Charlie Ogletree earned first team Collegiate Sailing All-American honors in 1989 after leading the Monarchs to a fifth place finish at the ICYRA Collegiate sailing team race national championships in Chicago. He skippered ODU to first place finishes at the War Memorial regatta and the Anderson Trophy as a junior.

Since graduating from ODU, Ogletree has represented the United States three times as a member of the Olympic teams.

In the games in Athens, Greece he teamed with John Lovell to win the silver medal in the Tornado sailing class finishing second to defending gold medallists Roman Hagara and Hans Steinacher from Austria. The duo finished eighth in 1996 and seventh in 2000.

The Houston, TX. Native graduated in 1989 with a degree in English.