Tupac at the Crossroads

Fifteen years after Tupac Shakur's murder, we examine some key turning points in Makaveli's life and death.

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Image via Complex Original
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Intro

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Afeni

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Afeni's Acquittal

Date: May 13, 1971

Trajectory: The Journey Begins

Choice or Circumstance: Circumstance

Complex says: Alice Faye Williams, born in North Carolina in 1947 and raised in New York City, became politicized by the Black Power movement of the 1960s and renamed herself Afeni. She joined the Black Panther Party and married one of its leaders, Lumumba Shakur. In 1969, she and 20 others were swept up in a NYPD raid. Afeni Shakur was among 13 of the “New York 21” charged collectively with over 100 counts of conspiracy to attack government buildings and murder officials.

Released on bail in 1970, she got pregnant while awaiting trial. After several of her codefendants jumped bail, she and her unborn son were thrown back into prison until the trial was finished. If Afeni Shakur had not been acquitted of all charges, her child may very well have been born behind bars and taken from her. As it was, Tupac Amaru Shakur emerged from the womb into freedom on June 16, 1971, in Harlem.

Baltimore Bound

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Baltimore Bound

Date: 1984

Trajectory: U Turn

Choice or Circumstance: Circumstance

Complex says: Determined to turn her life around and give her children—Tupac and his younger sister Sekyiwa—a fighting chance, Afeni Shakur moved her family to Baltimore, Maryland, where she took computer-training courses and eventually enrolled young Tupac in the prestigious Baltimore School for the Arts.

Though Tupac had already caught the performance bug in New York — where he acted in the 125th Street Repertory Ensemble’s production of “Raisin In The Sun” — Tupac’s experience at BSA put him on the path to becoming a multitalented, multidimensional artist, and widened his cultural horizons and social circle (including the beginning of a lifelong friendship with Jada Pinkett).

Marin

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Move to Marin

Date: 1988

Trajectory: Westward

Choice or Circumstance: Circumstance

Complex says: In an abusive relationship and without adequate means to support her kids, Afeni Shakur packed off 17-year-old Tupac and his younger sister to live with a friend in the San Francisco suburb of Marin City. But Tupac’s new home was in actuality a suburban ghetto—a pocket of poverty surrounded by the homes of the wealthy—and his guardian was an alcoholic.

By the time Afeni arrived to join her children, Tupac’s recently expanded horizons had narrowed again. Afeni became addicted to crack cocaine and Tupac bunked with young friends, a student and budding poet forced to decipher the code of the streets.

Though the move to the Bay Area deprived Tupac of his graduation from performing arts school, it was Marin that focused Tupac’s talents for poetry and performance into a quest to become a hip-hop MC.

Meeting Mentors

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Meeting Mentors

Date: 1989

Trajectory: Getting directions

Choice or Circumstance: Choice

The Choice: Art over aimlessness

Complex says: Leila Steinberg, a young activist and party promoter in Marin, met Tupac Shakur and became convinced that he could be a star. She let Tupac board with her family, helped him cultivate himself as a poet and lyricist through her writing workshops, and became his manager.

Fatefully, Steinberg took Shakur’s video demo (really just a tape of him rapping in her front yard) to a Bay Area-based artist manager named Atron Gregory, whose group Digital Underground had just started to break big.

Gregory liked what he saw. Signing Shakur to his production company, TNT Records, he and Steinberg became Shakur’s co-managers. Leila Steinberg was the first person to take Shakur seriously as a hip-hop artist, while Atron Gregory gave Tupac access to the music industry.

Down With The Underground

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Down With The Underground

Date: 1990

Trajectory: All around the world

Choice or Circumstance: Choice

The Choice: Chasing the dream over dreaming the dream

Complex says: Atron Gregory would not have signed Tupac Shakur without the blessing of TNT’s main producer, Shock G, the leader of Digital Underground. And it was Shock who enabled Shakur to come out on a national tour with the group as a dancer and occasional backup MC.

Shakur’s relationship with the group was rocky — his volatility got him fired and rehired a few times. But Shock G respected him enough to let him kick a verse on “Same Song,” the lead single from Digital Underground’s follow-up album. And just like that, Tupac Shakur — branding himself as “2Pac” — made his first appearance on record, cosigned by one of the most popular and respected groups of the day.

Interscope

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Signing To Interscope

Date: 1991

Trajectory: To the top

Choice or Circumstance: Choice

The Choice: Risky creative career over a safe bet

Complex says: Despite Tupac’s cameo with Digital Underground, Atron Gregory found no interest in him at the record labels that specialized in hip-hop. Out of money and pressed for time, Tupac received an offer to run a New Black Panther youth program in Atlanta, and almost left his hip-hop aspirations behind.

