Tupac Shakur signed his Death Row Records contract inside a New York prison and told a corrections officer he didn’t care if the devil himself got him out.
That’s the claim made by Michael Christopher, a former corrections officer at Clinton Correctional Facility, who recounts his personal interactions with Shakur during the rapper’s 1995 incarceration in his memoir Tupac Behind Bars.
According to Christopher, Tupac Shakur was visibly excited the day he inked his deal with Suge Knight and attorney David Kenner, who visited him at the prison to finalize the contract. The agreement secured his $1.4 million bail and brought him into the Death Row fold.
“He came over to my desk, which he did quite often,” Christopher said. “He showed me the contract because he was pretty proud of it. And he goes, ‘Do you know what this is?’ And I’m like, ‘No.’ And he’s like, ‘I just signed a contract with Death Row, and that’s Suge Knight, and blah, blah, blah. I’m going to get the money for my bail.’”
Christopher congratulated him, but added a warning: “Just be careful because you might have sold your soul to the devil.”
Shakur laughed and responded, “Oh, you mean like Robert Johnson, right? At the crossroads?”
Christopher confirmed the reference, telling him, “Just be careful because he might call in his chips.”
Shakur didn’t flinch. He replied, “I don’t care if I signed a soul with the devil. As long as the devil can get me out of here, I don’t care who I sign with.”
Christopher believes that moment stuck with Shakur, especially since he later received a rare photograph from the rapper with the phrase “See you at the crossroads” written across the top.
The phrase echoes the legendary tale of blues musician Robert Johnson, who, according to folklore, met the devil at a crossroads to trade his soul for musical genius.
Christopher, who spoke with Tupac Shakur during visits and downtime, said the rapper was well aware of the Johnson legend.
“He was quite familiar with Robert Johnson already anyway,” Christopher said. “So he was like, ‘Damn.’ He says, ‘Yeah.’ He says, ‘I guess maybe.’ But he said he wasn’t worried.”
Johnson’s story has long been part of American music mythology.
According to the legend, he left town as a mediocre guitarist and returned a year later with unearthly skills. The price for that talent, the story goes, was his soul—and Johnson died young, at age 27.
Christopher said he saw a parallel in Shakur’s situation.
“He left town for a while, and then I think it was like a year or so later, the devil cashed it in,” he said, referring to Johnson. “And eventually he had died young. And I was just concerned with Tupac about the same kind of parallel.”
At the time of their conversation, Shakur was in the middle of serving a sentence for sexual abuse. The financial burden of incarceration had taken a toll on him, and he had shared his struggles with Christopher.
“I knew that being in prison had financially strained him somewhat,” Christopher said. “He had told me he was going through a lot of money.”
That’s why, when Shakur returned to the visiting area after signing the contract, Christopher remarked, “Looks like you’re back in business.” He grinned and replied, “Yeah.”
Christopher’s book, Tupac Behind Bars, is billed as the only title focused solely on the rapper’s time at Clinton Correctional Facility.
It offers a first-person view from a corrections officer who says he earned Shakur’s trust, delivering stories from inside the prison walls that explore how the Hip-Hop icon coped with fame, pressure and confinement.
The memoir avoids a traditional biography format and instead presents a narrative account of daily life behind bars, including Tupac’s interactions with staff and other inmates.
Christopher’s recollections add another layer to the complex story of Tupac Shakur’s time with Death Row, a label that would both elevate his career and entangle him in deeper conflicts.
Shakur was killed in a drive-by shooting in Las Vegas in September 1996, less than a year after his release.
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