After the war, Wynshaw married Frances Greenberg, who went to Cooper-Union to study art. Later on, he and Frances moved to Manchester CT, where he opened a bridal shop. In 1956, the Wynshaws moved to Los Angeles, where David was hired by CBS Records as a west coast sales representative. In 1963, he was named CBS branch manager for New York.
Wynshaw worked on artist relations, and was said to be involved in signing a number of well-known artists including Santana, Chicago, Billy Joel, Bruce Springsteen, and Janice Joplin. Riding the coattails of his boss, Clive Davis, who became president of the company in 1967, Wynshaw became a key figure at CBS records, eventually being appointed Senior Director of Special Events. Along the way he became known as “Mr. Gotcha”–anything an artist needed, he would get for them on short notice, no questions asked. "Two tickets to a Knicks game 15 minutes before tipoff? Front-row seats at the Copa when Tony Bennett’s in town? Fly 700 people to a Vegas convention in the middle of an airline strike? Gotcha could get anything," said an article in Vanity Fair . Far Paul Simon described Wynshaw as "Clive's procurer."
In 1973, Davis fired Wynshaw after "Mr. Gotcha" was named in an FBI investigation of payola, embezzlement and other financial wrongdoing. Davis himself was fired later that same year as a result of the scandal. He was accused of using CBS funds to finance his personal life, including an extragavant bar mitzvah party for his son.
Diavis bounced back after the scandal and founded his own record company. Wynshaw ultimately served a year jail sentence for conspiracy and mail fraud.
Davis blamed Wynshaw for any wrongdoing, but Wynshaw, in a 2000 interview, said, “Everybody knows I took the fall for Davis.”
The Wynshaws divorced in the aftermath of the scandal, and David moved to Florida, where by 1977 he was VP and General Manager for Tropical Record Distributors in North Miami. In an article in Rolling Stone magazine, his former personal assistant said that he “presented a diamond pinkie-ring image, but he wasn’t a seedy character... He was a good person and probably didn’t deserve the treatment he got.”
David Wynshaw died on May 5, 2006 in Miami, and is buried in Kensico Cemetery, Valhalla NY, in the Friars’ Club plot.