The Check Was Never Cashed

I'm not quite sure what the perfect phrase is.
"The check was never presented for payment."
"The check was never cashed."
"The check was never deposited."

THERE ARE CONSEQUENCES FOR YOUR (in-)ACTIONS!

I'm holding a grudge against a friend of mine. His life of chaos is slowly imploding on him and it's his pride or apathy or just plain stupid laziness that is the cause of much of his woe. He laments about money; customers don't pay enough, bills go up, car needs attention. So one day--out of the blue--I sent him a BillPay check for $100. It's one of those thoughtful gestures without s specific reason behind it. Well, that was in June and now it's September. The check has yet to clear.

The problem with BillPay with this credit union is that the money is taken out of my account when the check is written. I have no access to the funds. I have even asked him twice about it. The first time he just said oh yes, thank you. The second time he said that he can't find the check. It's in a pile somewhere.

What I wanted to really ask is, "Who the f**k holds onto a check for more than a day?" I either take it to the bank, run it through the ATM, or even mail it to the bank. This is completely unimaginable to me. I know he needs/could use the money. So why pretend? It just infuriates me when I offer assistance and it gets f**ked up by someone's laziness.

I've had this with him with other money issues. (I'm old fashioned and don't send cash in the mail). I tried sending him funds via ZELLE. It turns out he doesn't subscribe to ZELLE. I don't use any other method. I don't bank at his bank so I can't make a transfer, and I don't use PAYPAL. This will probably be the last time I do this which is--sadly--probably his goal. Sad