The 2011-12 campaign marked Olshey's second season as the Clippers' Vice President of Basketball Operations and his ninth overall season with the organization. Olshey began his career as Director of Player Development prior to the start of the 2003-04 season and served as an assistant coach during the 2004-05 campaign before holding the title of Director of Player Personnel from 2005-08. Olshey was promoted to the role of Assistant General Manager prior to the start of the 2008-09 season, holding that position for two seasons until being named Vice President of Basketball Operations prior to the start of the 2010-11 campaign.
After spearheading an exhaustive search that brought the Clippers new head coach Vinny Del Negro prior to the start of the 2010-11 season, Olshey retooled the roster prior to the start of the 2011-12 campaign. During a six-day span, Olshey added two-time All-Star Caron Butler, five-time All-Star Chauncey Billups, re-signed athletic center DeAndre Jordan and through the biggest trade in franchise history, brought in All-Star point guard Chris Paul. In addition, without a first round selection in the 2011 NBA Draft, Olshey was still able to solidify the Clippers bench by nabbing Georgia teammates Trey Thompkins (37th overall) and Travis Leslie (47th overall) in the second round. In addition to these moves, Olshey made three key acquisitions with the free agent signing of veteran big men Reggie Evans and Kenyon Martin and the trade deadline deal to acquire swingman Nick Young from the Washington Wizards. Adding these players to the returning core of 2011 NBA Rookie of the Year Blake Griffin, All-Star point guard Mo Williams, 2011 All-Rookie Second Team guard Eric Bledsoe and solid rotation players Randy Foye and Ryan Gomes, the Clippers had one of the deepest rosters in the NBA this season.
Prior to joining the Clippers, Olshey served as Director of Player Development for SFX Sports Group, Inc. where he created, organized and conducted Pre-Draft and Off Season Training Camps for future and current NBA players. The Pre-Draft Camps produced 15 Lottery picks, 25 First Round selections and 57 NBA players. Participants in Olshey's Off Season skill development clinics include more than 85 current NBA players including numerous All Stars and All-NBA selections. He has also served as a Head Coach/Clinician at the Reebok ABCD Camp, the Roundball Classic and numerous NCAA basketball camps throughout the country.
Upon graduation from LeMoyne College in 1987 he was honored with the "Outstanding Senior Athlete" Award. Olshey and his wife Leslie reside in Manhattan Beach with their sons Connor and James.