Sylvester was born February 2, 1893 in New York City, New York, the son of Italian immigrants Alfonso and Philomena Sylvester. His father worked at a factory that made pianos. Not unlike the majority of golfers from his generation, Sylvester first learned to play golf after working as a caddie. He was also a fine maker of golf clubs.
Golf career
At age 17, Sylvester won the Greater New York Championship at the Van Cortlandt Park links, defeating William Wallace. Sylvester played in a number of U.S. Open tournaments. His results were as follows: T45 in 1913; 50th in 1915; T44 in 1921; and T24 in 1923. Sylvester was hired as the professional at the Glens Falls Country Club in Queensbury, New York, in 1914 but spent only one season there. He then took a post as club professional at St. Albans Country Club in Queens, New York, from 1915 to 1938. In 1939, Sylvester was the head professional at the Pomonok Country Club on Long Island where that year's PGA Championship was contested. As the home professional, he was exempt from qualifying. For reasons unknown, however, the official records for the tournament do not reflect Sylvester as being in the starting field. Sylvester's golf career was put on hold when he was called up for duty to serve during World War I. It was reported in the Brooklyn Daily Eagle on November 29, 1918 that Sylvester was wounded when he was shot in his calf while fighting in France. The report went on to say that Sylvester did not think the wound would affect his professional career and that he had done more teaching than playing since his 1913 appearance at Brookline. In 1936 he was paired with Babe Ruth in a pro-am best-ball tournament at the Rockville Country Club on Long Island. Sylvester's game suffered as he was "distracted" by the large crowds that followed Ruth.
Sylvester had his best major championship finish in the 1920 PGA Championship which was played from August 17–21 at the Flossmoor Country Club outside Flossmoor, Illinois, a suburb south of Chicago. The field of 32 golfers qualified by sectional tournaments. They then competed in 36-hole match play rounds in a single-elimination tournament. Sylvester opened up play with a first round victory over Tom Boyd, winning 4 and 3. In the next round, however, he lost convincingly to James Douglas Edgar by the score of 11 and 9. Sylvester's final position in the tournament was a tie for ninth place, winning $60.
Sylvester died on October 28, 1976, presumably in New York state. Sylvester was a frequent competitor in both the U.S. Open and the PGA Championship. He was granted a patent for a golf club design in 1937.
Results in major championships
Note: Sylvester never played in the Masters Tournament or The Open Championship. NYF = Tournament not yet founded NT = No tournament DNP = Did not play ? = Unknown R64, R32, R16, QF, SF = Round in which player lost in PGA Championship match play "T" indicates a tie for a place Yellow background for top-10.