Finally, Tupac’s demo made its way to an A&R executive named Tom Whalley at a start-up record label called Interscope. Whalley liked what he heard, and when he met Tupac in person, liked what he saw. (“Have you ever seen eyes like that?" Whalley was reported to have said of Tupac’s “presence”).

Whalley passed the demo to label founder Ted Field, who told Whalley that he believed Tupac had “the most original voice” he’d ever heard. Interscope Records, a label that had until then only released the pop rap of Markey Mark and Gerardo, gave “2Pac” a record deal, launching his career in earnest.

Tupac vs. The Cops

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Tupac vs. The Cops

Date: October 1991

Trajectory: Across the street, against the law

Choice or Circumstance: Choice

The Choice: Challenging the system over knuckling under to it

Complex says: Just one month before the release of his first album, 2Pacalypse Now, Tupac was arrested by police in Oakland, California for jaywalking. Born into an extended family that had been persecuted by police, Shakur maintained an attitude of complete contempt for cops into his adulthood. Shakur protested, and the police beat him.


 

When Shakur and the police met, Shakur almost always won, adding luster to his revolutionary pedigree.

 

Shakur sued them for $10 million, and they settled for $42,000. It was, on one hand, the first of many high profile run-ins with the law. On the other hand, when Shakur and the police met, Shakur almost always won, adding luster to his revolutionary pedigree.

In 1993, a civil suit against Interscope’s parent Time Warner — claiming that songs from 2Pacalypse Now, provoked a gang member to shoot a Texas policeman — proved unsuccessful. Later that year, Tupac was exonerated in a shootout with two off-duty Atlanta cops who turned out to be drunk and brandishing a pilfered gun.

Juice

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Becoming Bishop

Date: January 1992

Trajectory: To Hollywood

Choice or Circumstance: Choice

The Choice: Immersion in his persona over separation from it

Complex says: Before Tupac Shakur had even released his first record, he was cast in a leading role in a major motion picture. It was, like so many moments in Tupac’s life, the result of serendipity. Tupac had tagged along on Digital Underground bandmate Money B’s audition for a role in a movie entitled Juice. After Money B underwhelmed the producers, Tupac grabbed the script and seized the role of “Bishop,” a street kid with good intentions who unravels throughout the story into a traitorous murderer.


 

Tupac Shakur got his first introduction to mainstream American audiences—not as a rapper, but as an actor.

 

In early 1992, Tupac Shakur got his first introduction to mainstream American audiences—not as a rapper, but as an actor. Undoubtedly Tupac’s performing arts schooling served him well—his debut performance was lauded by critics. But part of Tupac’s success in the role was the personal experiences he brought to it.

His character Bishop’s descent into depravity and the code of the street mirrored Tupac’s own journey from acting student to wannabe gangbanger; and Bishop’s death wish would later seem to presage Tupac’s own.

Getting Around

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Getting Around

Date: 1993

Trajectory: To the top of the charts

Choice or Circumstance: Choice

The Choice: Popular anthems over narcissistic elegies

Complex says: The irony of Tupac’s lightning-fast jump to the silver screen was that none of his songs had yet been huge hits. One full year after the release of Juice, Tupac had yet to crack the top 20 on the pop and R&B singles charts. In 1993, with the release of his second album, Strictly 4 My N.I.G.G.A.Z., that would all change.

“I Get Around” was originally meant as a Digital Underground track—it certainly sounded like one with full verses from Shock G. and Money B. But recorded as it was during a dispute with the group’s label Tommy Boy Records, it became a 2Pac single instead, and his first hit, peaking at No. 5 on the R&B chart, No. 11 pop. “I Get Around” was followed by the similarly successful “Keep Ya Head Up,” which established 2Pac as a hitmaker, and cemented his image in the hip-hop community as an artist of lyrical depth and political purpose.

Biggie

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Meeting Biggie

Date: 1993

Trajectory: To the east, my brother

Choice or Circumstance: Choice

The Choice: Connection over isolation

Complex says: Tupac Shakur was already a hip-hop star when he first heard “Party & Bullshit,” the debut single from an obscure Brooklyn rapper named Biggie Smalls (soon to be rechristened “The Notorious B.I.G.”) Shakur obsessed over the song. He and Big eventually met, and the two became fast friends, hanging while on the road and whenever Shakur’s travels took him to New York.


 

Tupac and Biggie freestyled together in two legendary performances at New York’s Palladium and Madison Square Garden.

