Well, there was the prostitution. I wouldn’t call it “unsavory” however: I’ve always had a pretty relaxed view towards sex, so while I’m not proud of it, I’m not ashamed of it by any means. I discuss it pretty openly with friends.
I also let a homeless prostitute move in with me. This gave her a place to live and “work” out of, and I charged her per day, payable in cash or drugs. She was also “supposed” to contribute cash towards rent on top of. Of course, she never did, despite the fact that all together, what I was asking her to pay was 1/2 what she was paying to live in the hotel she was at when I met her. I ended up getting evicted, of course. It was my fault: I’m generous and “understanding” to a fault, and I never pushed her hard enough to actually pay me. I always felt too guilty asking her to leave. She knew a sucker when she saw one and completely took advantage of me.
There was the “boosting” – we would go from store to store shoplifting baby formula, then take it to a bodega and sell it for $10 a can. Ended up with a shoplifting charge, but not before I made thousands of dollars that way. We mostly hit up Walmarts, which I genuinely don’t feel bad about, because Walmart is fucking evil IMHO.
My credit was already pretty destroyed before the drugs, but I did a lot of things that didn’t help matters whatsoever. For example, I had a PayPal debit card that was linked to my bank account. At some point I realized that if I created a “dummy” PayPal account, I could send money from my main account to my dummy account, then from the dummy account right back to my main account. The cash would then appear on my PayPal debit card, regardless of whether I had the money in my bank account or not. I could then go retrieve the money from an ATM. This basically allowed me to overdraft my bank account to the tunes of hundreds of dollars, which wouldn’t have been possible with my bank’s debit card. I thought that was pretty clever.
The worst thing I ever did was steal a gold bracelet from my mother. I had played in her jewelry box since I was a kid so I thought I knew the history of every item. One day when I was incredibly sick I went into the jewelry box and selected the bracelet, which I didn’t recognize. I assumed it was some random thing her ex bought for her and that she wouldn’t be attached to it, but it ended up being something her mother had given to her shortly before her death a year or so earlier. Oops. To make things worse, my mom then gave her jewelry box to a “friend” in order to hide it from me. The “friend” pawned every single item in it, something which I absolutely never would have done. She’s forgiven me, but I still feel incredibly guilty about it.
Those are the ones that immediately come to mind, though I’m sure if I thought it about it harder I could come up with some pretty wacky things that I’ve done to come up with money.