Personal life

From around 1967 to 1975, Silverstein lived on a houseboat in Sausalito, California. He also owned homes on Martha's Vineyard, Massachusetts; Greenwich Village, New York; and Key West, Florida.[34] He never married, and according to the 2007 biography A Boy Named Shel, had sex with "hundreds, perhaps thousands of women".[2] He was also a frequent presence at Hugh Hefner's Playboy Mansion and Playboy Clubs.

Silverstein met a woman from Sausalito named Susan Taylor Hastings at the Playboy Mansion,[35] and they had a daughter named Shoshanna Jordan Hastings (b. June 30, 1970).[36] Susan died on June 29, 1975, one day before Shoshanna's fifth birthday,[36] and Shoshanna went to live with her uncle and aunt in Baltimore, Maryland.[35] Shoshanna died of a cerebral aneurysm on April 24, 1982, at age 11.[37] Silverstein's 1981 book A Light in the Attic is dedicated to her.[35] Silverstein later met Key West native Sarah Spencer, who drove a tourist train and inspired Silverstein's song "The Great Conch Train Robbery".[38][39][40] They had a son named Matthew De Ver (b. November 10, 1984),[41] who later became a New York City–based songwriter and producer.[42]