Yesterday TMZ published a letter Tupac Shakur wrote from prison to Madonna in 1995. It’ll be sold at an online auction starting July 19th, with a starting bid of $100K.

In the letter, Tupac explains why he broke up with Madonna and apologizes for being a bad friend. We know your very first question is HOW DOES THIS RATE AS AN APOLOGY? 

Answer: It’s pretty good!

  1. He starts with the apology. Which is as it should be…but often isn’t.
  2. We don’t know what’s been blurred out, but he’s explaining what she did that triggered the breakup. Ordinarily, we argue that “here’s what you did” has no place in an apology. An apology is not about cataloguing what the other person did wrong; it’s about owning what YOU did wrong, and trying to make it right. In this particular case, though, pointing out that a fellow celebrity exhibited racist behavior (and I think we can agree that though Madonna was joking in saying something like “I’m off to rehabilitate all the rappers and basketball players” when asked about dating Tupac, it’s a pretty hurtful thing to say as well as a sweeping generalization about black men) is more excusable. Tupac is trying to educate her, and since she’s a prominent person with a lot of influence, she isn’t the only one who benefits from education. He may have prevented her from issuing bigoted generalizations in the guise of jokes in the future.
  3. I think the “can u understand that?” and “can u feel me?” questions are materially different from “will you forgive me?” — which regular readers know I am vehemently opposed to asking during an apology. Asking for forgiveness puts the other person on the spot and puts the onus on them rather than keeping it on the apologizer. The apologizer needs to own the act of mending the relationship, not the apologizee. But I think Tupac’s questions are conversational, to make sure Madonna’s following, to humanize, to try to sound direct and immediate even though he’s writing from far away. To me, these phrases add a heartfelt quality, an attempt to be clear and to be understood.
  4. Is calling himself “a young man with limited experience with a extremely famous sex symbol” a bit of an excuse? Sure. Is it understandable as a reason why he failed to communicate with her clearly in the past? Also sure.
  5. There is something very sweet about his plea to her to be careful and wary.
  6. Asking her to visit is not, I think, putting her on the spot, because this is a letter and not a face-to-face conversation or phone call. (This is in part why letters are an excellent medium for apologies.) His last line (“It’s funny but this experience has taught me not to take time 4 granted,” followed by a little heart) is touching, and in light of his death the next year, haunting.

I would be remiss in not noting that an apology Tupac made earlier in the year, to the victim of the sexual assault he was convicted of perpetrating that put him in prison in the first place, was not so good.

As the victim addressed the court, Mr. Shakur stared intensely at her. Then he got up and apologized to her. But he went on to say: “I’m not apologizing for a crime.” He added, “I hope in time you’ll come forth and tell the truth.”

It was not clear what he was apologizing for. Later he apologized again, saying, “I got so involved in my career that I didn’t see this coming, that I wasn’t more focused.” He also apologized to “the youth of America,” but he did not elaborate.

“I have no shame,” he said. “I don’t feel shame.”

This takes no ownership at all. As we’ve said repeatedly, if you don’t think you did anything wrong, don’t apologize.

The last letter of Tupac’s sold at auction for $170K. It too was written in prison, and it talks about the reflection and spiritual growth he’d been working on. It too reveals some serious soul-searching. In it, he talks about leaving Thug Life behind and developing an identity as a strong black male.

Who knows who would have become if he’d lived?

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