Houston Rockets Nene ordeal: 4 times the NBA voided deals

Chris Dudley’s 1993 and 1994 Contracts with the Portland Trailblazers
In 1993, defensive ace Chris Dudley agreed to a seven year contract worth $11 million with the Portland Trail Blazers. The contract included a “player option” after the first season with the Blazers, which was actually the first deal to ever include the player option in league history.
Interestingly enough, Dudley actually suffered an injury during the first year of his deal with Portland, limiting him to just six games during the 1994 season. At the time the contract was inked, then commissioner David Stern voided Dudley’s contract, as he claimed the one year “player option” was an attempt to circumvent the salary cap. This eventually made it’s way to NBA “special master” Merrell Clark, who ruled in favor of Dudley.
At the conclusion of that season, Dudley actually exercised his player option and agreed to terms with Portland on a new six year deal worth $24 million. The league voided the deal again, as they determined the contract violated the salary cap, because it allowed him to circumvent its cap rules. After losing the first time, Stern and the league were surely going to challenge Dudley again. The league took this battle to the federal courts and were ultimately defeated, as judge Dickinson Debevoise denied the league’s claim once again, ruling in favor of Dudley.
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