The Trail Blazers president has apparently convinced owner Paul Allen the former is more representative than the latter.
Adrian Wojnarowski of ESPN:
Olshey has a strong résumé, dating back to his time with the Clippers. Portland is in good hands with him.
Olshey’s mid-season trade for Jusuf Nurkic lifted the Trail Blazers out of an expensive malaise and might have turned momentum toward this extension. Now, Olshey must negotiate an extension with Nurkic and – despite the massive payroll formed by his mistakes last summer – keep finding ways to surround Damian Lillard and C.J. McCollum with more talent.
It won’t be easy, but I’d rather keep Olshey in charge than take a chance on an unproven executive.