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How Tupac and Biggie Went from Friends to Deadly Rivals

Ben Westhoff

Tupac declined Biggie's offer to manage his career. "Nah, stay with Puff," he told Biggie. "He will make you a star."

Image by Lia Kantrowitz

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Image byLia Kantrowitz for VICE.

The following is excerpted from Original Gangstas: The Untold Story of Dr. Dre, Eazy-E, Ice Cube, Tupac Shakur, and the Birth of West Coast Rap by Ben Westhoff, forthcoming from Hachette Book Group on September 13, the 20th anniversary of Tupac Shakur's death.

Tupac and Biggie first encountered each other in 1993, in Los Angeles. There on business, the Brooklyn-bred rapper Biggie asked a local drug dealer to introduce him to Tupac, who invited Biggie and his party to his house. There, he shared with them a "big freezer bag of the greenest vegetables I'd ever seen," said an intern for Biggie's label, named Dan Smalls, who was part of the group.

Tupac got them high and pulled out a "green army bag" filled with handguns and machine guns. "So now, here we are, in this backyard running around with guns, just playing," continued Dan Smalls in The Fader. "Luckily they were all unloaded. While we were running around, 'Pac walks into the kitchen and starts cooking for us. He's in the kitchen cooking some steaks. We were drinking and smoking and all of a sudden 'Pac was like, 'Yo, come get it.' And we go into the kitchen and he had steaks, and French fries, and bread, and Kool‑Aid and we just sittin' there eating and drinking and laughing. And you know, that's truly where Big and 'Pac's friendship started."

"We all thought he was a dope rapper," Tupac's longtime friend EDI Mean, a member of Tupac's affiliated group the Outlawz, told me. Tupac gifted Biggie a bottle of Hennessy. Biggie slept on Tupac's couch whenever he came back to California, and when Tupac was in New York, he came by Biggie's neighborhood, picking him up in a white limousine and throwing dice with the locals. The pair freestyled back-to-back at a concert called Budweiser Superfest at Madison Square Garden in 1993, with Biggie wowing the crowds with lines like, "Oh my God I'm dropping shit like a pigeon / I hope you're listenin' / Smackin' babies at their christenin'."

Despite the Garden cameo, Biggie still wasn't much known outside of Brooklyn. Tupac, by then a platinum‑selling rapper and movie star, acted as a mentor. Biggie and other young rappers assembled in recording studios or hotel rooms to hear Tupac lecture about how to make it in the game. "'Pac could get up and get to teaching," said EDI Mean. "Everyone was transfixed on this dynamic individual, and soaking up all the information we could soak up." But Tupac devoted special attention to Biggie, grooming him and letting him perform at his concerts. Biggie even told him he'd like to be a part of another of his affiliated groups, called Thug Life. "I trained the nigga, he used to be under me like my lieutenant," Tupac said.

Tupac claimed to have directly influenced Biggie's style. "I used to tell the nigga, 'If you want to make your money, you have to rap for the bitches. Do not rap for the niggas,' " he said. "The bitches will buy your records, and the niggas want what the bitches want." As proof that Biggie had heeded his advice, Tupac cited the difference between his early track, the aggressive "Party and Bullshit," and softer songs from his debut Ready to Die like "Big Poppa," which appealed more to the ladies: "Soon as he buy that wine, I just creep up from behind / And ask what your interests are, who you be with?"

But before Ready to Die came out, Biggie worried he could miss his shot, considering that the new label he was signed to, Bad Boy—owned by his manager Sean "Puffy" Combs—hadn't taken off yet. Things weren't happening for him quickly enough, he complained. He asked Tupac to take over as his manager, in hopes Tupac could advance his music and film career as rapidly as he'd done his own. "Biggie looked like he was wearing the same pair of Timberlands for a year, [while] 'Pac was staying at the Waldorf‑Astoria and buying Rolexes and dating Madonna," EDI Mean said.

But Tupac declined the offer. "Nah, stay with Puff," he told Biggie. "He will make you a star."



In New York to shoot the 1994 film Above the Rim, Tupac became enmeshed with a group of notorious Queens toughs. He was modeling his character Birdie—a gangster involved in youth basketball programs—on a Haiti-born high roller called Jacques "Haitian Jack" Agnant.

