Originally Posted by
baccarat_king
Challenging the IRS in a situation like this probably requires accountants and lawyers (whose cost) would probably exceed the expectation. It's not like there is a huge good samaritan contingent out there that is feeling horrible about gamblers who tip heavy, and then want to offset the tips against wins (as losses)
Representing yourself in tax-court, against the IRS could be very dangerous.
There are many things that are unfair, especially with regard to the IRS. You just deal with it the best you can. Believe me, this (deducting tips), is probably one of the least substantive complaints against the IRS. In any case, people shouldn't be tipping that much anyway. (and those that do tip on extreme levels are hardly worried about the tax implications).
I'm always worried about the tax implications. It annoys me no end when I finish a trip and they have net out by 2-3K.
Personally it feels wrong, I look at trips like this like a profit center and if the IRS does too (by wanting to tax the win) then they should realize a profit center comes with costs.
Furthermore it annoys me even more when the Hosts come back with 'oh you won, we didn't comp you for the entire trip, but you still made out' after you kick the dealers the profit they think you won and you walk out with less money than you started with.