Born in Philadelphia, Pennsylvania, Jon Drummond is known for being among the world’s best starters. He is also well known for what could be called showmanship or taunting depending on one's perspective. Drummond has been called the "Clown Prince" of Track and Field.
In 1991, Drummond won the 200 m at the World University Games. At the 1993 World Championships, Drummond ran the opening leg on the American 4x100 m relay team, which won the gold medal and equalled the world record of 37.40. At the 1995 World Championships, he ran the second leg on the American 4x100 m relay team, which did not finish its heat after Drummond and Tony McCall failed to complete their pass.
Drummond was the opening leg of the silver medal-winning American 4x100 m relay team at the 1996 Summer Olympics and reached the semi-finals of 100 m. In 1997, Drummond won his only US National Championships title in 200 m and at the World Championships, Drummond was seventh in 200 m. In 1999, Drummond suffered a third case of spinal meningitis but managed to recover to run the opening leg in a gold medal-winning American 4x100 m relay team at the 1999 World Championships.
At the SydneyOlympics, Drummond was fifth in 100 m and ran again the opening leg on the American 4x100 m relay team, which won the gold medal. At the 2001 World Championships, Drummond was again selected to run the first leg in relay, but suffered a torn right quadriceps halfway to passing the baton to Mickey Grimes in the first round and did not run in the final. He did however complete the pass to Grimes in first place allowing the team to continue onto the finals.
In 2002, Drummond was fourth in 100 m and won the 4x100 m relay in the IAAF World Cup.
At the 2003 World Championships, he was disqualified in the quarterfinals of 100 m for a false start. However, he contested that he did not false start, repeatedly shouting "I did not move". He delayed competition for almost an hour by refusing to leave the Paris track where the meet was being held. He protested for a period of time by lying down on the track. He eventually left the track of his own volition, reportedly in tears. It is one of a number of cases which relate to the revised false-start policies.
At the 2012 London Olympics, Drummond was the relay coach for the U.S. Track Team. The men's 4x100 metres relay team equalled the existing world record in the Olympics, though were defeated by a new world record by Jamaica. The women's team won and crushed the world record. In an event where improvements are normally recorded in hundredths of a second, the team knocked more than a half a second off the record that had stood for more than a quarter of a century.