 At the 2008 Las Vegas Summer League, he earned the Most Valuable Player award after leading the league in scoring at 29.8 points per game and leading the Trail Blazers to a 3–2 win/loss record.Bayless scored a career-high 31 points on December 23, 2009 against the San Antonio Spurs, setting a franchise record for points by a Trail Blazer making his first career start.Bayless was traded by the Trail Blazers to the New Orleans Hornets in exchange for a 2011 first-round draft pick that would become Tobias Harris on October 23, 2010.