Top 10 Worst Baseball Free Agent Signings over the Last 20 Years

Jim NeveauAnalyst IDecember 11, 2008

For baseball fans, the winter months are sometimes just as exciting as the actual season. Teams are constantly wheeling and dealing with a plethora of trades, free agent signings, and a general sense of drama hanging over the proceedings.

I’m sure I’m not alone in the feeling of elation that I get when my team scores a big name free agent. The anticipation of seeing what that player will bring to the club the following season is enough to send any baseball nut into a tizzy, and, as a fan of the Cubs, I’ve gotten to experience that feeling a lot in recent years.

This glee sometimes goes un-rewarded, however. For every player like a Manny Ramirez that can hit a city and make a huge impact, there are multitudes of guys who think they’re finding greener pastures elsewhere, and they end up scraping the bottom of the barrel a few years later.

With this in mind, here is my list of the top 10 worst baseball free agent signings in history.

10. Chan Ho Park, P5 years, $65 million from the Rangers in 2002

You would have thought that being the only pitcher to ever surrender two grand slams to the same player in the same inning would have been enough of an indicator that Chan Ho Park wasn’t all he was cracked up to be.

Well, to Rangers owner Tom Hicks this wasn’t enough proof.

A man who is becoming famous for overpaying players and then whining about it later, Hicks signed Park to one of the most lucrative contracts for a pitcher in history, showing him the rewards for having a 15-11 campaign in 2001 with the Dodgers.

Park did little to earn this contract after receiving it, pitching to an abysmal 10-11 record in his first two seasons in Texas, with an ERA well above 6.00. He was frequently hampered by injuries, and eventually the Rangers traded him in 2005 to the San Diego Padres.

He is still trying to make a comeback into baseball, but injuries still haunt him to this day.


9. Albert Belle, LF5 years, $65 million from the Orioles in 1999

Albert Belle will always be viewed by most baseball minds as one of the most hated players in the history of the game. He had a nasty temper, illustrated nicely by stories of destroying thermostats and boom boxes with his trusty corked bat at his side.

In the winter of 1996, Belle signed with the White Sox for a five year deal worth $55 million. This contract had a stipulation that Belle could opt of the contract and automatically receive a top-three salary in the league, and he took advantage of this in the winter of 1998.

After the Sox declined re-signing him, the Orioles were the lucky victims of fate, agreeing to a huge contract with the slugger. He managed to play just two more seasons, until he had to retire with a hip condition.

This contract would have been higher on the list, but the Orioles got a good chunk of the money from the contract back due to an insurance policy they had inserted into the contract. Lucky them.

8. Juan Pierre, LF5 years, $44 million from the Dodgers in 2007

Juan Pierre is still one of the best singles hitters in the game of baseball today, but unfortunately for him and the Dodgers, that is all he is.

Pierre signed his deal after a halfway decent season with the Cubs. In that year, he had an average of .292 and collected 204 hits. He also stole 58 bases.

In the first year of his contract, he hit .293 for the season, while also stealing 64 bases. This apparently wasn’t good enough for the Dodgers, as they brought in Andruw Jones (an honorable mention on this list) to replace Pierre in center field. He was eventually shifted over to left field and lost his starting job about midway through last season.

Looking at his numbers, his RBIs have slowly decreased since 2004, and his walk totals have followed suit. Clearly the Dodgers don’t value his services very highly, and they are stuck paying him nearly $9 million a season for the next three years to sit on their bench.

7. Carl Pavano, P4 years, $39.95 million from the Yankees in 2005

This may not be one of the biggest contracts ever signed by a free agent, but the lack of earning that Pavano did for the contract is staggering.

After a 18-8 record with the Marlins in 2004, the Yankees decided that they needed some new blood on the pitching staff. When they brought Pavano into the fold, things started going wrong almost immediately.

In June of 2005, Pavano injured his shoulder and was placed on the DL. He missed the rest of that season, and then all of 2006 with various injuries.