 

Tupac and Biggie freestyled together in two legendary performances at New York’s Palladium and Madison Square Garden. They were a classic case of opposites attracting — beautiful Tupac, the West Coast rapper who emerged from neglect and poverty to become a poet and actor; and homely Big, the East Coast MC who came from a comfortable, loving home to become a drug dealer and street scientist. Tupac had the fame and lifestyle that Big coveted; Big had the street smarts and experience that Tupac lacked.

A year later, Tupac would turn on his friend in the most public fashion, and the rift in their casual friendship — exploited in a rivalry between their business benefactors — would soon take on historic, tragic significance.

Haitian Jack

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Bad Company

Date: 1994

Trajectory: Into the wrong crowd

Choice or Circumstance: Choice

The Choice: Courting the approval of others over developing his own self-esteem

Complex says: When Tupac Shakur was cast in the movie Above The Rim for the role of a drug dealer named “Birdie,” it triggered long-simmering insecurities about his street pedigree. In order to play an East Coast “baller,” Tupac wanted to study men whom he felt played that role in real life.


 

It can be argued that Shakur’s choices—to associate with and subsequently alienate these two men—ruined his life.

 

Shakur was introduced to a man name Jacques Agnant, known on the streets and in the industry as “Haitian Jack.” Shakur and Agnant became friendly, and Agnant reportedly promised Shakur that he would “hold him down” in New York. In his travels, Shakur also met an artist manager named Jimmy “Henchmen” Rosemond, who also had a fearsome reputation among music business denizens.

While neither Agnant or Rosemond ever harmed Shakur directly, it can be argued that Shakur’s choices—to associate with and subsequently alienate these two men—ruined his life. For Agnant and Rosemond would be suspected and implicated (though never proven culpable) in two respective incidents of vice and violence from which Tupac Shakur would never recover.

Rape Case

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Catching The Rape Case

Date: November 1993

Trajectory: Back to the hotel

Choice or Circumstance: Choice

The Choice: Protecting the powerful over defending the powerless

Complex says: On November 14, 1993, Tupac Shakur accompanied Agnant to a Manhattan nightclub called Nell’s. There, one of Agnant’s associates introduced Tupac to 19-year-old Ayanna Jackson. After arousing each other on the dance floor, Jackson went with Shakur to his suite at the Parker Meridian hotel and had sex.

Four days later, Tupac invited her back to the hotel. This time, however, they were not alone: Agnant and several others were present. Jackson would emerge from the suite hours later, telling hotel security and police that she had been gang raped by Shakur, Agnant and their alleged accomplices. Shakur was arrested and charged with sexual abuse, sodomy, and illegal possession of a firearm. If convicted, he faced a potentially career-killing prison sentence.

Quad Shooting

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The Quad Shooting

Date: November 29, 1994

Trajectory: I.C.U.

Choice or Circumstance: Circumstance

Complex says: On the eve of final arguments in Tupac Shakur’s rap case, a manager of rapper Little Shawn invited Shakur to Quad Recording Studios in Manhattan on the promise of $7,000 for a cameo verse. Hours later, when Shakur arrived with his entourage in the Quad lobby, they were greeted by two armed men, who demanded that Shakur remove his jewels. Tupac resisted, convinced that these men meant not to rob him but kill him. The assailants pumped five shots into Tupac’s body, beat him, and stole his valuables before running out into the street.

Minutes later, when a dazed and bleeding Tupac arrived in the studios upstairs, he saw people he knew—Big’s producer Puffy, Little Shawn, and his manager Jimmy Rosemond—and, to his mind, none of them seemed to notice or care. When the assembled luminaries finally saw Tupac’s injuries, they quickly attended to him, and Tupac was rushed to the hospital. But for Tupac, the damage was as much psychological as physical, and paranoia began to set in. Tupac was convinced that he had been set up by some of the men in that room.

Conviction And Sentencing

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Conviction And Sentencing

Date: December 1, 1994 & February 8, 1995

Trajectory: To prison

Choice or Circumstance: Circumstance

Complex says: In a wheelchair still recovering from his shooting and subsequent surgery a few days before, Tupac Shakur sat in the courtroom of Judge Daniel P. Fitzgerald to hear the jury’s verdict. He was found guilty of sexual abuse, and later sentenced to 1 1/2 to 4/ 1/2 years in prison.

Tupac Shakur, the young man who wrote paeans to Black women like “Brenda’s Got A Baby,” “Dear Mama” and “Keep Ya Head Up,” was a convicted felon. It seemed inexplicable to some, a few of whom felt that Tupac, as a well-known public figure, was taking the fall for some of the other men in that hotel room. His life and career would be on pause until he had served his sentence or found a way to appeal the case.

