The 27th defense is the most contentious chapter in an event chronicled in controversy, and considered by many to be the low point in the history of the America’s Cup.

    New Zealander Michael Fay issued a renegade challenge, specifying a sailboat double the size of a 12-meter, and demanding the race be held within the 10 months specified in the Deed of Gift. When SDYC officials declared the challenge invalid, Fay took them to court and won the first round.

    The SDYC responded by building a 60-foot wing-sailed catamaran as the defender against Fay’s 133-foot "Big Boat." It was a laugher on the water, as Conner’s Stars & Stripes easily defeated New Zealand, 2-0.

    But things were deadly serious on shore, as the lawyers picked up where the sailors left off. Ranting "Read the Deed," Fay returned to the New York Supreme Court, trustee of the America’s Cup Deed of Gift, where he asked that SDYC’s victory be overturned. Judge Carmen Ciparick granted his request.

    Not giving up without a fight, SDYC appealed the ruling to the New York Court of Appeals, and on April 26, 1990, SDYC was finally declared the winner of the match held more than a year and half earlier.