
Dan Tylicki@DanTylickiAnalyst IDecember 28, 2010MLB Free Agency: 50 Biggest Free-Agent Busts of All Time

The baseball offseason is characterized by the free agency movement, where players sign with teams for top dollar. It seems as if every year, another free agent breaks the record for biggest contract. When these major deals in particular don't work out, then they hurt the organization big time.
It seems to happen all too often; a player is signed to a major contract only to fail miserably, whether it's due to injury or ineffectiveness. Even as early as last year, we could find contracts that did not work out, and now that salaries have exploded, this will continue to happen. As for these 50 free agent busts, they're just happy that, for most of them, they're past this experience.
50. Andy Messersmith, Atlanta Braves

This Dodgers pitcher was one of the original free agents that helped to get the ball rolling on the market, and signed with the Atlanta Braves to a three-year, $1 million deal, big in 1977.
After coming off two Cy Young-caliber seasons, winning 20 and 19 games in two years, he went 11-11 in his first year with the Braves. After a worse second season, the Braves were able to get rid of the last year of his deal when the Yankees purchased him, where he played in six games.
49. Dave Collins, New York Yankees

Collins had a decent career and was a nice role player that the Yankees wanted. As a result, they signed him to $650,000 a year in 1982, star money, despite only playing a full season once. He had an okay year, but the Yankees realized their mistake and quickly traded him away in a package that included a young Fred McGriff.
48. Roger Clemens, New York Yankees

Normally I would not consider the stretch of a 44 year old to be a bust, but with the money the Yankees paid him, it has to be included. After coming over a good spot year with Houston, He signed a one-year deal worth $28,000,022. He pitched .500 ball in 18 starts and faltered in the playoffs.
47. Matt Young, Boston Red Sox

Another early 90s Red Sox move I can't figure out. He spent the 1990 season with the Mariners, where he went 8-18. The Red Sox felt that he just had a hard luck season, and signed him to a contract worth over $2 million a year. He started 24 games in two years and won only three games. He's not higher because his expectations could not have been that great.
46. Carlos Beltran, New York Mets

The Mets get a lot of flack for this deal, when it really wasn't all that bad. He's made four All-Star appearances as a Met, and after struggling out of the gate, his next few seasons were really good. Unfortunately, he has only played the half the season in 2009 and 2010, and the contract has went from good enough to bust potential.
45. Juan Pierre, Los Angeles Dodgers

This one may not be Pierre's fault. After a great year with the Cubs, he was available for any team that needed a dependable leadoff hitter. The Dodgers signed him to a three-year deal, making $10 million his final year. His first season went as expected, then the Dodgers brought in two players that forced Pierre to the bench.
Who were those two players? Well, both happen to be coming up later in the rankings.
44. Storm Davis, Kansas City Royals

The Royals decided to jump into the free agent market in 1990, and signed Storm Davis to a seven-figure per year deal after a 19-win season at Oakland. He went 7-10 his first season, then was relegated to bullpen duty the following year. The Royals ended up trading him to Baltimore to get rid of a deal that never came close to working out.
43. Manny Ramirez, Los Angeles Dodgers

Manny Ramirez had many great years in Boston, and in 2008, he was traded to the Dodgers. In 53 games he hit nearly .400. As a result, the Dodgers signed him to an immense two-year deal worth over $40 million. He played well in between a 50-game suspension and injury, but he was far from what the Dodgers paid for.
The first of the duo to relegate Juan Pierre to the bench.
42. Aramis Ramirez, Chicago Cubs

Much like Carlos Beltran, he was signed to a huge, multi-year deal and started off well, but has had problems the last two years. He still has a couple years left on the deal to get himself off this list, though it looks unlikely.
41. Greg Vaughn, Tampa Bay Devil Rays

Vaughn seemed to come out of nowhere and have great 1998 and 1999 seasons. As a result, the Tampa Bay Rays signed him to a big three-year deal worth almost $25 million. He responded with two okay seasons and one awful one, hitting .163 in 69 games.
40. Kevin Brown, Los Angeles Dodgers

