Age and charm make the Expert Trophy quite special. Originally called the Expert Challenge Cup, it is an ornate silver pitcher, 8-1/2 inches tall, that was donated to the Yacht Club in 1892 by Julian M. Rumsey. Julian M., the son of Julian S. Rumsey, the first Sheridan Prize winner, designated his trophy for challenge racing between cat-rigged sandbaggers in the 21-foot class. The first race was on August 27, 1892, and was won by Captain John Johnson Jr., who was challenged to a race after two weeks, as the rules permitted. He lost. The next race was in 1897, and a few years later the winner transferred his boat, her equipment, and the trophy to L. H. Stafford. That was the end of competition for thee decades, but in 1927 Mr. Stafford returned the trophy to the Yacht Club in response to convincing correspondence from Commodore William Nelson Pelouze. Club officers then selected the relatively new Class E to compete for the trophy and held a match in July of that year. Two years later, the Yacht Club abolished the challenge-cup system and designated the trophy for fleet competition, as it remains today. Every inch of the Expert not covered with flowers or leaves is covered with the names of winners; the base that bore the names of the most recent winners is missing. As of 2012, winners receive a plaque for one year, not the trophy itself. The skipper with his name on the Expert Trophy the most times is Brian Porter, who between 1982 and 2011 won it 13 times. In 2012 Brian’s nephew, Vincent Porter, won it with crew Coye Harrett and Griffin Rolander. Is your name on the Expert Trophy? Click here to visit the Virtual Trophy Room and find out.