Mr. Mendelson is just playing; I think he knows better. Not only that, there's an eerie silence on Argentino or Mr. Mendelson verifying that Argentino was not employed anywhere when he was a professional video poker player. See, if Argentino was employed elsewhere, that eliminates the likelihood of his filing as an individual professional gambler. It leaves him with the option of starting up a Gambling Entity, but there are a number of consequences if that is what he did:
1) He has never mentioned starting a Gambling Entity.
2) Nothing the Gambling Entity did or accomplished can be attributed solely to Argentino.
3) There is no way to actually know, at this point, who was involved in the Gambling Entity.
I know as much about taxes as I do about The Flying Nun, but it has slowly, frighteningly dawned on me that that is more than most here.
Look, rub two neurons together and use your brains. Think about what a conversation would look like between somebody who lost five straight years playing video poker, offsetting big W2Gs with losses, who then decided after hitting a couple of big jackpots one calendar year that he was a professional gambler or that his Gambling Entity could reasonably be expected to show a profit. Gambling Entities are held to a different standard than most businesses. You have to demonstrate a likelihood of success, some model, some math, that makes long-term profits at least possible.
IRS Agent: So, I see you lost five years in a row to the tune of $450,000.
New Pro: Yes, but I'm now a professional.
IRS Agent: How's that? What's different?
New Pro: Well, I came up with a couple of new systems. I'm the only one who knows them. You wouldn't understand the math.
IRS Agent: Well, sir, that sounds reasonable to me. Let's give you a "professional" imprimatur.
Much of this origin story is just silly. If you're the face of a Gambling Entity, it's the same as heading a Pick Six conglomerate at the track or hosting folks who want to play slot machines on live feeds via other's contributions. There are myriad ways to maneuver money into one's own pocket via tax takeouts from the pools and then balancing wins and losses and all that. It's fifth grade scamming, but it probably still works today. Does anyone realize (except monet) how the suggestion of a 50/50 split with the Gambling Entity administrator deciding exactly when to stop a session -- does anyone realize how that opens the door to half a dozen different freerolls and tax scams?
Monet, speak up, man.
I'm busy with football, so use your neurons and ask, "If I were setting up tax trickeration and 50/50 freeroll scams, how would I do it?" The answers will come to you. Just pretend you're J.R.Ewing (yeah, I'm old).
If I get a chance later this month, I'll spell out how a Gambling Entity can provide cover for all sorts of nonsense, and how some tax manipulations can work. Regnis and monet both likely know this stuff better than me.




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