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So either y'all do a 5754 and each pay your income tax separately (way too much bother), or you just make a guess as to how much income tax Tyler will owe on this. If you live in Nevada, and make a middle-class income, it's gonna be 25%.

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Unless of course Tyler will itemizing his deductions and declaring losses that equal his gambling winnings in which case the net tax on his gambling winnings would be 0.

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I kinda alluded to that earlier when I said if he itemizes to run TurboTax with and without the W2G and split 25:75 whatever the difference is, but you can't do that until the year is done. I also figure if Tyler needs staking from Pick he probably is not the itemizing type.

If he IS the itemizing type, then he gets to worry about having too much income and having his schedule A deductions start phasing out. Even if you itemize, if you make too much you can't deduct all of your losses... at some income level the Feds start whacking off deductions. So if you have a couple million dollar income, and $100K in winnings and $500K in losses, you're still gonna pay tax on a fair fraction of that $100K despite actually being a big loser for the year.

Congress sucks.