Top 10 Worst Contracts in History

Bobby Bonilla

Sometimes a big contract doesn't mean a big return. We look at some of the worst contracts in sports history!

#10. Worst Contracts - Grant Hill

This pick should not be blamed too heavily on the Orlando Magic who signed Grant Hill to a seven-year, $93 million contract. At the time Hill was one of the best players in the league, but injuries plagued his career in Orlando and he only played in 47 games in his first four seasons! He never regained his superstar status.

#9. Worst Contracts - Ryan Leaf

Ryan Leaf may be the biggest bust in NFL history. The Indianapolis Colts almost picked Leaf over current superstar Peyton Manning with the first overall pick in the 1998 Draft. Instead the San Diego Chargers chose him with the second pick, and signed him to a four-year, $32.5 million contract. Leaf lasted only four unproductive seasons, while Manning became the best quarterback in the game.

#8. Worst Contracts - Pavel Bure

When the Florida Panthers signed Russian sensation Pavel Bure to a five-year, $47.5 million contract in 1999, they thought they had the next Wayne Gretzky. Unfortunately they were wrong. They were forced to trade Bure to the New York Rangers in 2002.

#7. Worst Contracts - Rick Pitino

In 1997, the Boston Celtics signed Rick Pitino to a seven-year, $70 million contract, but Pitino wasn't a player - he was the coach. The legendary University of Kentucky coach was brought to bring the Celtics back to glory. The exact opposite happened, as the Celtics failed to make the playoffs in his four-year tenure. He was canned in 2001.

#6. Worst Contracts - Bobby Bonilla

In 1992, the New York Mets signed Bonilla to a huge five-year, $25 million contract. It was one of the most lucrative baseball contracts at the time. His stats dropped significantly after the contract, and the Mets ended up trading him just three years later.

#5. Worst Contracts - Akili Smith

After long negotiations, the Cincinnati Bengals were finally able to sign their 1999 top draft pick Akili Smith to a seven-year, $56 million contract. He never fit in the Bengals' offense and ended up being cut in 2002.

#4. Worst Contracts - Alex Rodriguez

To justify a 10-year, $252 million contract in baseball, you have to win lots of World Series titles. For Alex Rodriguez, he has failed to do that ever since the Rangers gave him this ridiculous contract in 2000. Don't get us wrong: A-Rod is good, but for that cash you have to be great.

#3. Worst Contracts - Juwan Howard

In 1996, the Washington Bullets gave Juwan Howard the biggest contract in NBA history at the time with a seven-year, $105 million contract. Although he ended up being a solid player, he never went to another all-star game after signing the contract.

#2. Worst Contracts - David Beckham

Sure his name will sell tickets, but is giving David Beckham - a 32-year old past-his-prime soccer player - a five-year, $250 million contract a good idea? We will see if the $50 million a year gimmick is worth the investment.

#1. Worst Contracts- Jerome James

Following the 2004-05 season, the New York Knicks foolishly gave Jerome James a five-year, $30 million contract. Although this amount seems small compared to the other contracts above, this money was given to a player who has no business of even playing in the NBA. Talk about him hitting the jackpot here!

Related Stories:

Top 10 Cool Sports Names

Top 10 Worst Sports Haircuts

Top Five Worst Sports Movies

More Cool Sports Trivia!