Kiwi Pot Pie
Hellovan Onion
There is another possibility. Josh Moon is a control freak. He may be spending all that money on his favorite cow BossmanJack to keep him loaded with money so BMJ can keep gambling and doing drugs. Like was mentioned, Josh does it for content despite his own rule about interacting with lolcows. Josh is a deranged and evil man and loves having the ability to control someone's entire life.I consider those payments to Shuffle.com to be solid evidence to support the statement that "Joshua Connor Moon is a gambling addict."
He has done this before. Remember Chris-chan and how Josh controlled Chris's finances and who he could contact (though to be fair, Chris was fucked either way since Josh was competing with several other psychos to control Chris's life). And like with Chris, Josh might really think he is doing BMJ a favor by giving him money.