Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Chris Messina as Reese Lansing Frank Wood as Shep Pressman James Hamrick as Jesse Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Trieu Tran as Joey Phan Thomas Matthews as Martin Stallworth Charlie Weirauch as Jake Watson Wynn Everett as Tamara Hart Victoria Garcia-Kelleher as Millie Saidah Arrika Ekulona as Nia Robbie Paul Greene as Scott Kristin Carey as Ana Marie Colby Brian Konowal as Analyst Brian Tichnell as Analyst Phil Austin as Howard Worth Amy Anderson as Bethany Lee Kiran Deol as Analyst Sean Smith as Colonel Stanley Owlen