When the Blazers started talks on Roy’s contract extension in the summer of 2009, franchise owner Paul Allen pushed for multiple contingencies to protect the organization. Nevertheless, then-GM Kevin Pritchard couldn’t handle the criticism in the Portland public and media, and eventually caved with an $82 million extension with only limited non-guaranteed money in the contract’s final year. The Blazers should’ve challenged Roy to try restricted free agency, but they didn’t have the stomach to fight that PR battle.

The beginning of the end for Pritchard came during Roy talks, sources say. Ownership felt he had undermined them with Roy and his reps, and that Pritchard didn’t back up their tough initial starting point in the talks. Before Roy’s extension was done, Pritchard was largely taken out of the discussions, and Blazers president Larry Miller started to gain control of basketball operations. Pritchard never recovered within the organization.