I don't think this one is that awful, but he appears on most bust lists, so he's included. He finished an 18-game winning season with the Padres, and signed with the Dodgers for $100 million.
Brown actually had four very good years with the Dodgers, though one was injury-riddled. He kept an ERA of 3.00 or lower in all four seasons at the height of the steroid era, and made a couple All-Star appearances in the process.
The Dodgers overpaid, but he played as well as he played anywhere in his career, so if he's a bust, that's the Dodgers' fault.
39. Richie Sexson, Seattle Mariners

Richie Sexson had a few very good years in Milwaukee, but struggled in Arizona in 2004. Despite this, the Seattle Mariners signed him to a $50 million deal over four years. He had two years of 35+ doubles and HR and 100+ RBI, and seemed to perform as advertised.
In the final two years of his deal, he stopped hitting, could barely break .200 and finished both years with negative WAR. He performed no better with the Yankees, where he ended his career.
38. George Foster, New York Mets

The second of three guys signed for power but failed to produce, George Foster was a beast during his time on the Reds. In 1982, he signed with the Mets for five years, making nearly $3 million his final year. His average was no longer good, and he still had some power, but he was a shell of his former self and not worth what the Mets paid.
37. Jason Giambi, New York Yankees

Giambi was coming off two amazing seasons with Oakland, so naturally the Yankees threw him as much money as they could, over $20 million a year for his final three years. His power remained mostly intact, but his batting average went from .308 in Oakland to .260 in New York, aside from missing a large part of two seasons.
I'm not sure how he's still in the league.
36. Adrian Beltre, Seattle Mariners

There's a reason Beltre is not getting signed to the amount he may want. After an amazing season for the Dodgers in 2004, he signed a big contract with the Seattle Mariners. In five seasons, he played decently and won a couple Gold Gloves, but was not a star.
In 2010 with the Boston Red Sox, he had an amazing year again, which ironically just makes him look worse, as it made him seem like he only plays well in contract years.
35. Steve Kemp, New York Yankees

Yet another player who had some power in the 80s, the Yankees signed him to a multi-year deal in 1983 for five years and $5.45 million.
He was worth perhaps a fourth of that after playing just over half the season in the two years he played for the Yankees. He was shipped to Pittsburgh after the 1984 season, and was even worse there.
34. Ken Griffey, Jr., Cincinnati Reds

When the Reds signed him to a contract after the 1999 season, he was THE free agent, and in his prime, was on pace to be one of the best players of all time.
In Cincinnati, he was very good when healthy, but unfortunately, he just wasn't all that healthy. The expectations going into Cincinnati compared with the end result may label him as a bust, though he's still a first-ballot Hall of Famer when the time comes.
33. Ed Whtison, New York Yankees

Another player who had problems with the Yankees for some reason. After a solid season with San Diego, he signed with the Yankees for the 1985 and 1986 seasons.
Whitson pitched okay in 1985, but struggled badly the year after that, finishing his Yankees tenure with an ERA of 5.36. He had several good years with San Diego after rejoining them, making him look decent in the end.
Some people just should not pitch for the Yankees.
32. Danny Tartabull, New York Yankees

In 1991, Tartabull had a career year with the Royals, hitting .316 with 31 home runs. The Yankees needed some power and signed him to a deal worth over $5 million a year. He provided good power for a couple years, then struggled and was sent to Oakland. Not the worst move by the Yankees, but they were hoping for a lot more from him.
31. Alfonso Soriano, Chicago Cubs

You know what the worst part of this deal is? He still has four years left, so this contract still has the possibility to become a true stinker. He could still rebound too, but that seems unlikely now.
30. Matt Morris, San Francisco Giants