Tupac had noticed Haitian Jack at a Manhattan club, surrounded by women and champagne, and asked for an introduction. They also spent time at a Queens bar, where Jack would bring through celebrities including Madonna, Shabba Ranks, and Jamaican musician Buju Banton. (Tupac briefly dated Madonna, after Rosie Perez introduced them at the 1993 Soul Train Awards in LA.) Biggie, who ran in the same circles as Haitian Jack and his associates, warned Tupac to keep his distance from him, to no avail. Tupac liked Jack's swagger. He introduced the rapper to high-end jewelry and Versace duds, as well as the local gangstas who called the shots. "[H]e loved the respect and recognition I got in New York, and I think he wanted that same respect," Haitian Jack said.

The two were partying at a Manhattan club called Nell's in November 1993, where Tupac met a 19-year-old woman named Ayanna Jackson. They got close on the dance floor and went back to his suite at the Le Parker Meridien Hotel. Four days later ,she met up with him at the hotel again, only to encounter not just Tupac, but Haitian Jack, Tupac's road manager Charles "Man Man" Fuller, and another man who was not identified. There, she alleged, the group gang-raped her and forced her to perform oral sex. Tupac claimed he left the bedroom when the other men entered and fell asleep. She called the police, and Tupac, Haitian Jack, and Fuller were arrested. The police also found guns, which Tupac later claimed belonged to Biggie.

The prosecution alleged Tupac, charged with sexual abuse, sodomy, and illegal weapons possession, had offered up Jackson "as a reward for his boys." Tupac denied this, but after the trial told Vibe he blamed himself for "doing nothing" to protect Jackson from the other men. Before the trial began, Tupac's and Fuller's cases were severed from Haitian Jack's; in a deal that Tupac and his lawyer deemed too good to be true, Jack pleaded guilty to two misdemeanors and avoided jail time. Believing Haitian Jack was a snitch, Tupac told a New York Daily News reporter that Jack had set him up. (Ayanna Jackson and Haitian Jack have denied this.)

Calling out a reputed gangster in the press is not sensible. But, ironically, after spending so much time with Jack and his ilk, Tupac had begun to feel invincible. He went wherever he wanted, wearing flashy jewelry worth thousands of dollars. Secure in his street credentials, he was convinced that nobody would mess with him.

Supporting his extended family and paying lawyers for his interminable string of court cases, Tupac's bank accounts withered. In late 1994, he agreed to record a guest verse for a rapper named Little Shawn, who was close with Puffy and Biggie. The invitation came from Little Shawn's manager, Jimmy "Henchman" Rosemond, whom Tupac had met through Haitian Jack, and Tupac was to be paid $7,000.

Tupac had begun to feel invincible.



On November 30, 1994, Tupac arrived stoned to Quad Recording Studios in Times Square. He came with three associates, none of whom were bodyguards, and encountered three other men he didn't know, wearing army fatigues. This was fashion from Brooklyn—Biggie's home—so Tupac assumed they were with him. He felt better about the situation when Biggie's affiliated rapper Lil' Cease yelled down to him that Biggie was upstairs recording. Puffy was there, too.

But before Tupac's crew could get on the elevator, the men in army fatigues drew 9mm guns and ordered them to the floor. Instead, Tupac reached for his own gun. He was shot, beaten, and robbed of his jewelry. He played dead, and the assailants left, at which time he staggered into the elevator and rode it upstairs. When the doors opened, he saw a group including Puffy, Biggie, and Henchman. Tupac said the crew looked surprised and guilty, but Puffy claimed they showed him "nothing but love and concern."

Tupac believed the incident was more than a random heist. "It was like they were mad at me," he said. He claimed to have taken five bullets, including shots to the head and through his scrotum, though forensic evidence suggested he likely shot himself.

Bill Courtney, a retired NYPD cop who also worked hip-hop cases, believed the stick-up was a response to Tupac's Daily News comments against Haitian Jack. "A message was being sent to him not to name-drop," he said.

"Nobody came to rob you," Henchman told Vibe in 2005. "They came to discipline you."