Pavano managed to pitch three games in 2007 before going down with an elbow strain that eventually resulted in him having Tommy John surgery. In 2008, he managed a 4-2 record with a 5.77 ERA and gave up 23 runs in his seven starts.

Pavano is currently rehabbing in Tampa, FL, waiting for a team to call upon the man whose agent still insists that he is still ready to be a 1-2 starter and go 200+ innings in a season.

6. Jason Giambi 1B/DH7 years, $120 million from the Yankees in 2002

You know, I’m betting that the Yankees weren’t thinking about steroids and facial hair when they signed Jason Giambi to this enormous contract in 2002.

Before he donned the Bronx Bombers uniform, he had a fantastic couple of seasons with Oakland, hitting 124 home runs and 280 RBI in his final three seasons in the Bay Area. He also played at least 150 games for four consecutive seasons at the end of his run in green and gold.

After he signed his contract, he managed to have two good seasons in a row for the Yankees, hitting 41 homers in each campaign, but the Yankees still couldn’t win that elusive title. In 2004, everything began to fall apart.

He only played 80 games in that season, hitting .208 with 12 home runs. He also was implicated in the notorious “Game of Shadows” in 2006, in which leaked grand jury testimony implicated Barry Bonds and Giambi in the BALCO scandal.

To Giambi’s credit, he apologized for using steroids in May 2007, and he cooperated with the Mitchell Report as well.

In 2006, he had a bit of a resurgence with 37 home runs and 113 RBI, but he batted .253 and only managed 113 hits over the course of his 139 games. In 2007, he backslid a bit, only playing in 83 games and hitting a horrendous .236 with 14 home runs and 39 RBI.

Injuries and steroid abuse conspired to knock Giambi from the upper echelons of the Major League hierarchy, and earned him this spot on this list.


5. Denny Neagle, P5 years, $51 million from the Rockies in 2001

After going 15-9 with the Cincinnati Reds and New York Yankees in 2000, Denny Neagle signed a lucrative deal with the Colorado Rockies that made him one of the wealthiest pitchers in the game. Mr. Neagle quickly proved, however, that he was not worth the money.

Over the course of the next two seasons, Denny compiled a gaudy record of 17-19, with an ERA above five, gave up 55 home runs, and hit 17 batters. In an injury shortened 2003 season, he also went 2-4 with an ERA of 7.90.

Unfortunately for Denny, his troubles didn’t end there.

He missed all of the 2004 season with elbow ligament surgeries, and he was released by the Colorado Rockies after he found himself embroiled in legal trouble. After he was arrested with a hooker and driving under the influence, he was released by the team and sent on his way.

In 2005, he signed on with the Devil Rays, but once again was unable to play due to recurring injuries. After several other arrests and legal troubles, Neagle’s career ended in a sea of criminal activity and unrealized potential.

4. Barry Zito, P7 years, $126 million from the Giants in 2007

If anyone personifies being overblown on the free agent market, it’s Mr. Zito. He came in to the Giants organization making a name for himself for the team across the Bay (the A’s), with his guitar playing antics and his ridiculous curve ball.

He threw at least 200 innings in each of his six full seasons with the Athletics, and he was a three-time All-Star. He also won the Cy Young Award in 2002 with a 23-5 record, and he struck out 205 batters in 2001. He also never missed a scheduled start. It was for all of these reasons that the Giants committed the biggest contract ever given to a pitcher to let him pitch in friendly AT&T Park.

The park and team have been anything but friendly to him.

In his two seasons in Rice-a-Roniville, Zito has a 21-30 record, with an ERA near 5.00 and 40 home runs given up. He also set a career high by allowing 102 walks in 2008.

Things got so bad for him last season that he was demoted from the starting rotation for part of the season, as youngsters Matt Cain and Tim Lincecum showed dominance and a reason for hope in San Fran.