Matt Morris was a big piece of the Cardinals rotation, and they seemed to let him go just in time. He signed with the San Francisco Giants to a big three-year deal, and went 10-15 his first year, 7-7 his second and was traded to the Pirates where he ended his career.
29. Julio Lugo, Boston Red Sox

After Lugo struggled with the Dodgers when he was traded to them in 2006, the Boston Red Sox decided to take a chance on him, and gave him a contract worth nearly $10 million a year. He only played one full season with the team, and hit .237 in it. His best WAR as a Red Sox player? 0.4.
28. Mark Davis, Kansas City Royals

When you acquire a Cy Young winner through free agency, you expect him to be good. For the Royals and Mark Davis, that didn't work out. He signed a deal worth over $3 million a year, and in three seasons with the Royals, he went 9-13 with a 5.31 ERA.
27. Danny Jackson, St. Louis Cardinals

The Cardinals usually do a great job on selecting the right starting pitchers, but even they mess up. In 1995, the Cardinals signed Jackson to a three-year deal worth around $10 million. He went from a 14-6 record in 1994 with the Phillies to a 2-12 record and a 5.90 ERA, and never got any better for the Cardinals.
Unlike others on the list who retreated to the Padres after the bust, he couldn't even pitch in San Diego after being traded there.
26. Kevin Millwood, Texas Rangers

In 2005, Millwood had the definition of a hard luck season with the Indians. He had a record under .500, yet led the league with an ERA of 2.86. As a result, the Texas Rangers signed him to a four-year contract worth about $48 million. He was a starter all four years, which is better than we can say about some, but his ERA was over 5.00 in two seasons, and he was nowhere near the ace the Rangers were hoping for.
25. Nick Esasky, Atlanta Braves

This one was the victim of bad luck, rather than the team making a bad call of the player suddenly sucking. After having a career year with the Red Sox in 1989, Esasky signed with the Atlanta Braves and signed for three years in a deal worth nearly $6 million. He played only nine games for the Braves, as vertigo ended his career early.
He spent some time in the minors in 1992 to try to make a comeback, but it didn't work out.
24. Russ Ortiz, Arizona Diamondbacks

Ortiz had two very good years with the Atlanta Braves when the Diamondbacks signed him to a four-year deal. However, he pitched so badly that he was cut a year-and-a-half into it. He went 5-16 with an ERA of 7.00 as a member of the D'backs.
23. Barry Zito, San Francisco Giants

Zito finally seems to be pitching okay with the Giants, having turned into a solid number four or five option. The problem with that is that he was meant to be an ace, and is paid as such. He's being paid over $18 million a year to pitch .500 baseball with an ERA around four. He has time to rebound and pitch well again, but that time is running out fast.
22. Mo Vaughn, California Angels

The big man on campus was one of the big power hitters of the 90s, and as a result, the Angels signed him from the Boston Red Sox to a six-year, $80 million contract. He started off well with the Angels, having two great power seasons before disappearing for a year
It was Mo Vaughn's three-year deal with the Mets however, which was worth nearly $50 million, that sealed this as a bust. After missing the 2001 season while with California, he was nowhere near the hitter he was while he was with the Mets.
21. Gary Matthews, Jr., Los Angeles Angels Of Anaheim

I'm still not sure what compelled the Angels to make this move. Nonetheless, in 2006, Gary Matthews finally had a very good year with the Texas Rangers, hitting .313 in 147 games, both career highs.
The Angels signed him to a five-year, $50 million deal, and he played a full year in 2007, then was put on bench duty after that. He was shipped to the Mets for the 2010 season.
The worst part? He may not play in the majors next year and the Angels still have a year left to pay him.
20. Danys Baez, Baltimore Orioles

When he was a rising prospect in Cleveland, I didn't feel the hype at all. I still don't get what the draw was. After he had an average year in relief in 2006, the Baltimore Orioles signed him to a three-year, $19 million deal. His statline was 4-12 with a 5.02 ERA while not playing in the majors in the middle year.
He now plays for the Phillies, where he's...actually still very mediocre. At least his $2.75 million salary is somewhat more realistic than Baltimore's.
19. Aaron Rowand, San Francisco Giants

