The year 1964 was an important one for Cash: he became successfully associated with the folk movement with the release of his album Bitter Tears: Ballads of the American Indian and for an acclaimed performance at the Newport Folk Festival, where he also met Bob Dylan for the first time (whose song "It Ain't Me, Babe" he recorded the same year). In a 23 May 1964 letter to Cash, Holiff noted that sales for the single "Understand Your Man" had surpassed a million, and sales for the album "Ring of Fire" were approaching a quarter of a million. "I believe that as every day passes by you are moving closer to America's foremost singing story teller in fact as well as name," the letter reads, "and that you will come to be regarded as an artist of the very top rating with no special affinity to any particular facet of the music industry." 

By late October, Cash wrote to Holiff with changes he wanted to implement to the show, notably cutting down on "hillbilly" acts and raising salaries for June and Maybelle Carter and the Statler Brothers (whom Holiff had started managing that year and who would release their major pop hit "Flowers on the Wall" the following year). "And Saul," he writes, "This will destroy you.........Take $1000.00 bonus for yourself. You're the best agent - promoter, manager, etc in the world." The two were back on good terms.

But it would not last. By March 1965, as Cash's addiction worsened, he was missing more shows than ever. A meticulous record-keeper, Holiff drafted an event log for March 17-23 that details all Cash's missed appearances on a tour through the northeastern United States and offers a short but illuminating snapshot into Holiff's life managing Cash at this point.

Attempting to perform damage control from London while Cash was on the road, Holiff recorded not only the dates but the times of calls during this stretch, and the log shows that he mostly spoke to people around Cash rather than Cash himself. There were calls from Luther Perkins, Marshall Grant (Cash's guitar and bass players), and Andy Serrahn (the tour promoter) and calls to June and Maybelle Carter.

Only on the last days recorded in the log did Holiff finally receive communications from Cash. On March 22, Cash sent two telegrams instructing Holiff to cancel several shows; then, in an abrupt and likely frustrating turnaround, he called him on March 23 telling him that he would in fact play the shows.

Despite the tension between them, however, Holiff still sought to preserve Cash's reputation publicly. He printed an "Eviction Notice" advertisement to address and dispel "'Rumors' In Our House," which begins by asserting that "The only rumor about Johnny Cash that is true . . . is that he sells out wherever he appears."