Like the very fabric of Wesley Matthews‘ Achilles tendon, the Portland Trail Blazers‘ season — and ultimately, their long-term future — was ruptured in an instant. When Rip City’s favorite 3-and-D weapon went down with a torn left Achilles on Mar. 5, 2015, the injury not only doomed Portland’s faint hopes of contending for a title, but its current core as well.

It was only about a year ago that LaMarcus Aldridge was saying he wanted to be the greatest Portland Trail Blazer ever. Now, he’s preparing to suit up alongside Tim Duncan and the San Antonio Spurs, and his imminent departure is what prompted a summer of total restructuring to rebuild around Damian Lillard.

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With four of the team’s five starters from last season now gone, the Blazers went from a team with championship aspirations to a lottery-bound franchise. Portland was never going to actually win a title this season, but it quickly fell on general manager Neil Olshey to chart the course from being a very good team in the brutal Western Conference that lost everything to becoming something more.

No team lost more in the last few months than the Portland Trail Blazers, but how did Olshey do in steering the franchise in a new direction? Here’s a look at Rip City’s summer with comprehensive offseason grades.