A 6 ft 5 in (1.96 m) shooting guard, Kittles played for the New Jersey Nets and the Los Angeles Clippers in an NBA career that spanned from 1996 to 2005.

Kittles was named the Big East Conference Men's Basketball Player of the Year in 1995 and was a consensus first-team All-American in 1996.

He holds Villanova's all-time record for most points scored (2,243), was inducted into the team's Hall of Fame, and had his #30 retired.

He led St. Augustine to a 66–5 record in his last two seasons while also earning first-team all-metro and all-state honors under head coach Bernard Griffith.

The team defeated John Ehret High School in the 1992 Class 5A state championship game.

[2] After finishing high school, Kittles attended Villanova University and played for its Wildcats basketball team.

[3] Kittles contemplated on transferring when head coach Rollie Massimino left for UNLV before his freshman year.

New head coach Steve Lappas flew to New Orleans the day after he was hired to convince Kittles to stay at Villanova.

[11] Kittles made the NBA All-Rookie Second Team for the 1996–97 season, after averaging 16.7 points, 3.9 rebounds, 3 assists, and 1.9 steals a game.

He posted three seasons shooting over 40 percent from the three-point range and helped Jason Kidd to take the Nets to back-to-back NBA Finals appearances in 2002 and 2003.