2022 Holiday Auction of Autographs, Memorabilia & Trading Cards - Auction Closes Thurs, Dec 8th
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Incredible handwritten letter in which Tupac discusses his challenges to keep his career going from behind bars and his endeavors reading Machiavelli's "The Prince"--a book which heavily influenced his final studio album!

Tupac Shakur was an international superstar in the 1990s who ranks alongside Dr. Dre, Ice Cube, Snoop Dogg, Nas and The Notorious BIG as one of the most influential hip-hop artists of all time. Rolling Stone named him one of its "100 Greatest Artists of All Time." In the magazine, 50 Cent wrote, "Every rapper who grew up in the Nineties owes something to Tupac. People either try to emulate him in some way, or they go in a different direction because they didn't like what he did. But whatever you think of him, he definitely developed his own style: He didn't sound like anyone who came before him." The Rock and Roll Hall of Fame inducted Tupac in 2017 - the first year in which he was eligible for enshrinement, 21 years after his death.

For much of 1995, Tupac languished in prison, his ascent into global celebrity temporarily put on hiatus. While in prison, one of the only creative outlets for Tupac was writing, something he did both religiously and prolifically. Offered here is a fascinating letter from Tupac, meant for a flame of his named Simi Chouhan, written and sent while Tupac was serving his jail sentence. This letter provides incredible insight into the life and career of one of the greatest hip-hop artists in history. Dated August 25, 1996, the letter reads, in full:

Dearest Simi,

As alwayz your letter (card) brightened my day immensely. It seemz u had quite the scare at your apartment. Please, be careful Simi! This world can be a beautiful place but it also can be a very brutal place so stay paranoid if u must but stay safe. I would truly go crazy if something happened 2 U. So 4 ure sake and mine, stay alert and never let your guardz down. I'm still working for on my bail and keeping my business Str8 as well as reading. I'm just starting to read Machiavelli's The Prince. Anything to escape the glum reality of prison life. Since I can't appear in any of my videos I work constantly on coming up with fresh ideas 2 improve the quality of my music. I just arranged the 3rd video 4 a song called "Temptation". It's very different than any other video. It's a short movie featuring several celebrities (Coolio, Salt N' Pepa, Miss America '93, Ice-T, Cypress Hill, Adina Howard and some others). There is no actual rapping this time just acting and performance. I hope it comes out good. It looked good on paper. A few days after this letter arrives you should receive a Fed-Ex package from me a small token of gratitude 4 your support and kind wordz. You are on my mind alot Simi. The brightness of your smile the glow from your spirit. I feel all of it I am learning how 2 be patient and humble and with that in mind I am looking forward 2 our journey together. I have a request of you. I am going 2 include some tape titles and I would like 4 U 2 get the tapes and when U R alone listen 2 them and think of me. I have them here with me and I want U 2 know what I hear & feel when I think of U maybe you'll feel my vibe. Again, please be careful. Stay safe. Know that U R in my heart and I think of u often. Good luck in all u dream 4. Enjoy yourself but be cautious of the negative!

Passionately,
2Pac

The idea of the Prince appealed to Tupac, who saw himself as both a ruthless figure and one to be admired, and loved, by his subjects. The influence of Machiavelli would loom heavily on Tupac's creativity. In fact, not only was the theme of Machiavelli's philosophies ever present in Tupac's lyrics on his final studio album "The Don Killuminati", but Tupac released the album under the moniker "Makaveli". This letter provides an intriguing glimpse into the dawn of a substantial influence in Tupac's final creative endeavors before his untimely passing.

The letter is accompanied by the original 9.5" x 4" envelope hand addressed by Tupac, with his handwritten name, return address and inmate number. Each piece of this three piece set is accompanied by its own Letter of Authenticity from James Spence Authentication (JSA).

Below is the video for "Temptations", which Tupac discusses in detail in this letter!

Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)
Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading The Prince by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)
Tupac Shakur Handwritten 2-Page Letter with Incredible Content Discussing His Career Behind Bars & Reading "The Prince" by Machiavelli - The Inspiration for Makaveli! (JSA LOAs)
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