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

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, P—5 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, LF—5 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, LF—5 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, P—4 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/DH—7 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.

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