Telfair was picked thirteenth overall in the 2004 NBA draft by the Portland Trail Blazers on the heels of an eminent high school career playing for Abraham Lincoln in Brooklyn.
However, he later had a change of mind and went pro instead, a decision precipitated by a fatal shooting that occurred at the apartment complex where his family lived.
On January 1, 2005, Telfair scored 14 points on five-for-eleven shooting, making four of five free throws to go with five rebounds and five assists with one turnover.
Under new head coach Nate McMillan, Telfair began the 2005–06 season as the starting point guard and was occasionally paired in the backcourt with another high school draftee taken in 2005, Martell Webster.
In December 2005, Telfair suffered a thumb injury and was replaced in the starting lineup by Steve Blake, who went on to have fewer turnovers and more assists.
Although the Trail Blazers had already been eliminated from playoff contention that season, Telfair scored the game-winning basket against the Houston Rockets on April 5, 2006.
[8][9] On July 31, 2007, the Celtics traded Telfair, along with Al Jefferson, Gerald Green, Ryan Gomes, Theo Ratliff and two first-round draft picks, to the Minnesota Timberwolves for Kevin Garnett.
On July 20, 2009, Telfair was traded to the Los Angeles Clippers along with Craig Smith and Mark Madsen in exchange for Quentin Richardson.
[12] On July 26, 2010, Telfair was traded back to the Minnesota Timberwolves, along with Delonte West, for Ramon Sessions and Ryan Hollins.
[23] The following night, Telfair left a pre-season basketball game against the New York Knicks at Madison Square Garden to observe a police lineup, but he did not identify any of the potential suspects.
[24] Telfair and a friend, Al Eden Fuentes,[25] were arrested early on April 20, 2007, and charged with felony possession of a weapon.
Inside the vehicle, officers spotted a lit joint, and a subsequent search yielded three loaded handguns, a semiautomatic rifle, a ballistics vest, and several bags of marijuana that were among suitcases, clothing, shoes, and furniture parts.
[28] Sebastian was in New York at the time for what was supposed to have been only a matter of hours, being in between a move of residence, and for the opening of basketball courts at the Coney Island projects where he was raised.
[31] Reported by ESPN from an October 7, 2021 indictment, eighteen former NBA players, including Telfair, Jamario Moon, Glen Davis, Tony Allen and Darius Miles, were arrested on charges alleging they defrauded the league's health and welfare benefit plan out of about $4 million.
According to the indictment, the former players engaged in a widespread scheme to defraud the plan by submitting false and fraudulent claims to get reimbursed for medical and dental expenses that were never actually incurred.
His younger brother Ethan Telfair, who likewise featured in the documentary film, played basketball at Idaho State.