So why hasn't he won sailing's top prize? Even Jeff Gordon wouldn't win in an Edsel.

After steering two yachts that were much slower than their opponents in the 1992 and 1995 finals, Cayard finally has one, AmericaOne, that is close in boat speed to its opponent.

If he can get by Prada of Italy in the best-of-9 challenger finals, he'll have another chance in the Cup finals against Team New Zealand, the defending champion.

"The boats look pretty even. The teams look pretty even," Cayard said. "I think it's going to be tough and tight racing."

Prada won the first race by 24 seconds and AmericaOne took the second by 1 minute, 33 seconds. The third race was rescheduled for Saturday after being postponed because of light winds Friday.

Cayard, a 40-year-old San Franciscan, was skipper for the Italian boat Il Moro di Venezia when it lost the 1992 finals 4-1 to Bill Koch's America3. Three years later, he was behind the wheel of Young America when it was blown out of the water in five straight races by New Zealand's Black Magic. Both competitions were held off San Diego.

"We could have won the America's Cup against Young America even with our trial boat," said John Bertrand, the 1983 Cup winner and part of the oneAustralia team beaten by New Zealand in the 1995 challenger finals. "The U.S. defense group was well off the pace that year and Paul inherited that."

Dennis Conner headed that syndicate and handled fundraising and other management details. Now Cayard, for the first time, is in charge of a campaign and also must sail the boat.

"This has been a big toll for him," Bertrand said. "I think he's doing very, very well at it."

After more than three months of sailing in the trials off Auckland, there is the possibility of burnout before the finals, should AmericaOne get that far.

"There's always a danger of that," Cayard said. "I know in '92 we were very exhausted at the end of the battle with Team New Zealand. That's not a concern for me at this time.

"We've just got to win this round."

On the water, Cayard is an aggressive sailor.

"He just stays in your face, which is maddening," said Peter Isler, navigator on Stars & Stripes, which was eliminated in the previous round.

With a piercing stare to go with his curly black hair and black mustache, he is clearly in charge of his team. Some things, though, he has no control over.

"My biggest concern is whatever could be unknown," Cayard said, "getting in some unique or strange conditions that we haven't seen."

He has shown the ability to come back against Prada. In Thursday's second race, AmericaOne trailed by 1 minute, 49 seconds after the first of six legs but won by 1:33.

With little apparent difference between the boats, the outcome could be decided by which team has the better crew and skipper.

"This is a sailor's regatta," Bertrand said.

And Cayard is a very good sailor.

He was the first American to win the Whitbread Round The World Race, succeeding in 1998 in his first try. That earned him America's top sailing honor, the yachtsman of the year. He also has won six world championships and is in his fifth Cup campaign, third as skipper.