Career
He has been the Chef de Mission (the head of the Australian delegation) at the 1998 Nagano, 2002 Salt Lake City and 2006 Torino, 2010 Vancouver and 2014 Sochi Olympic Winter Games. He was the General Manager at the 1994 Lillehammer Games, being Deputy to Geoff Henke. Australia had broken new ground during Chesterman"s time in the upper reaches of winter sports administration.
Australia’s maiden gold medal came in highly unlikely circumstances.
In 2006 in Torino, Australia sent 40 athletes to compete in 10 sports, a record number of competitors and events, and Australian officials publicly declared their expectation of winning medals. In 2010 in Vancouver, Australia had its most successful Winter Games, winning two gold (Torah Bright in Snowboard Halfpipe and Lydia Lassila in Aerials Skiing) and one silver (Dale Begg-Smith in moguls).
Chesterman has been reappointed Chef de Mission for the 2018 PyeongChang Australian Olympic Team. Currently a resident of Launceston, Tasmania, Chesterman is managing director of Sportcom Pty Limited, a communications and events company he founded in 1988.
The company also has offices in Melbourne and Launceston.