paying taxes gambling

lets say i won $150,000 on a big parlay.

Do not pay.Take a chance.Keep a portion for the taxman if he catches up with you 2 or 3 years down the road. In Canada we pay zero taxes on winnings even if it is 20 million.

Does your sportsbook report and file WG-2 forms with IRS?

Taxes 

Let's say you actually worry about it if/when it ever happens......

If you're reporting gambling gains then you should be able to offset them with your lifetime of losses.

It is easy to tell you not to report winnings, but you might want to take a look at 26 U.S.C. 7201 ( tax evasion and jail time ) and 26 U.S.C. 7206 ( tax evasion and jail time ). And as to your statement that all you'd have to do if caught is pay a penalty, do you know what the penalty is ? You have to pay the amount of the underpayment, plus a 75% penalty over and above the underpayment, plus interest on both from the time of the underpayment. You can find that at 26 U.S.C 6663. If you want to play audit roulette, make sure you are informed of possible consequences.

And just for kicks, those advising you not to pay might want to take a look at 18 U.S.C.371, which provides fines and up to 5 years jail time for anyone who, IN ANY MANNER, conspires with another to defraud the USA out of money the USA has a right to.

Best of luck to all who choose to gamble.

If you withdrew the money slowly enough and in small enough amounts, you will probably be OK, but it is always possible for the IRS to stumble across what you are doing.

The IRS has about 100,000 employees. Do you think a few might be sports fans and gamblers ? Do you think a handful may even have "stumbled" upon Covers and other sites for sports information and "expert" opinions ? Just asking.

checks under 10,000 dont raise red flags from everything I've been told by people who actually know what they're talking about. Always smart to stash some away just in case but seriously who pays taxes on gambling unless you are forced to by the casino after taking them big which is a good problem to have.

Money orders like western union and moneygram under 750 never even consider paying taxes on. If worried i'd slowly take the money out in increments like this.

Like lbcake said the losses in the past should also offset them. Not hard to goto a casino or a track and pick up a bunch of losing tickets to give proof to offset as well. Did the IRS ever give you a tax refund on your gambling losses?

My post above was meant to inform the OP, not to advise a course of action. The information was offered in the same spirit as those who try to help others on this site with helpful sports information so they can make informed decisions.

In that same spirit, I can tell you that monitoring checks over $10,000 is not the only way the IRS obtains the information leading to prosecutions or civil fraud charges in large gambling winnings cases. Sure, someone wins a few bucks at the track or a casino, it is unlikely to interest the IRS or attract its attention. However, the bigger the score, the more they care. And, it might surprise you to know that one of the most common ways people get caught is not your $10,000 check scenario. It is because the big winner talks about it and talks about not paying the IRS. Then, people with a grudge ( ex-wife ? ) , or other issues ( disgruntled co-worker ? ) find out about it and decide to rat you out. Making matters worse, if they pursue it, they find out they can get 30% of whatever the IRS collects from you under IRC 7623, the IRS Whistleblower statute. Of course, if you never say a word about your winnings to anyone, you are less likely to be ensnared this way.

Now, again, I am not suggesting this is likely; nor am I suggesting a course of action. But it does happen and I think more information is usually better than less. And, once again, in that same spirit, you should know that the IRS prosecuted one of those "grab a bunch of losing tickets" cases that you mentioned in a high profile prosecution against a Boston accountant and attorney back in the 1980's. They are also aware that you don't even need to visit a casino; losing tickets are for sale for this purpose on Craigslist. But hey, this particular crime ( IRC 7207 ) only carries a year in the slammer and you've been running lucky so why not roll the dice one more time.

woah relax 1129 ken. dont shoot the messenger. people got in trouble for downloading pirated movies and music also. same kind of thing here few people get made an example of from time to time.

Messier---I could not be more relaxed, in part because I simply convey truthful, accurate information without advising a course of conduct that suggests breaking the law simply because you probably won't get caught. It is also information that is all the more helpful because even educated people like yourself apparently are not aware of it.

My message indicated only that there are consequences if you do get caught and the larger the underpayment the higher the likelihood that a Covers member might get into serious trouble. Frankly, if you want to talk about "shooting the messenger", I am the messenger whose message you decided to gratuitously dismiss and "shoot" because  you thought you had better information  from "people who actually know what they are talking about." You don't.