2. Brandon Roy — 5 Years, $82 Million
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The best defense of Portland’s five-year, $82 million extension for Brandon Roy, a player whose knees the team knew were questionable enough to warrant medical insurance as part of the deal, is that the former Rookie of the Year and two-time All-Star dramatically outproduced his salaries before signing it.

Roy had a fantastic 2009-10 season and earned All-NBA Second Team honors after averaging 21.5 points, 4.7 assists and 4.4 rebounds on 47.3 percent shooting. At the time, there may not have been a half-dozen more promising young talents in the league.

He earned $3.9 million in that banner season.

The extension kicked in during a 2010-11 campaign that saw Roy average only 12.2 points while missing 35 games. His knees were already shot.

Roy missed all of 2011-12 and retired at its conclusion.

The Blazers used the amnesty clause to remove his contract from the cap, and were in line to have insurance cover $17 million of the money still owed to Roy—so long as his injury resulted in “permanent disability.”

When Roy came out of retirement to play five games with the Minnesota Timberwolves in 2012-13, the Blazers had to pay the $17 million they thought they’d saved.

A five-year commitment for the max got Portland 35 sub-par games.

At least Roy delivered a memorable farewell.