Conner was a rare non-billionaire fielding a team to compete in the 2003 America's Cup, held in New Zealand, receiving funding of up to US$40 million from his sponsors. His syndicate, "Stars & Stripes", suffered a severe setback before they departed California, as one of the two Stars & Stripes boats ("USA-77") sank when its rudder post failed during training. Despite raising the boat from 55 feet of water and eventually repairing it, they were unable to recover the valuable testing time lost and they were defeated in the quarter-finals of the Louis Vuitton Cup.