Tommy Tailer was one of the game’s first prodigies. The son of New York businessman T.S. Tailer Sr., one of the early leaders at Newport Country Club, he won the RIGA Junior Amateur in both 1927 and 1929 and was upset for that title in 1928 by Joe Pezzullo. Tailer won the State Amateur in 1930, ’31 and ’32 and captured the State Open in both 1932 and ’35.
A resident of New York who spent his summers in Newport, Tailer also won numerous championships in New York. In 1932, he not only won the Rhode Island title, but also won the Metropolitan Golf Association title in New York and reached the quarterfinals of the U.S. Amateur.
He qualified for match play in the U.S. Amateur at 16, making him the youngest player ever to accomplish that feat to that point. His father built a nine-hole course, Ocean Links, adjacent to Newport Country Club, to give his son a place of his own to play. The course, which existed from 1921-1931, has been called the finest nine-hole course ever built in the United States.
The Golden Mashie, a tournament held at Ocean Links, was the predecessor of The Masters in drawing the top amateurs from around the country. Tommy Tailer played so well he earned two invitations to The Masters. In 1938, he became the first amateur to break 70 in The Masters.