The crown has been in photographer Barron Claiborne’s possession since he captured Biggie for the cover of Rap Pages magazine. Claiborne had provided the prop, hoping to portray Biggie as the king of New York. Sean “Diddy” Combs, owner of Biggie’s label Bad Boy Entertainment, was with the rapper on the photo shoot.

“I’ve seen the crown. Everybody’s seen the crown. It’s so famous. It’s so iconic. When I was first thinking of doing this sale, I thought, ‘Wouldn’t it be great to track that crown down?’” Hatton said. “I’ve sold all sorts of wild things. But this is a little different.”

Shakur’s letters — many on lined stationary pages with neat hand-lettered script — were written in 1987 and 1988 to Kathy Loy, a fellow student at the Baltimore School for the Arts. The 42 pages chronicle their approximately two-month long romance, including a letter of regret for breaking up sent a year later. Loy provided the letters for auction.

“I’ll always be there for you,” Shakur wrote to her in one. In a poem, we writes: “Everything is so beautiful/since I fell in love.” The trove also reveal his friendship with fellow student Jada Pinkett Smith, who he mentions in one letter: “Jada told me she can see how much I love you.”

What interested Hatton most is the tone of the letters. Unlike Shakur’s tough public persona, the letters reveal a “sweet, poetic, sensitive young man.”