Everyone was iffy about Jayson Werth's contract after coming out of nowhere to have a great year in a rare full season for him. Exhibit A on why he could become a bust is Aaron Rowand. In 2007, he had his second great year, hitting .309 and winning a Gold Glove, and as a result the Giants signed him to a five-year, $60 million contract.
The output? Two decent seasons, and he's now riding the bench for the Giants as they try to pay off the rest of the contract. In 2010, he hit .230 and only seems to be getting worse.
18. Juan Gonzalez, Texas Rangers

Juan Gonzalez was showing signs of slowing down when he signed with the Indians in 2001. He had a comeback year, hitting .325 and finishing fifth in MVP voting. As a result, Texas wanted him back and they signed him for two years with a contract worth $24 million. He played 152 combined games, and while he hit well enough while active, it was a waste of money for a guy on the downswing.
17. Steve Karsay, New York Yankees

Another one on the "good when active list," the Yankees signed Karsay to a four-year, $22.5 million contract. For starters, they signed a reliever for that much. He actually had a good first year in 2002, going 6-4 with a 3.26 ERA. However, he missed the next season due to shoulder surgery, and never really regained his form on the diamond.
16. Derek Bell, Pittsburgh Pirates

After having a decent season for the Mets in 2000, Bell was signed by the Pittsburgh Pirates for $5 million. He hit .173 and flat out stunk for the Pirates, and then came Operation Shutdown. That's something to look up for yourself (just because it's hard to believe), but essentially the Pirates paid him in 2002 to not play for the team and to go home.
15. Bobby Bonilla, New York Mets

Maybe Bell was revenge for this. After having two amazing years with the Pirates, Bonilla signed with the Mets before the 1992 season for five years and $29 million. His production was decent, but it wasn't even close to what he was pulling off in Pittsburgh, and they sent him to Baltimore in 1995.
His second contract with the Mets is quite likely the worst one in history, as the Mets are paying it off indefinitely.
14. Milton Bradley, Chicago Cubs

I'm not sure which move is worse, the Cubs offering this contract, or the Mariners trading for it. Probably the latter. The Cubs offered him a three-year, $30 million deal after having a very good season with the Rangers. Bradley struggled with the Cubs, and his time with the Mariners so far...well, saying it's been bad doesn't really do it justice.
13. Vince Coleman, New York Mets

Coleman was one of the baserunning showstoppers of the 1980s, running wild for the Cardinals. Once he signed a three-year deal with the Mets though, suddenly that was it. He stats took a nosedive, he never played a full season and his off-the-field antics were infamous. When you spend much of your salary on Bonilla and Coleman, of course the team's not going to work.
12. Darren Dreifort, Los Angeles Dodgers

When you allow a player to enter free agency and you end up re-signing him, how could it go wrong? In the case of Darren Dreifort, it can go very wrong. He was signed to a five-year, $55 million deal, Injuries took their toll, as he was sidelined most of the time. His statline during the contract was 9-15, a 4.64 ERA and just over 200 innings pitched.
11. Chan Ho Park, Texas Rangers

The Rangers seem to have no luck with pitching. After a solid 2001 season with the Dodgers, the Rangers signed Park to a five-year, $65 million contract. He pitched badly for three-and-a-half seasons, and he was eventually traded to where every pitcher goes when they want to revive their career, the Padres.
10. Kei Igawa, New York Yankees

Perhaps the worst of the Yankees' signings. It wasn't for all that much money, $20 million over five years. However, he's made 13 career starts and gotten two wins as he languishes in the minor leagues. Just because the Red Sox got Dice-K, the Yankees felt obligated to get Igawa.
But was he the biggest free agent bust for the Yankees? No. We all know what is...
9. Carl Pavano, New York Yankees

