Following an eight-year career with the Eagles, in which he earned two Pro Bowl selections in 2004 and 2007, Westbrook signed with the San Francisco 49ers, for whom he played in 2010.

[1] Westbrook attended DeMatha Catholic High School in Hyattsville, Maryland and was an excellent student and a letterman in football and basketball.

[7] Westbrook saw limited time in the 2002 season, but he threw a touchdown pass to wide receiver Todd Pinkston on a trick play in a September 2002 rout of the Dallas Cowboys.

[10] He made his historical mark in the NFL in the 2003 season with a fourth quarter punt return for a touchdown to defeat the New York Giants 14–10 in the closing minutes on October 19, 2003.

Westbrook, who scored 11 touchdowns by ground and air, missed the playoffs that year after tearing a triceps muscle in the final game of the season against the Washington Redskins.

After the departure of previous starter Duce Staley and a pre-season injury to Correll Buckhalter, Westbrook became the starting running back for 2004.

Westbrook signed a five-year contract extension with the Eagles in November 2005, after holding out of training camp and months of hectic negotiations.

On December 6, 2005, with over 1,200 total yards rushing and receiving, it was announced that Westbrook would miss the rest of the 2005 season due to a mid-foot injury he sustained during a 42–0 Monday night loss to the Seattle Seahawks.

The 49ers' decision to sign Westbrook came after the sudden retirement of second year backup running back Glen Coffee.

[11] On November 29, 2010, during the Monday Night Football game versus the Arizona Cardinals, starting halfback Frank Gore fractured his hip, ending his season.

[14] Westbrook began the 2013 season as a panel member on Eagles Post Game Live on the Comcast Sportsnet Network, along with Michael Barkann, Ed Rendell, and Ray Didinger.

On October 19, 2015, Westbrook was inducted to the Eagles Hall of Fame during Monday Night Football versus the New York Giants.

[17] His second cousin, Jamire Westbrook plays for the Miami University in Ohio football team as a running back.