While he hadn't served prison time himself, Cash's drug addictions, run-ins with the law and other sufferings from his life allowed him to sympathise with the prisoners. As a fallen man, worthy of redemption, he saw himself in the people that he believed were being mistreated. Merle Haggard, (who was serving time in San Quentin at the time) said that his work for prison reform and the live shows were the turning point in his own redemption. "It didn't even matter that he was free, because there was a connection there, an identification. This was somebody who was singing a song about your personal life." - Merle Haggard on Johnny Cash Live at San Quentin.
While the association of Cash and prisoners did affiliate him with crime and wrong-doing, thus sustaining his outlaw image, he still chose to use his power to help others. He is noted to have said that at one of his prison concerts, he had the opportunity to cause a riot, and at the height of his drug addictions would have correlated with his erratic behaviour, but he still just used the performances as a chance to protest.
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