If Madonna Loved Tupac, Why Didn’t She Bail Him From Prison?

LEGENDS & ICONS OF HIP HOP - Wanda Davidson Post

Delray Richardson answers the question on if Madonna loved Tupac, then why didn’t she bail him out of prison?


Tupac dated Madonna between 1993 and 1995 and revealed in a letter to the singer that he ended their relationship because she was white.The break-up letter from the late rap star, dated January 1995, reveals he ended their relationship because he feared dating a white woman could jeopardize his career.

In June 2019, the New York State Appeals Court ruled Madonna couldn’t sue her former friend Darlene Lutz for selling the letter to an online auction house after she filed for an emergency court order to stop the sale of letters, photos, a hairbrush, and even a pair of panties that she had once worn.

Delray Richardson is a producer that was close to Tupac Shakur and in the video above, he is asked by a Tupac fan why Madonna never bailed out Tupac if she loved him. The answer was quite simple by the producer. The rap star was married to Keisha Morris at the time, and believes Madonna did not want to bail him out since he would just be with his then wife.


Tupac also had letters from Will Smith’s wife, Jada Pinkett-Smith, during his prison stint. Shakur began the letter by apologizing to Madonna, writing:

‘I haven’t been the kind of friend I know I’m capable of being’.

‘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,’ he wrote later in the letter.

‘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.’

Shakur also brought up an interview Madonna had given, in which she said she would ‘rehabilitate all the rappers and baseball players’.

‘Those words cut me deep seeing how I had never known you to be with any rappers beside myself,’ Shakur wrote.

‘It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things.’