Puffy and Biggie denied their involvement in the crime, or any prior knowledge of it. Haitian Jack also claimed he wasn't involved, and following a separate conviction was deported to Haiti in 2007.


On December 1, 1994, Tupac arrived to a New York City courtroom wearing bandages and confined to a wheelchair, and was pronounced guilty of sexual abuse in the Ayanna Jackson case, though acquitted on the sodomy and weapons charges. Sentenced to a minimum of a year and a half in prison, pending appeal, his bail was set at $3 million.

Unable to raise bail, Tupac served most of his time at Clinton Correctional Facility, a maximum-security prison in upstate New York. Me Against the World, Tupac's third album, was released soon after his prison sentence began. Tupac considered making it his swan song; he was tired of all of the music industry drama. But his passion reignited after a disturbing rumor began to sink in, one that came from people he trusted: that Biggie knew in advance about the Quad studios shooting.

"He owed me more than to turn his head and act like he didn't know niggas was about to blow my fucking head off," he said later. And even if Biggie hadn't set him up, he should at least have been able to find out who did it. "You don't know who shot me in your hometown, these niggas from your neighborhood?"

The way Tupac saw it, his own friend had betrayed him—a friend whom Tupac had helped to acquire fame and fortune.


While in prison, Tupac asked his wife Keisha Morris (whom he had married while incarcerated) to relay a message to Suge Knight, the head of the volatile label Death Row Records: He was broke and needed help. On top of the lawyers' fees and everything else, his mother was losing her house.

"Suge sent $15,000 and put it on his books," Reggie Wright Jr., Death Row's head of security, told me. Tupac was jubilant and sent Suge another message, that he'd like to see him.

Few places in the US were farther away from Los Angeles than Dannemora, New York, where Tupac was incarcerated, but Suge began coming out. Further, Death Row offered him something no one else seemed to be able to deliver: release. Death Row's lawyer David Kenner pledged to help Tupac with his case and began working to spring him on an appeal bond.

Suge didn't just try to recruit Tupac to his label, he offered him a place in his family, the most powerful and out-of-control family in hip-hop.


Tupac was still incarcerated in August 1995, when Suge came to visit him again. Immediately afterward Suge headed down to New York City, where, on August 3, the annual awards show put on by hip-hop magazine the Source was held at Madison Square Garden's Paramount Theater. Death Row spent some $100,000 on its opening-act stage show, which included life-size jail cell replicas.

With his chest puffed out, Suge took the stage to accept his label's award for best soundtrack, for Above the Rim. Giving a stink eye to the audience, he digressed, throwing a pointed barb at Sean "Puffy" Combs, the head of Bad Boy, Biggie Smalls's label. Alluding to Puffy's tendency to insert himself in his performers' works, Suge said: "Any artist out there wanna be an artist, and wanna stay a star, and don't have to worry about the executive producer trying to be all in the videos, all on the records, dancing—come to Death Row."

The venue erupted in boos. Why would you do that? Death Row rapper Nate Dogg thought to himself.

What inspired Suge's bizarre attack? After all, he and Puffy had been cool with each other until fairly recently. They'd discussed how to keep the feds from tracking them, and, earlier in 1995, Suge had even invited Biggie Smalls to perform at his Club 662 in Las Vegas. The show never went off, but this didn't sour their relationship.

What soured it was Tupac.

Suge had flown straight to the Source Awards from visiting Tupac in prison. That's where Tupac not only agreed to join Death Row, but where he told Suge about his anger at Biggie. "I need you to ride with me because I'm going to destroy Bad Boy Records. I believe they had something to do with me getting shot," Tupac told Suge, according to Reggie Wright Jr. Suge pledged his loyalty. Tupac's enemies would be his enemies.

Battle lines had been drawn, and the Source Awards were the first shots in what would become known as the East Coast-West Coast hip-hop wars. Though there's no evidence that Biggie or Puffy knew about Tupac's shooting in advance, Tupac's belief that this was the case—and his ability to convince Suge as much—spurred a conflict that would eventually claim the lives of both Tupac and Biggie. Their murders remain unsolved.

Follow Ben Westhoff on Twitter.

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