Professor Mark Orams - who will lead NZME's America's Cup analysis - was a member of Team New Zealand for the 2000 and 2003 campaigns.
Orams, who was on the TNZ weather programme, experienced contrasting fortunes as part of 5 - 0 wins and defeats in 2000 and 2003.
An infamous moment in America's Cup history, the 2003 first race loss, sticks in his mind.
"In race one of the 2003 defence, we had a really strong breeze on the Hauraki Gulf, and knew we'd have chop and current. What we hadn't predicted was the amount of cross-chop from the spectator fleet," he says.
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"We hadn't been able to simulate it or practice for it. That's when the famous two dollar bucket came out on a multi million dollar boat to bail out the huge amount of water being taken on board."
Those TNZ campaigns are part of an extensive yachting CV built up by the 54-year-old Orams, the Head of School of Sport and Recreation for the Auckland University of Technology.
Orams was a crew member on Steinlager 2 which won the Round the World yacht race, has been a national youth selector and Olympic coach, won many sailing titles himself, and his involvement in yachting related projects includes being a central figure in the Sir Peter Blake Trust.
The 'Sailing Prof's' role in our coverage will include heading our live blogs each racing day. He will also feature in video and radio station analysis of events in Bermuda.