How Prison Transformed Tupac But Could Not Save Him From Death Row

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On Valentines Day 1995, Tupac Amaru Shakur was processed into general population at Clinton Correctional Facility. Approximately eight months later, Pac left the maximum security prison in Dannemora, New York. And nothing was the same.

From his cell, Tupac counted his time. Unless he had visitors, Pac was in isolation for a reported 23 hours a day. In that countdown, he began campaigning against those he felt betrayed him while pivoting towards his future. When stepped off the plane back to California (as portrayed in All Eyez On Me, in theaters this Friday, June 16), he was deeply changed. From time served to living on borrowed time, Shakur’s transition behind the walls was seismic. He quickly went from punitive solitude to fighting for space. Forever more, he’d be a man apart.

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In theory, Clinton Correctional Facility (aka APPU) represented a hard reset for the man who turned 24 years old while on his bid. “I was cultivated in prison, my embryo was [incarcerated],” Shakur said in a 1995 interview, correcting a legend that he was in fact born behind bars. The storied dichotomy (perhaps contradiction) that is Pac dug in deep: He said he read Maya Angelou and The Prince. He claimed listening to Dionne Farris and Rappin’ 4-Tay, he received letters from Treach and Tony Danza. All the while, Pac apparently toiled with what revenge really means: living one’s best life, or sending enemies to their demise.

Up until I got shot, I thought that no Black person would ever shoot me. I was their representative. I believed that I didn’t have to fear my own community. I represent them. I was their ambassador to the world,” Pac said a month before being “out on bail, fresh out of jail.” Laying in several Manhattan hospitals, Pac recalled his mind state. “I just thought about how I would change; what would I do? How can I make them sorry that they ever did this to me? How can I come back like 50 times stronger and better?

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He sat with that question at Rikers Island, and eventually Clinton. There, he told Sanyika Shakur (aka Monster Kody) just days after his release that he believed his accusers were in cahoots with those who shot him five times in a Manhattan studio lobby. In 1995, Tupac Shakur was convinced that some people wanted him off the streets. He could not be killed, but he would be convicted. Inside, the artist scored his first #1 album and single. At the same time when Pac felt victimized, his name could not be ignored by Billboard or the Hip-Hop community that he felt shunned him. “I think I’ve been attacked more than I deserve. But that’s all good to me, ’cause I  always been a fighter. I always been a solider. I always been a struggler. Can’t nothing stop me but death itself,” he said of his damaged public image, while serving.

Convicted of sexual assault on a woman, Pac’s sensitive side attempted to change the conversation. “Dear Mama,” perhaps his best known work, was a pilgrimage. It brought Pac back to his “Keep Ya Head Up” roots. The hit reconnected him with the closest thing he had to a constant in his life: his mother. Additionally, it told the world that mother-and-son were two misunderstood souls who weren’t scared of jail, sensitivity, or anything else. From the cell, he self-compared to Vincent Van Gogh and Marvin Gaye—fellow tortured souls, and undervalued creatives.

With transformation came palpable change. In prison, Pac grew out his hair (he had to, with no razors around). He also penned a screenplay, worked out, and played football in the yard (including with Joey Fama, one of the men convicted and sentenced for the killing of Yusef Hawkins). The superstar also got married while inside. Shakur and longtime girlfriend Keisha Morris wed on April 29, 1995. Not permitted conjugal visits, Tupac settled for company, love, and loyalty (and he did apparently try his hand at some erotic letter-writing too). His bride reportedly moved from the city just to be closer to her husband.

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Like many prisoners, Shakur experienced racism. In a letter sent Death Row Records employee Nina Bhadreshwar, the rapper claimed corrections officers were calling him “nigger” regularly, without monitor. He echoed that, to Sanyika Shakur (whose memoir was also cited as an important prison text to Pac). “[When I arrived], these mothaf*ckas were callin’ me ‘nigger;’ I’m buggin’ out. I never had no white people callin’ me nigger and nothing happened [in response]. In this jail I was at, you get seven years if you touch the [officers], no matter what.” The rapper who had been scrutinized for his actions and words against officers of the law was initially led to a bloody mattress on a cot, in a barren cell. He would later recount fellow inmates bringing him food, as well as weapons and drugs (which he refused), and items to help Clinton’s highest profile inmate with his stay.

