One of the NBA’s all-time enforcers, Charles Oakley is a former teammate of Michael Jordan’s on the Chicago Bulls, where he was drafted No. 9 overall out of small Virginia Union University. Three seasons later, he was traded to the New York Knicks, where he starred alongside Patrick Ewing, John Starks and others, helping the team go to the 1994 Finals.
A two-time All-Defensive player, Oak was an ironman, playing in 1,282 games over 19 seasons. But the end of the veteran’s career featured stops in several cities, including years in Toronto, Chicago (again), Washington (to play with Jordan’s Wizards) and, finally, in Houston for his final season, signing two 10-day contracts in March of 2004 with the Houston Rockets, playing in just seven more games at 40-years-old for former Knick head man Jeff Van Gundy. Amazingly, it was rumored that Oak may make a comeback in 2007, though that never materialized.
