Worst free agent signing in Portland Trail Blazers history: Darius Miles
6 Years, $48 million
The prep-to-pro generation of the NBA produced a number of interesting storylines, from stars such as Kevin Garnett and Kobe Bryant to disappointments such as Kwame Brown or Eddy Curry. One of its most interesting and at times polarizing was Darius Miles.
The 6-foot-9 forward was drafted third overall by the Los Angeles Clippers, coming straight out of high school in Illinois. He was a part of a fan favorite group of high-flying athletes on the Clippers, including Quentin Richardson and Corey Maggette. Although he did not make the playoffs with the Clippers, they did increase their win totals each year.
After a season-and-a-half with the Cleveland Cavaliers, he was traded to the Portland Trail Blazers, after which he signed a six-year, $48 million contract with Portland.
In January 2005, just months after signing his new contract, he got into an altercation with head coach Maurice Cheeks that turned violent and racial. Miles was suspended for two games, and the locker room was not the same after that.
The following season, Miles went down with a knee injury late in the year, an injury that required microfracture surgery. He missed the next two seasons with the injury, cratering his career.
The Trail Blazers petitioned the NBA to declare Miles’ injury career-ending to recoup some salary cap savings, but gamesmanship by the Memphis Grizzlies in 2008-09 prevented those savings.
In the end the Trail Blazers’ investment in Miles resulted in just 103 games, an extended headache getting his money cleared and one of the league’s modern black-spots in terms of player conduct.