On October 4, 1970, two-and-a-half months after Grossman was dealt a blow by the dissolution of his contracts with Dylan, his most famous remaining client, Janis Joplin, died suddenly from a heroin overdose. Grossman refused to speak about her death to journalists or colleagues in the music business, leaving his employee Myra Friedman to handle the phone calls that flooded their office. According to Joplin biographer Ellis Amburn, Grossman's "feelings about the loss of his most valuable client are not known." What is known is that in 1974, by which time his only living clients were the members of The Band, he kept busy with Joplin's legacy. The San Francisco Associated Indemnity Corporation challenged him on his collection of $200,000 from his life insurance policy, which led to a bizarre civil trial in the spring of that year, covered by the "New York Post", in which the insurer tried to prove that the singer's death was a suicide, not an accidental overdose as had been determined by Dr. Thomas Noguchi. Grossman testified that he had never known the extent of Joplin's substance abuse when she was alive, and that he secured the accidental death policy "with air crashes in mind." He won the case and collected $112,000. In 1974 he also assisted Howard Alk with the creation of the feature-length documentary "Janis", locating and using black and white film footage in which the singer says she is satisfied with Grossman as her manager.