3. Mo Vaughn, 1B6 years, $80 million with Angels in 1999

Mo Vaughn came to the Angels after a checkered final season with the Boston Red Sox. He got into an altercation at a nightclub when he punched a man, and he crashed his truck on his way home from a strip-club. His off-field troubles didn’t affect his on-field track record, as he combined to slug 75 home runs with teammate Nomar Garciaparra.

When he came cross-country and suited up for the Halos, he was productive—when he was healthy. He hit 30-plus home runs in his first two seasons in Anaheim, but he caught a nasty case of the injury bug when he came to California.

In fact, before his first game, he fell down the dugout steps on his first play as an Angel and badly sprained his ankle. It was these kind of nagging injuries that led to him missing the entire 2001 season and he was subsequently traded to the Mets after the season.

When Troy Percival said that the Angels wouldn’t miss Vaughn’s leadership, Mo taunted his former team, saying that they had “no flags hanging at friggin’ Edison Field, so the hell with them”. It must have felt pretty good for Troy and the Angels to win the World Series the first season after Mo took his act to New York.

He played limited ball in 2002 and 2003, ballooned to 275 pounds, and was sidelined permanently by a knee injury that last season. The trade that netted the Mets Vaughn was orchestrated by Steve Phillips, who is casually referred to as “the GM” on ESPN. I wish my legacy was that I pulled off one of the worst trades in history and get a cushy job at ESPN.


2. Kevin Brown, P7 years, $105 million in 1998 from the Dodgers

Quick! Tell me what you do with a 33 year old pitcher who had an 18-7 record for a team that made the World Series?

If you answered give him the first $100 million contract in Major League history, then you must be the GM of the Dodgers who decided to give exactly such a deal to Kevin Brown, who proceeded to win an average of nine games a season for the rest of his career.

After finishing third in Cy Young voting, Brown wanted to pay closer to his home in Georgia, but what kind of moron would turn down that kind of coin?

In his first season, he posted an 18-9 record with an even 3.00 ERA, which is obviously respectable. After this, however, his performance began to slowly suffer as he caught the injury bug, missing significant time between 2000 and 2002. In 2003, he had a resurgence of sorts, going 14-9.

This number, however, is undermined, as Brown was one of the players suspected of steroid abuse in the Mitchell Report. Kirk Radomski claims he sold Brown HGH between 2000 and 2001.

In 2003, he was traded to the New York Yankees, and  his most notable accomplishment in the Bronx was breaking his hand after arguing with Joe Torre. He tried one more comeback attempt in 2005, going 4-7 with an ERA of 6.50.

1. Mike Hampton, P8 years, $121 million in 2001 from Rockies

If Denny Neagle and Mike Hampton have taught Major League pitchers anything, it is this: when Colorado comes calling with huge contracts, RUN AWAY! Coors Field is apparently where good pitchers go to die, and Hampton was not an exception to this rule.

In his first season in Colorado, he went 14-13 with an ERA of 5.12, and in his next season, he was even worse, going 7-15 with an ERA of 6.15.

After these two horrendous years, he was traded to the Florida Marlins, and then to the Atlanta Braves.

In 2003, he won 14 games, and in 2004, he won 10 of his final 11 starts, but in 2005, the wheels came off again. He managed 12 starts before being lost for the season, and then had Tommy John surgery, costing him his entire 2006 season.

In 2007, he was expected to rejoin the rotation, but after an oblique injury, it was again revealed he had recurring elbow pain, and had another reconstructive procedure, costing him the entire season.

In 2008, he actually managed to make a couple of starts, going 3-4 with a 4.85 ERA, giving up 10 home runs in 13 starts, and walked 28 batters in 78 innings.

He currently has a contract with the Houston Astros, and is still wanting to try to make a name for himself as a quality middle of the rotation pitcher.


Well, there you have it: my list of the 10 worst baseball free agent signings ever! Will Francisco Rodriguez or CC Sabathia make their way on here? We will have to wait and see.


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