Although Shakur faced racism and hatred, he felt particularly harmonious. While prisons are often thought to be racially divisive, Pac credited that time as an awakening. The former Baltimore arts school student made friends with folks of different hues, walks, and backgrounds. “[Before], I was letting people dictate who should be my friends. I felt like because I was this big Black Panther type of ni**a, I couldn’t be friends with Madonna. And so I dissed her, even though she showed me nothing but love. I felt bad, because when I went to jail, I called her and she was the only person that was willing to help me, of that stature. Same thing with Mickey Rourke-he just befriended me. Not like ‘Black and white,’ just like friend to friend. And from now on, it’s not going to be a strictly Black thing with me. I even apologized to Quincy Jones for all the stuff I said about him and his wives.” In one breath, Pac was having an awakening, and showing a more self-aware and forgiving side completely different from the previous five years of his career. However, while Shakur made connections with various types of people, he acknowledged also making a multitude of enemies by claiming “West Side!” in a crowded New York jailhouse.

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Twenty years after his death, Pac remains Rap’s biggest prisoner. The artist sentenced the 18 months was surrounded by long-term inmates, serving 60 to 80 years. From the inside, the son of a Black Panther provided keen insights on the prison industrial complex. “Jail is big business. Believe me… I’m in jail. I see the big business. They charge you for your telephone calls. They charge you for disciplinary problems…you can feed a whole town off of one jail. This  jail is in the middle of a town that feeds everybody; everybody works here. This is the main income.” He warned, “If we don’t start peeping that, we in trouble.”

More than just prison system economics, he wanted his fans to take heed. “When I was young, I couldn’t wait to go to jail,” he admitted. “Now that I’m here… this is not the spot. I know that everybody go to jail come out and say, ‘This ain’t the spot,’ but this is not the spot!” Besides marching to a created regiment, Shakur watched his peers perish just like on the streets. “You can die here. Just yesterday, a dude was murdered. He wasn’t in here on no murder [charge]. This dude was here on a drug [charge]. He’s gone, he’s dead… in jail, by another prisoner who had life. He had nothing to lose.” Newly married, at the then-peak of his career, Tupac Shakur had more to lose than ever before.

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He planned. “We need to start figuring out another way. Now, if we do want to live the ‘Thug Life’ and the gangsta life and all that…stop being cowards and let’s have a revolution. But we don’t want to do that. Dudes just wanna  live a character. They wanna be cartoons. But if they really wanted to do something, if they was that tough, [we could] start our own country.” Tupac had plans on appointing delegates, in the cities and communities, to patrol. He spoke about them several times during 1995, using gangs and powerful leaders to regulate the drug dealers. Pac wanted those using the ghetto to pay for its improvement–recreation centers, parks–and use assigned hours. The man who was convinced that fear outlasted love wanted to flex it on wrongdoers.

With these plans, Tupac was adamant that Thug Life had turned a page. Going inside, the media used the mantra, the group, and the ink against him. “When I said, ‘I’m living the Thug Life,’  believe me… it was all real. As sure as ‘Thug Life’ is tattooed across my  stomach, it will always be a part of me. But ‘Thug Life’ is like the twelfth grade. Some  people graduate from high school and don’t seek to do anything else. So they continually live the ‘Thug Life.'” Pac, who once declared that his dream was to attend an actual college which he could not afford, planned on turning the page. “I wanted to go to college. Not college in [the sense of] a school or university, but college in life. I wanted to move up. So I wanted to do something different. I wanted to expand. I wanted to grow…So what I would tell anybody who would listen to me is that…you got to start peeping game. Peeping the game. The game is the game of life.”

