Tupac Shakur

Courtesy the recipient

“P.S. I HOPE U DON’T HATE ME AND U UNDERSTAND MY FEELINGS.”

17-YEAR-OLD TUPAC SHAKUR EXTENDS AN OLIVE BRANCH

Penned following a heated disagreement between himself and Cosima at a Talampais High School dance, the present two-page letter is Tupac’s reaction to this proto-lover’s spat and his attempt to redefine the relationship accordingly. “I don’t know how 2 say what I need to say without being mean or unsensitive,” Tupac opens earnestly, pushing past his hesitation to continue, “[h]owever it would be better 4 me if I put some space between u and I.” While he cannot and does not want to deny his attraction to Cosima, “4 some reason I don’t think u and I can be friends.” Clearly conflicted about how to proceed, Tupac quickly reworks that thought, stating, “I do like u but the only ^ ^thing I want from u is friendship. I don’t care how impossible that sounds, this is my intention.” Sharing the internal processes that lead to the argument, he advances, “I feel as though u give more respect 2 those that disrespect u. On the other hand, I have never disrespected u nor have I let anyone disrespect u in my presence.” Tupac effortlessly explains the depth his feelings on the page in a way he was unable to face to face, demonstrating what would become his lifelong ease with the written word. He insists—smarting from her rejection of his intended gallantry—his only goal in pulling Cosima aside that night was to caution her against fellow students with less pure intentions than his own. While later letters (see lot 101 in 2022 Hip Hop sale) see the pair comfortably settled into a casual dynamic defined by the elder Tupac regularly advising the younger Cosima on the ways of teenage dating, they are not yet there.

Here, with adolescent egos flaring, the young lovers are figuring out how to balance possession and devotion in real time. Tupac writes, “I wasn’t trying 2 be your father, only a friend.” Displaying an emotional maturity that exceeds his 17 years, he closes the letter, “I apologize for crowding u and I wish u sucess [sic].” Then—because he is still a lovestruck teen after all—Tupac dashes out a quick postscript, “P.S. I hope u don’t hate me and u understand my feelings.”

In the summer of 1988, 17-year-old Tupac Shakur and family moved from Baltimore to Marin City, California. There, Tupac attended Tamalpais High School in nearby Mill Valley, where he poured his creative energies into the award-winning, student-run Ensemble Theatre Company, and perhaps most importantly, The Microphone Sessions, a poetry workshop run by Leila Steinberg. Steinberg quickly recognized the future superstar's talent, and took him under her wing, mentoring his progress as a writer, and even welcoming Tupac into her family's home for a time. Their relationship would prove to be pivotal for Tupac's career—not only did Steinberg help Tupac hone his writing skills, but she would also become his first manager, organizing a concert for his rap group Strictly Dope, with whom Tupac recorded under the stage name MC New York. Steinberg helped broker Tupac's signing with Atron Gregory, manager of Digital Underground, and in 1990, Tupac joined the group as a roadie and back-up dancer, before going on to debut with them in 1991, under the stage name 2Pac. The rest is history.

Cosima, the recipient of the present letter, was a Sophomore and fellow member of the Ensemble Theatre Company at Tamalpais High. The pair shared a profound connection at this time, just before and in the beginning stages of Tupac's rise to fame, from their first meeting on Cosima's birthday in October 1988, and lasting for approximately 7-8 months. This, and the other letters offered (see lots 71, and 73-76) reveal a tender-hearted, fiercely passionate young man, dedicated to clear communication who loved people deeply, and expressed emotions without fear. Tupac’s ability to love so deeply, and to plainly express this love continues to explain the indelible mark he left on the hearts of those who knew him and devotees around the globe. These letters capture Tupac at a seminal juncture—an adolescent on the edge of true maturity, a natural wordsmith evolving into a lyricist and poet.