Career
The 6"7" (201 m), 230 lbs (104 kg) Webster is a cousin of Jason Terry. Considered a five-star recruit by Rivals.com, Webster was listed as the Number. 4 shooting guard and the Number.
5 player in the nation in 2005.
He had made a commitment to the University of Washington, but opted to go prep-to-pro. Webster was selected by the Blazers with the sixth pick in the 2005 National Basketball Association draft after the Blazers" traded down their third pick to the Utah Jazz just hours before the draft.
He was assigned to the Fort Worth Flyers of the National Basketball Association Development League by the Blazers in January 2006, and in doing so became highest drafted player (6th overall) to be assigned to the Doctorate-League until Hasheem Thabeet. He later returned to the Portland Trail Blazers in February 2006.
He is one of the last ever high school lottery picks to be chosen in an National Basketball Association draft due to new draft eligibility rules introduced in 2006.
In October 2008, Webster signed a four-year, $20 million contract extension. On February 20, 2009, it was announced by Trail Blazers athletic trainer Jay Jensen that Webster would likely miss the rest of the 2008-2009 National Basketball Association season with a left foot injury, having only played 5 minutes during the season. Webster was traded on June 24, 2010 to the Minnesota Timberwolves in exchange for Ryan Gomes and the rights to draft pick Luke Babbitt.
Webster underwent back surgery in October 2010 and missed nearly half the 2010-2011 National Basketball Association season, leading Timberwolves General Manager David Kahn to charge the Trail Blazers with failure to adequately disclose a known injury.
Another back surgery followed in September 2011, limiting Webster to just 47 games for the Wolves in the 2011-2012 season. In the spring of 2013 Kahn"s complaint was reportedly settled by the Blazers for $1.5 million just before the matter was brought to a formal hearing before the National Basketball Association. Both teams were sworn to secrecy about the exact terms of the deal, according to basketball journalist Henry Abbott of Entertainment and Sports Programming Network. On July 13, 2012, Webster was waived by the Timberwolves.
He signed with the Washington Wizards on August 29, 2012 on a one-year, $1.6 million contract. On July 10, 2013, Webster re-signed with the Wizards.
In 2014-2015, Webster missed the first 30 games of the season after he underwent surgery in June 2014 to repair a herniated disk in his lower back.
He was ruled out for three to five months, as he returned to action on December 30, 2014 against the Dallas Mavericks. On November 20, 2015, Webster was ruled out for the 2015-2016 season after undergoing successful surgery to repair the labrum and damaged cartilage in his right hip. He was subsequently waived by the Wizards on November 30.