David Letterman has been married twice – first wife Michelle Cook and current wife Regina Lasko. In 2009, Letterman revealed on his show that he had been a victim of blackmail. Someone had tried to extort money from him, saying that he would reveal Letterman’s having affairs with several of his employees if he didn’t pay him $2 million. Letterman then confirmed that the cheating allegations were true. The man blackmailing Letterman was identified as Robert J. “Joe” Halderman, a producer of the CBS true crime journalism show 48 Hours. One of the women Letterman had an affair with was his personal assistant Stephanie Birkitt. A former CBS employee named Holly Hester also came forward. As a result, Letterman dedicated a segment of his show on one episode to his wife and staff, offering them apologies and showing his gratitude for having them in his life.
— Entertainment Weekly (@EW) May 21, 2015
Letterman and his wife Lasko started dating in 1986 while he was still living with ex-girlfriend Merrill Markoe. In 2003, Lasko had a son named Harry Joseph, who is named after Letterman’s father. In 2009, Letterman and Lasko married in a small ceremony at a courthouse in Montana, where they owned a ranch. There were rumors that the two were divorcing in 2014.
As a success in entertainment, Letterman has acquired a net worth of $400 million and has had a salary of $20 million a year. According to Celebrity Net Worth, in past years, Letterman earned as much as $50 million a year. He and his wife have a 108-acre estate in North Salem, New York.