16. Denílson de Oliveira Araújo

Year: 1998
Contract: 21.5 million
Team: Real Betis
When Real Betis made Denilson the highest-paid soccer player in the world, the last thing they expected was for their squad to go from the highest level of competition down to the Second Division (think going from the MLB to the minors). But that's exactly what happened only a year after signing the Brazilian World Cup winner. Even while playing at a lower-level, Denilson failed to produce for the team and was considered a liability before finally being sold to the French Club Girondins de Bordeaux in 2005. Even la joga bonito has it's share of ugly contracts.