Born in New York City in 1933, Sherwin attended Stuyvesant High School, Columbia College (Phi Beta Kappa) and Columbia Law School. He graduated from the U.S. Coast Guard Academy Officer Candidate School in 1956 and later became a Lieutenant Commander. He is an attorney admitted to the New York and Supreme Court Bars. He joined GAF Corporation in 1960 serving in various legal and operational roles and eventually becoming its Chief Financial Officer. He was CFO at Triangle Industries from 1983 to 1984, rejoining GAF Corporation as Vice Chairman from 1985 to 1990.
While at GAF, in 1988, he was indicted by the US Attorney for the Southern District of New York, Rudolph Giuliani, for stock manipulation in connection with the 1986 sale of stock owned by GAF. He was convicted after three trials, but the conviction was reversed on appeal and dismissed with prejudice. In 1991 he was appointed Executive Vice President and Chief Financial Officer of Hunter Douglas N.V., a Dutch multinational company, in which capacity he served until 1999. Since then he has been a Director and an adviser to Hunter Douglas.
He is an Overseer of the International Rescue Committee and member of the Association of the Bar of the City of New York. He received an Honorary Doctor of Laws Degree from the University of Bath in December, 2007.
In chess, Sherwin finished third and tied for third in the US Chess Championship four times and tied for fourth three times. He was Intercollegiate Champion and New York State Champion in 1951 and US Speed Champion in 1956–57 and 1959–60. He earned the International Master title in 1958. He played in the Portorož Interzonal in 1958, which was part of the 1960 World Championship cycle. While he finished only 17th out of 21 players, he scored (+2–2=2) against the six players who qualified from the tournament to the Candidates tournament at Bled 1959. He is a previous President of the American Chess Foundation.
- Gaige, Jeremy (1987), Chess Personalia, A Biobibliography, McFarland, p. 388, ISBN 0-7864-2353-6
- Gaf Accused Of Scheme On Carbide Stock
- Appeals Court Reverses Gaf, Exec`s Convictions
- Lawyer Arthur L. Liman (Public Affairs 1998), Chapter 18.
- Fischer, Robert. My 60 Memorable Games. (Faber & Faber Limited 1969) Game 1