Tupac Shakur

Courtesy the recipient

“WHEN WILL YOU LEARN THAT HONESTY CAN NEVER HURT ME.” 

17-YEAR-OLD TUPAC SHAKUR EXPERIENCES A RARE MOMENT OF ROMANTIC ANXIETY

Offering further insight into two (2) earlier letters written to sweetheart Cosima (see lots 102 — in which Tupac admits to falling in love with Cosima, and 103 —in which Tupac expresses desire to define their romantic relationship, both sold in Sotheby's 2022 Hip Hop sale) —this letter uncovers an intervening moment of boyish insecurity. “I think we have both rushed things immensely,” Tupac begins. Desperate to retract his earnest declaration of love, Tupac's recurring anxiety around being rejected due to the strength of his feelings rears its head. Claiming that this lovestruck proclamation was simply the result of getting “caught up in the ‘whirlwind,'” Tupac insists that he “just let loose before it was time.” It’s not that Tupac doesn’t love “the beautiful and caring” Cosima, but that he’d rather “give [their] relationship as FRIENDS a chance to survive” than allow it to succumb to the pressure of a romance that might not work out. This is that typical push-and-pull that has characterized teenage relationships for decades and even Tupac, often wise beyond his years, is not immune. “This is not goodbye,” he vows in conclusion, “and maybe in the future I can be lucky enough 2 have you.”

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 71-74 and 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.