Can't Let Go or Lessons Learned?

My friend The Alcoholic asked me to lend him my car today.

In the past, I have lent it to him, but that was before I bought a new car last year. One time when he borrowed it, he returned it to me with graffiti on the window (someone had drawn on it with a sharpie), which I had to clean off by myself. Another time, he admitted that he had been driving around in it drunk, even picking me up in it when he came to return it to me and driving me in it whilst drunk. I didn't know till a week later that he had been drunk, because he didn't tell me till then.

So, we've had our issues. And now he's in Alcoholics Anonymous, and becoming a changed person. Good for him. But do I want to lend him my new car so he can go to the doctor's office to pick up medication? No, I don't. I could've said, "Why don't you take a cab?" or "Why don't you take the bus?" But instead, I just flat out said, No sorry, but I can give you a ride if you want.

He came back at me with, "Don't you trust me?" and thus ensued a heated text war of sorts. It wasn't as bad as it would've been back before his sobriety, but the fact that it was over text rather than in person or over the phone still irked me. This is a conversation you want to have with me via text? Okay, fine.

I brought up the issues of the graffiti and him driving drunk and said I just felt weary of lending him something when he's proved in the past to be disrespectful of me and my property. He told me that I needed to let things go. But to me, it's more of a "lessons learned." I've been burnt twice (probably more) by him, so why would I enter that arena again?

Also, I wouldn't ask a friend to borrow his or her car. I just find that a lot to ask of someone. Maybe I'm just a prude when it comes to loaning things? Even though I lend out books and DVDs and CDs all the time?