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In his letter to Death Row Uncut magazine, Shakur mapped out his steps beyond Thug Life in mid-’90s street terminology. “When a normal man questions his existence, it begins with childhood, teenager, adult. However, when most Black males examine their lives, especially those of us from ghetto upbringing realize this is not our development stages. Ours begins with a young dustkicker, a thug ni**a, then finally a boss playa. Each stage has heavy obstacles and pleasure, but they are all lethal if not played properly,” he writes. “I challenge all of the Souljahs of this nation 2 examine and evaluate your lives. Are U Ready 4 the Next  Level? I did not begin Thug Life I just personified it. I couldn’t stop it if I tried but in my heart the thug ni**a has advanced 2 be a Boss Playa. So no Thug Life is not dead but in my heart it is,” he wrote. In another passage, he defined the next level. “A regular playa plays women. A Boss Playa plays life. A Boss Playa is a  thinker, a leader, a builder, a moneymaker, a souljah, a teacher and most of all a Man! I want all of my  homiez 2 realize there is another level it takes heart and courage 2 stand alone face the demons and  make a change! We are powerful people but not unless we have power and if we all die we have nothing. No Powers No Money, No Life, Nothing.

In another conversation, with Kevin Powell, Pac provided some glimpses into just what those plans looked like: “I’m going to start an organization called Us First. I’m going to save these young ni**as, because nobody else want to save them. Nobody ever came to save me. They just watch what happen to you. That’s why Thug Life to me is dead. If it’s real, then let somebody else represent it, because I’m tired of it. I represented it too much. I was Thug Life. I was the only ni**a out there putting my life on the line,” Shakur told VIBE. Us First was planned to be a collaboration between Pac and ally Mike Tyson, as well as Sanyika Shakur. That would be the person Pac called a reported two days after release that October. In the call, they planned youth sports leagues (funded by rappers) and the organized neighborhood regime. Pac wanted to integrate faith groups, generations, and give everybody a purpose.

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While leadership and revolution were heavy on Pac’s mind in autumn of 1995, music was less so. He wrote just two songs while serving, and only one of those would reportedly make All Eyez On Me (an album recorded in less than half of a month). “Everybody’s like, ‘Aw man, he’s in a jail now. He gonna come out with a bomb album,’ but it’s the opposite. Prison kills your spirit. Straight up. It kills your spirit. There is no creativity. There’s none of that,” he said shortly before his release. “I only recently started writing.” However, the Interscope Records flagship artist was mapping out his album personnel. When he wrote Chuck D from inside, that was deeply apparent.

Shakur was envisioning songs with Sister Souljah and Public Enemy’s front man. Even ahead of One Nation plans in 1996, Pac was clearly not out to destroy a coast, as so often thought. “As far as foes and enemies and all that…I really don’t care,” Pac said in September of 1995, well after his fiery VIBE interview. “My only fear of death is coming back reincarnated. I don’t have no negative feelings towards nobody. It’s not like I’ma get out and shoot somebody up.” He was simply California dreamin’ from a cold cell. He sought out mentors.

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While Chuck D was a positive one, other mentors would likely encourage some of the negative actions and remarks that followed. However, Pac was still sorting out his own feelings. “I know who shot me. I don’t care about telling the police none of that…I’m still here… and it’s not like I’m untouchable. I know I can be killed as soon as I get out of there. But I’m cool. I go screaming ‘West Side,’ and I’m all good.” In a cold New York cell, Pac was California dreaming right up until he stepped off that jet.

