However, Ms. Lutz added, “She didn’t take the route that Beyoncé did” — a reference to the pop star’s exhaustive personal archiving system.

Madonna’s representatives did not immediately respond to a request for comment. The singer had previously said she did not know Ms. Lutz was in possession of the items until last year when the gossip site TMZ published the letter from Shakur.

Dated Jan. 15, 1995, the letter was written during Shakur’s incarceration at New York’s Clinton Correctional Facility for sexual assault, the year before his shooting death at age 25 in September 1996. In the letter, he alludes to his reasons for ending a relationship with Madonna.

“For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting,” Shakur wrote. “But for me at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.”

A second letter in the lot was an unsent draft written by Madonna to another former boyfriend, the actor John Enos. In it Madonna described two of her rivals, Whitney Houston and Sharon Stone, as “horribly mediocre,” adding, “They’re always being held up as paragons of virtue and some sort of measuring stick to humiliate me.”

Ms. Lutz said she came into possession of the items while frequently hanging around during that time in Madonna’s orbit, where she “tended to be a repository for a lot of stuff where people just thought: ‘Get rid of it.’” That included large piles fan mail that were often not examined at all, Ms. Lutz said. “I knew all of the assistants and stuff would get thrown in boxes and they would just go, ‘Hey, here’s some more.’”