The Jailhouse Interview

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The Jailhouse Interview

Date: April 1995

Trajectory: To battle stations

Choice or Circumstance: Choice

The Choice: Blame and rage over responsibility and reason

Complex says: While locked up in New York City’s Rikers Island jail awaiting sentencing, Tupac Shakur agreed to be interviewed by journalist Kevin Powell for VIBE magazine. In a rambling conversation, Shakur detailed the night of the Quad Studios shooting, and accused The Notorious B.I.G., Sean “Puffy” Combs, Andre Harrell, and Lil’ Cease of complicity in the attack.

It was a stunning split and public provocation that seemed to confirm the increasing chatter on the scene about the hip-hop “whodunnit,” fed also by the February 1995 release of The Notorious B.I.G.’s song “Who Shot Ya?” Whether or not the Bad Boy actually crew had anything to do with Tupac’s shooting was now beside the point. Tupac had used the VIBE interview to start a war with Bad Boy over the incident.

Suge Knight

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Signing With Suge

Date: Fall 1995

Trajectory: To Death Row

Choice or Circumstance: Choice

The Choice: Fear over courage

Complex says: While Atron Gregory—now co-managing Tupac with Shakur family friend Watani Tyehimba—worked furiously to arrange an appeal and bail package, Tupac languished in the Clinton Correctional Facility in Dannemora, New York, and nursed deepening resentments for his enemies, real and perceived.


 

Shakur had joined a mighty crew, but now he was truly alone; he had aligned himself with the powerful, but given away his own.

 

He and Big had seemingly switched places—Shakur sidelined while Big enjoyed the first waves of his own stardom. It was in Dannemora that Tupac first seriously considered the overtures from CEO Suge Knight to sign his contract over to Death Row Records. It was an awful deal. Tupac was already signed through Gregory’s production deal to Interscope, and a big enough star to renegotiate his own price directly with Interscope. But Gregory understood Interscope head Jimmy Iovine’s reasoning: that the out-of-control Shakur might be better controlled by Knight.

Tupac had his own reasons for jumping now. Death Row was a commercial juggernaut, and by joining he’d also have access to Dr. Dre’s production skills. Knight was offering a sizable advance to the cash-strapped Shakur, and intimating that his lawyer had the power to sway the appeals process. But mostly, Death Row was feared by the people whom Tupac was afraid of. When Tupac made his self-described “deal with the devil” official, Gregory dropped him as a client.

Shakur had joined a mighty crew, but now he was truly alone; he had aligned himself with the powerful, but given away his own. The irony of the switch to Death Row was that Gregory and Tyehimba’s quest for appeal and bail came through just in time to make Suge Knight look like the proverbial knight in shining armor. And Shakur’s alignment with Knight, who was engaged in a similar campaign against Bad Boy and Sean “Puffy” Combs, merged two personal feuds between individual artists and execs into what looked like a full-blown war between the Coasts.

All Eyez On Me

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All Eyez On Me

Date: Late 1995, Early 1996

Trajectory: The studio

Choice or Circumstance: Choice

The Choice: Letting performance spill over into real life

Complex says: On October 12, 1995, Tupac walked out of prison and, almost immediately thereafter, locked himself up again—this time in the recording studio. Prolific at all times, Shakur was much more so during his months in prison. The first Death Row sessions were an outlet for all his pent-up creativity.


 

The title of the hit album was also a metaphor for Shakur’s increasingly hostile grandstanding.

 

The result, released on February 16, 1996, was a double album entitled All Eyez On Me. It would be by far Tupac Shakur’s most successful record of all time, selling over 9 million copies, peaking at No. 1 on the Billboard charts, and yielding classic singles like the Dr. Dre–produced “California Love” and “How Do U Want It.” But the title of the hit album was also a metaphor for Shakur’s increasingly hostile grandstanding.

In March 1996, Puffy, Big and the Bad Boy crew arrived in Los Angeles for the Soul Train Music Awards, where Tupac and Big saw each other in person for the first time since their rift. In the middle of the tense standoff was Tupac, dressed head-to-toe in camouflage, hanging out of the window of a moving car, hurling epithets at the Bad Boy contingent and screaming “Westside!” Big was bemused: “That’s Bishop!” Big recounted. “Whatever he’s doing right now, that’s the role he’s playing. He played that shit to a tee.”

Fraternizing With Faith

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Fraternizing With Faith

Date: 1995-1996

Trajectory: The low road

Choice or Circumstance: Choice

The Choice: Manipulation over honesty

Complex says: Tupac Shakur met Biggie’s estranged wife only after the war of words against his former friend had begun. Her marriage to Big on the rocks, Faith was pleasant to Shakur during their first meeting at a nightclub. She didn’t give a thought to the rift between Tupac and her husband because, according to Faith, the enmity was one-sided—she'd never heard Big utter a bad word about his former friend.