Pac signed the aforementioned letter to Death Row Uncut with the closing, “Until The End Of Time.” That would be one of his better posthumously released choruses and song titles. As he sat waiting, perhaps Shakur looked at the units of time differently. He had prognosticated his death on Me Against The World. This very mortal man was focused on immortality through purpose and legacy. As his words to VIBE signal, Pac was in a martyr’s mind state. With the prospect of death lingering, it appears that what Pac wanted more than anything was simply a chance live and exonerate himself with whatever he had left of a candle burning at both ends:

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This is God’s will. And everybody that said I wasn’t nothing…my whole goal is to just make them ashamed that they wrote me off like that. Because I’m 23 years old. And I might just be my mother’s child, but in all reality, I’m everybody’s child. You know what I’m saying? Nobody raised me; I was raised in this society. But I’m not going to use that as an excuse no more. I’m going to pull myself up by my bootstraps, and I’m going to make a change. And my change is going to make a change through the community. And through that, they gonna see what type of person I truly was. Where my heart was. This Thug Life stuff, it was just ignorance. My intentions was always in the right place. I never killed anybody, I never raped anybody, I never committed no crimes that weren’t honorable-that weren’t to defend myself. So that’s what I’m going to show them. I’m going to show people my true intentions, and my true heart. I’m going to show them the man that my mother raised. I’m going to make them all proud.

In the last year of his life, Pac famously rapped that the gratification of revenge was a close second to sex. Exiting Clinton Correctional Facility, Pac was craving both after a year of fixating. He was newly on the most feared record label of all times (who paid the financially strapped rapper’s seven figure bail). Hungry to be that “boss playa,” he was immediately indoctrinated into the M.O.B. mentality. Pac was put on a pedestal in a new universe where tribe honor was life (or death). This was a 180 for the man who believed those who orchestrated his robbery-shooting were tied to his sexual accusers (as he told Sanyika at 12:00), and that members of his circle were—in his words: disloyal cowards. Pac may have read Maya and made connections with people different than him, but he was still a young man with physical and symbolic wounds that had not fully healed. He said that a fellow inmate told him “I have no friends.” Inside, he adopted that notion. In the last 11 months of his life on the outside, it’s hard to truly say who, if any, Pac truly considered a friend. However, he defined what that expectation entailed in a song released after his death which ties closely to the messaging of his prison letters: “I’m down for you, so ride with me / My enemy’s your enemy / ‘Cause you ain’t ever had a friend like me.” Tupac demanded a partner in his calculated wrath. History suggests that he found it, in his departure from prison.

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Tupac was dead set on speaking his truths, and satisfying his obsession to even all scores. “Listen to what [all rappers are] saying. Don’t just ‘bob ya head to the beat,’ peep the game and listen to what I am saying, and hold us accountable for it. And really…if somebody else blows up and I fade out, that’s just how it’s supposed to be. That’s fate, and I ain’t got no problems with that. I don’t got no problems with no one in the whole industry. I wish everybody success. It’s enough loot for us all to make money,” Tupac said a month away from his release. “But I will say…I already took five bullets, and if I can help it, I don’t plan on taking no more. I would tell each and every person out there [to] forget about that ‘cliquing up thing.’ Be to yourself. Stay to yourself. Trust nobody! Trust no body! Straight up… my closet friend did me in. My closest friends…my homies…people I done took care of their whole family. I done took care of everything for them. Looked out for them. Put them in the game… everything! Turned on me. Fear is stronger than love. Remember that! Fear is stronger than love. All the love I gave… didn’t mean nothing when it came to fear. So it’s all good but I’ma soldier. I always survive. I’ll constantly come back. Only thing that can kill me… is death. That’s the only thing that can stop me is death—and even then—my music will live forever.”

Upon his October 1995 exit, Machiavelli’s wisdom appeared to be louder in Tupac’s mind than Maya Angelou’s. He wanted to do right, heal the hood, and channel that multi-talented artist he’d been earlier. However, the temptation of wrath and revenge (perhaps the real “Thug Passion” cocktail) proved too alluring. From that day forward, when Pac went on the offensive, he seemed to be scrapping with all the oppressors of his life, at once. Tragically, his “eyez” never saw the consequences.