If you mention his name to a Yankees fan, an instant stomach ache ensues. After Pavano's career year for the 2003 Florida Marlins, the Yankees signed him to a $40 million contract for four years. Injuries relegated him to 26 starts and nine wins.
In 2010, we see the exact same situation, though the Yankees are not going to go near him, whether they need pitching or not.
8. Darryl Strawberry, Los Angeles Dodgers

For as much as one would expect the Yankees to have many top-10 picks here, Pavano wraps up the list for them. The Dodgers, on the other hand, have three in the top eight.
The first, and perhaps the most well-known of the three, is Mets phenom Darryl Strawberry. He made seven straight All-Star appearances for the Mets, and the Dodgers signed him to a five-year, $22.25 million contract.
He played well his first season, but after that he played 43 and 32 games in two straight seasons, respectively, and the Dodgers cut their losses and released him.
7. Bruce Sutter, Atlanta Braves

It seemed like a good idea at the time to acquire the only current Hall of Famer on the list. Bruce Sutter was one of the best relievers in the game for the Cubs and Cardinals. The Atlanta Braves signed him to a six year, $10 million contract. They ended up with a pitcher who pitched 112 games but had an ERA over 4.50. He pitched in 1985 and 1986, was hurt for the entirety of 1987 and retired at the end of the 1988 season.
6. Andruw Jones, Los Angeles Dodgers

Jones was coming off a 2007 season in which he hit .222 and was showing clear signs of slowing down. So, what do the Dodgers do? Sign him to a two-year deal worth $36.2 million. They got a .158 average in 75 games for their troubles. Not 33, I can't see Jones remaining in the game much longer.
5. Denny Neagle, Colorado Rockies

In a move that the Rockies had absolutely no business making, they signed Neagle to a $51 million, five-year contract. He had just come off a Yankees stint with a .500 record and 5.81 ERA, and fared no better with the Rockies. He lasted half of his deal, and finished his time in Colorado with a 19-23 record and 5.57 ERA.
4. Albert Belle, Baltimore Orioles

Maybe this is a bit high, but no one likes Albert Belle, so I don't have to worry. After very productive but difficult years with the Indians and White Sox, the Baltimore Orioles signed Belle to a five-year, $65 million contract. He had two fairly productive seasons, then...nothing. The Orioles shut him down and he retired due to hip issues. Belle is not the kind of player to sign to a long-term deal.
3. Jason Schmidt, Los Angeles Dodgers

Why, Dodgers? Nothing seems to work for them, as evidenced here. Signing a guy to a three-year, $47 million contract sounds nice when he's pitching fairly well, as Schmidt was.
However, when the free agent ends up pitching 10 games and winning three, suddenly that's an all-time bust. That's over $15 million per win, nearly $5 million per appearance for Schmidt.
2. Wayne Garland, Cleveland Indians

The original free agent bust. Garland won 20 games in 1976, and was the big target in the first year of free agency. The Cleveland Indians signed him to a 10-year, $2.3 million deal. All for, until 1976, an unproven pitcher.
He had an okay first year, but led the league in losses. Why was he struggling? He tore his rotator cuff in spring training, and his next four years were all disasters. He retired after the 1981 season, finishing only half his contract.
1. Mike Hampton, Colroado Rockies

Mike Hampton is the epitome of the free agent bust, so much so that multiple teams have felt the effects of a single bad contract. Hampton had an outstanding year with the Astros in 1999, and a very good year with the Mets in 2000. When he entered free agency, the Colorado Rockies jumped at the opportunity and offered him an eight-year deal worth $121 million.
Hampton pitched poorly in two seasons with Colorado, and he was traded to the Florida Marlins. The Marlins immediately traded him to the Atlanta Braves without letting him pitch a game. He had a couple decent seasons for Atlanta, and then struggled in 2005 before missing 2006 and 2007. After one more lackluster year in 2008, all involved rejoiced at the conclusion of his contract.