Another auction highlight is a deeply personal archive of 22 autographed love letters written by a 16-year-old Tupac Shakur to Kathy Loy, a high school sweetheart and fellow student at the Baltimore School for the Arts (estimate $60/80,000). A total of 42 pages on 24 sheets of paper and one greeting card, the letters are signed by Shakur with a variety of terms of endearment: “Love, Tupac”, “4 Eternity, Tupac”, “With Passion, Tupac", "Forever Yours, Tupac" and "With All My Heart, Tupac". Written when Shakur was enrolled in the 10th grade theater class and Loy was enrolled in the 11th grade theater class, the letters range in date from late March 1987 to April 1988 and chronicle the approximately two-month long romance between the pair – spanning their first meeting, to their eventual break-up, and a letter of regret sent a year later.

The heartfelt and sweetly-sincere correspondence reveals Shakur’s vulnerability and naturally poetic writing-style, with frequent lyrical turns and separate love poems included in the body of the letters, which set the foundation for his distinctive style and tone as a rapper. For example, in one letter he writes "I love you now more than ever, want you now more than before, No one compares to you, the one that I adore...". The letters capture a whirlwind romance between the couple with Shakur promptly professing his love to Loy but then just as quickly experiencing feelings of insecurity and the fear of losing her.

The letters also illustrate Shakur’s close friendship with fellow student Jada Pinkett, who he refers to in one letter writing, “Jada told me she can see how much I love you…’, as well as provide a small glimpse into his home life with mentions of his mother working late nights and his responsibilities to help care for his cousins.

Shakur even writes to Loy about his nascent music career, divulging the future superstar’s doubts about pursuing rap as a profession. He pens "My old manager came over and said she doesn't want me to retire from rap but I think I am because I can't handle too much rejection and I don't have the time....”. Shakur also admits to fearing rejection and his lack of confidence, noting that “I just want to be less sensitive and less of a pest.... What I am feeling has to do with my insecurities, and I have to handle that on my own....”.

In the final letter addressed to ‘Ms. Loy’ and written nearly a year after the pair's break up, Shakur shares that now, at the age of 17, he has moved out of his mother's home and sincerely expresses regret over their break-up while tenderly recalling the good times they spent together writing, "Forgive me while I reminisce....do you remember?".