Explosive Tupac letter to Madonna heading for auction

Tupac Shakur broke off his relationship with Madonna because she was white.

That's the shocking revelation of an apologetic letter the hip-hop star wrote to the singer from prison. A letter that comes to Gotta Have Rock and Roll's July 28-ending auction with a hugely conservative $100,000 estimate.

Tupac Shakur Madonna letter

Shakur's letter urges his ex-girlfriend to be careful

The three page handwritten letter, which Shakur wrote in January 1995 while serving time for sexual assault, reads, in part:

"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.

"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. I never meant to hurt you."

The pair had an 18-month relationship after meeting in 1993.

Yet this letter suggests Shakur believed his relationship with a white woman was proving detrimental to his image. It's not known if Madonna ever received the letter.

Shakur's letter ends on a portentous note.

"Please be careful," he urges. "There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm! Let my 5 bullets be proof of that!"

Shakur would be killed in a drive-by shooting a year later.

Shakur's personal items have huge appeal with collectors, such is his influence on hip-hop.

An essay Shakur wrote from prison auctioned for $172,275 last year – a record for hip-hop memorabilia. We're anticipating this letter to beat that record – such is its fascinating content and famous recipient.

A sexually explicit letter Shakur wrote to an unknown woman achieved $34,300 in January, while a ticket to the boxing match he attended the night he was murdered in Las Vegas sold for $24,500 at the same auction.

Please sign up to our free newsletter to receive exciting news about music memorabilia auctions.

Featured products

Elvis Presley Authentic Strand of Hair
Elvis Presley Authentic Strand of Hair
Sale price£399
In stock
Fidel Castro signed certificateFidel Castro Signed Certificate
Fidel Castro signed certificate
Sale price£2,995
In stock
King Henry VIII Autographed DocumentKing Henry VIII Autographed Document
King Henry VIII Autographed Document
Sale price£55,000
In stock