Offered in this lot is a handwritten poem written by the legendary rapper Tupac Shakur while the young musician was incarcerated at Clinton Correctional Facility in August of 1995. The letter, addressed to a woman named “Simi”, highlights Shakur’s insecurities while imprisoned, with the rapper writing “Can I convince your doubting heart / 2 trust itself 2 me? / How can I hold your hands and kiss u softly / Without making you fear me?” The poem is titled “How Can I”, with the “I” stylized as a sketch of a person’s eye by Shakur. Near the top of the poem, Shakur wrote “Exclusively 4 Simi, from Tupac Shakur”. At the bottom, Shakur signed the poem “Thinkin’ of U / 2Pac!”. The poem is in excellent condition. It is handwritten in blue pen on a piece of lined paper. “Aug 25, 1995 / 7:00pm” is handwritten in red pen, as well as the “4 Simi” line. This historic poem is a unique relic from the short but influential career of the American treasure Tupac Shakur. It comes with a LOA from JSA.

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