Gair's reputation was such that one large insurance company made it a policy to settle all cases with him out of court on the theory that trying to beat him was impossible. In one three-year period, he tried over 150 cases before the New York State Supreme Court and won all of them. Gair never attended college or law school and his formal education ended in the eighth grade. A native of New York City, he was born to Hyman and Minnie Gair on January 15, 1894 and was self-taught through law office study and through private reading of the law.