Tupac Shakur (Lesane Crooks) also spent time in Clinton Correctional, a stint that later became the subject of a court case. After several of Madonna’s items went on sale in an online auction, Madonna filed a lawsuit asserting that the items were hers and could not be sold. One of these items was a letter from Shakur, who Madonna dated in the ‘90s. He’d written it to Madonna while imprisoned at Clinton Correctional. Parts of the letter were later published by TMZ . In it, Shakur breaks up with Madonna gently, telling her that while he cannot hurt her image as her boyfriend, she would hurt his.