Tupac Shakur
Sexual assault case, prison sentence, appeal and release

In November 1993, Shakur and two other men were charged in New York with sodomizing a woman in Shakur's hotel room. The woman, Ayanna Jackson, alleged that after she performed oral sex on Shakur at the public dance floor of a Manhattan nightclub, she went to his hotel room on a later day, when Shakur, record executive Jacques "Haitian Jack" Agnant, Shakur's road manager Charles Fuller and an unidentified fourth man apprehended and forced her to perform non-consensual oral sex on each of them. Shakur was also charged with illegal possession of a firearm as two guns were found in the hotel room. Interviewed on The Arsenio Hall Show, Shakur said he was hurt that "a woman would accuse me of taking something from her", as he had been raised in a female household and surrounded by women his whole life.

On December 1, 1994, Shakur was acquitted of three counts of sodomy and the associated gun charges, but convicted of two counts of first-degree sexual abuse for "forcibly touching the woman's buttocks" in his hotel room. Jurors have said the lack of evidence stymied a sodomy conviction. Shakur's lawyer characterized the sentence as "out of line" with the groping conviction and the setting of bail at $3 million as "inhumane". Shakur's accuser later filed a civil suit against Shakur seeking $10 million for punitive damages which was subsequently settled.

After Shakur had been convicted of sexual abuse, Jacques Agnant's case was separated and closed via misdemeanor plea without incarceration. A. J. Benza reported in New York Daily News Shakur's new disdain for Agnant who Shakur theorized had set him up with the case. Shakur reportedly believed his accuser was connected to and had sexual relations with Agnant and James "Henchman" Rosemond, who he considered to be behind the 1994 Quad Studios shooting.

Shakur was unable to post the $3 million bond to keep himself free until sentencing so he surrendered himself to authorities at the Bellevue Hospital Jail Ward in New York City on December 23, 1994. At the time, he was still recovering from injuries he received on November 30, when he was shot five times and robbed at Quad Studios. In January 1995, Shakur was moved to the North Infirmary Command (NIC) on Rikers Island in the Bronx. On February 7, 1995, he was sentenced to 18 months to 4 + 1 ⁄ 2 years in prison by a judge who decried "an act of brutal violence against a helpless woman".

In March 1995, Shakur was transferred to Clinton Correctional Facility in Dannemora. While imprisoned, he began reading again, which he had been unable to do as his career progressed due to his marijuana and alcohol habits. Works such as The Prince by Italian philosopher Niccolò Machiavelli and The Art of War by Chinese military strategist Sun Tzu sparked Shakur's interest in philosophy, philosophy of war and military strategy. On April 29, 1995, Shakur married his girlfriend Keisha Morris; the marriage was later annulled. While in prison, Shakur exchanged letters with celebrities such as Jim Carrey and Tony Danza among others. He was also visited by Al Sharpton, who helped Shakur get released from solitary confinement.

By October 1995, pending judicial appeal, Shakur was incarcerated in New York. On October 12, he bonded out of the maximum security Dannemora Clinton Correctional Facility in the process of appealing his conviction, once Suge Knight, CEO of Death Row Records, arraigned for posting of his $1.4 million bond.
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