AITA for refusing to lend a book back to someone who couldn’t return my favorite video game and destroyed another item I lent him?

I have a friend, let’s call him Jack, who I’ve known for ~10 years. We met through a sports team we’re both on and have been close friends ever since. <br><br>We frequently lend things to each other. We live about 5 minutes away from each other, so we find it to be very convenient. <br><br>He has borrowed:<br><br>&#x200B;<br><br>1. My PS4 controller. He promised to return it that weekend, but when he did, it was broken. It was the first PS4 controller ever made, so I imagine it was finicky. I didn’t really care all that much about it, so I just said it was no problem and moved on. <br><br>&#x200B;<br><br>2. My copy of The Last of Us. This is where things started to go downhill. He said he wouldn’t be able to return it for awhile because he had a lot going on and didn’t have time to play it. It took him two months to return it, and when he did, he gave it back without the plastic wrapping on the game case. I didn’t want to be a jerk, so again, I brushed it off and took the game back. <br><br>&#x200B;<br><br>3. My car. He wanted to borrow my car for a week to move into a new house. I was a little hesitant because my car is my most prized possession, but he insisted that he would be careful with it. I trusted him and handed over the keys. <u>He failed to return it on time and ignored all my calls/texts</u>. He eventually ended up returning the car with scratches in the front wheel wells, scratches on the front bumper, and a large scratch on the side of the car. He claimed he didn’t do it and that he was just in an accident. I didn’t want to be paranoid, so I just took his word for it, but I was livid at the state my car was in. Because we’re friends, I forgave him and moved on. <br><br>&#x200B;<br><br>Fast forward a few months, he asks me if I could lend him a copy of my favorite book, Shogun. I told him up front that no, I couldn’t lend it to him because he has a bad history of borrowing and returning things. I was afraid he wouldn’t return it or would destroy it. He said he understood and respected that, but he wanted me to know that he does return things (LOL) and that I shouldn’t automatically assume he was going to break my book. He said he would even give me his car as collateral in case he didn’t return the book. I still said no because I didn’t want to have to take his car and I didn’t want him to feel pressured into keeping his word. He tried to change my mind multiple times, but I wouldn’t budge. <br><br>&#x200B;<br><br>He eventually called me an asshole and told me to fuck off after I wouldn’t budge. He told our friends I was an asshole and I’ve gotten some heat from my friends about it. <br><br>AITA for not lending him my book, or was he being stupid by thinking I’d trust him with anything after all the shit he pulled?