Escalation and Confrontation (1965-1967)

The two must have reached a reconciliation of sorts because, inexplicably, Holiff stayed on Cash's manager, even though Cash's financial issues meant that Holiff had to take serious cuts to his commissions. A contract from 4 December 1965, for example, shows that he was supposed to receive a third of profits for dates booked with Variety Theater International Inc. in Duluth, Victoria, Vancouver, and Seattle, but that the contract was amended to grant two-thirds of profits to Cash instead. 

In a letter to Cash from April 1966 (right), Holiff reflected upon the five years of their association, remarking that because his expenses had increased and his commissions had been reduced substantially in that time, "I am earning less now than I was four years ago." And although he concedes that he "willingly accepted the erosion of my situation as time went by," but Holiff's decreasing commission would become a major point of contention between him and Cash as the years progressed.

But Holiff was there to help Cash face the turbulent events of 1966, including a hateful onslaught of attention from a white supremacist group following Cash's arraignment in December 1965. When a photograph of Cash and his wife, Vivian, leaving the courthouse (which had appeared in newspapers around the world) was reprinted in the Thunderbolt, the newspaper of the white supremacist National States' Rights Party, Cash had to deal with months of harassment because they thought Vivian was  African American. Likely due to the horrible emotional toll of the fire, the arrest, and the harassment by white supremacists (as well as Cash's ongoing relationship with June Carter), Vivian filed for divorce in August 1966. Holiff and Cash's accountant, Anzac Jacobs, were the ones who handled the settlement.