5. Derrick Rose — 5 Years, $94 Million
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He was a hometown darling, a team leader and a superstar who averaged 25.0 points, 7.7 assists and 4.1 rebounds while taking his team to the conference finals as a 22-year-old.
You know how the rest goes.
Rose played just 39 games in the first year of his max extension, then tore his ACL in the opening round of the playoffs. That cost him all of the 2012-13 campaign and set off a cascade of injuries thereafter.
He logged only 10 games in 2013-14 and then managed 51 in 2014-15 while never coming close to his MVP form.
On balance, Rose has played below replacement level since his initial injury, as measured by box plus-minus and value over replacement player. Unavailability due to injury is the main reason this contract wound up looking so bad, but the fact that Rose was unproductive and inefficient when he was healthy enough to play made it worse.
After spending the final year of his deal with the Knicks in 2016-17, Rose is a free agent looking to prove he can help a winning team.