You can't be taxed for gamba winnings that you immediately lost. You never really made that income. The grandma in Reno who won $500 at nickel slots and lost it all

over the rest of the weekend ain't paying taxes on that $500, no one is coming after her over it. Same thing for Bossman going up to 30 banderooskis and losing it all

over the next ten minutes
All the juice Austin got could be classified as gifts, which the receiver doesn't have to pay taxes on. The giver should file a gift tax return if the gift(s) are valued at more than $17,000. I'm sure some of Bossman's juicers are above that level. But NOBODY GIVES A SHIT NOBODY FUCKIN CARES
Where it gets interesting is if Bossman used gamba winning money to buy CS skins, buy shoes, buy computer equipment, buy crispy crackarooski, buy anything. He could say no I used juice for that, but there's records of him withdrawing gamba winnings. That's income and is taxable. But again NOBODY GIVES A SHIT NOBODY FUCKIN CARES
BUT, EVENTUALLY, the Virginia Department of Taxation and the IRS will get around to giving a shit, if Bossman didn't file returns, didn't declare the income, didn't pay the taxes, because fuckin RATS keep ratting on him