 

The innuendos about Faith were the first time that Shakur got a rise out of Big, who had long since pledged with Puffy to remain silent about Tupac’s accusations.

 

Faith would become an unwitting pawn in an unseemly (and sexist) scheme by Shakur and Suge Knight to humiliate Big, Puffy, and Bad Boy. Tupac invited Faith to Death Row’s recording studio to perform on a song called “Wonda Why They Call U Bitch.”

On another day, according to Evans, he lured her to his hotel room with promise of payment. “If I give it to you,” Evans recalled Tupac saying, “then you gotta be my bitch.” Tupac then demanded oral sex and Faith ran from the room.

Months later, in an interview with the New York Times Magazine, Knight and Shakur intimated that Tupac and Faith had had an affair. Puffy and Big were livid, and Big reportedly came to Faith’s Manhattan hotel room and attacked her for her betrayal, ignoring her claims to the contrary.

The innuendos about Faith were the first time Shakur got a rise out of Big, who had long since pledged with Puffy to remain silent about Tupac’s accusations. After taking out his anger physically on Faith, Big’s response to Tupac was comically lyrical: “If Faye had twins,” he rapped with Jay-Z on “Brooklyn’s Finest,” “she’d prolly have two ’Pacs.”

Shooting

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Scuffle And Shooting

Date: September 7, 1996

Trajectory: To Vegas

Choice or Circumstance: Circumstance

Complex says: It did not take long after Tupac Shakur’s return to life as a free man for him to realize that he'd signed over much of his freedom to Suge Knight. While claiming undying loyalty to Death Row, Shakur was already, by many accounts, distancing himself from the company — firing Death Row’s lawyer, forming his own production company.


 

A gunman emerged, and pumped four shots into Tupac Shakur’s body, one of the bullets grazing Suge Knight’s forehead.

 

It was against this backdrop that Shakur accompanied Knight to the Mike Tyson-Bruce Seldon boxing match at the MGM Grand hotel in Las Vegas. After the brief fight, Shakur and Knight got into one of their own in the lobby with rival gang member Orlando Anderson.

After the incident, Shakur and Knight left the hotel in a black BMW. Stopped in traffic on the Strip, another car pulled up alongside Knight’s. A gunman emerged, and pumped four shots into Tupac Shakur’s body, one of the bullets grazing Suge Knight’s forehead.

Transported to University Medical Center, Shakur would die of his injuries six days later, surrounded by his mother, girlfriend Kidada Jones, and other family and friends. In the wake of the shooting, many assumed that the hotel scuffle with Anderson might have prompted a revenge attack.

Others who knew of Shakur’s unhappiness with Suge Knight saw the shooting as part of a nefarious plot by Knight. Still others assumed that the orders to kill might have come from Puffy, Bad Boy and Big. The case would never be settled, but this much was sure: Tupac Amaru Shakur, the Black Power prince with so much promise, was dead.

Makaveli

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Final Salvos

Date: 1996

Trajectory: To infinity and beyond

Choice or Circumstance: Choice

The Choice: Speaking his mind over holding his tongue

Complex says: Tupac Shakur’s accelerated productivity in the last year of his life meant that he left an enormous body of unreleased work in his wake. Combined with the prophetic nature of Tupac’s lyrics, his superhuman work-ethic seemed to some to be evidence of a supernatural immortality.


 

Combined with the prophetic nature of Tupac’s lyrics, his superhuman work-ethic seemed to be evidence of a supernatural immortality.

 

The last new track released before Tupac’s death, a b-side single called “Hit ‘Em Up,” was an unrelenting, curse-filled barrage against every perceived enemy — first and foremost The Notorious B.I.G. But it was the release rushed out just after Tupac’s death that made fans and foes alike prickle with mystery.

The Don Killuminati (The 7 Day Theory) was not technically a Tupac album, billed as it was to someone called Makaveli. But the artist was most definitely Tupac, and the lyrics so prescient and the presentation so eerie that many wondered whether Tupac had either predicted his own death, or faked it (as Makaveli’s namesake Prince Nicolo Machiavelli once councelled in his book, The Prince).

Old friends like Shock G of Digital Underground would later recount hearing Tupac play these tracks proudly, touting them as “my shit” in opposition to the recordings he was doing to fulfill his obligations to Suge Knight. The Makaveli album stands, perhaps, as Tupac’s greatest creative work, and its success paved the way for many posthumous releases and an perennial presence for the martyred rapper on the airwaves and in the ether.

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