1. #1
    Fence
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    Important Question on Taxes, Reporting, and/or Cashing Out with Prepaid Debit Cards

    A friend of mine and I were having a recent discussion on whether it's risky if one would cash out winnings above a certain dollar amount via ATM machine (although we can't agree on the dollar amount?) with a prepaid debit card and not claim the winnings; again, not saying it is okay to scam any government and not pay your taxes. The dollar amount would surely be a major factor.

    For example, the Bookmaker card which is directly connected to an Australian bank (not the states) but still branded by ****. If you read the fine print from this bank, they maintain anonymity but would be forced to give records upon certain legal situations.

    I maintain it would be risky, he does not, thoughts?

    Also, are there any cappers here that don't keep records of their bets due to the blurred line of the laws with regard to online gambling and just deposit winnings over 10K in their banks and pay the taxes under "other income" instead of from “gambling winnings”?

    If so, how does this work? How do you explain 10K, 20K, 50K, 100K, (for example) when you get audited? Neither one of us are even remotely close to being high rollers like the above would indicate, but for the casual player, there has to be some kind of guideline for people to follow, right?

    Do you just explain that you have earned income offshore from consulting work? Not sure how one could go about doing this without a lack of documentation. But also, am not familiar with how the IRS would probe a situation like this? Seems like they would be happy as long as you reported any and all income albeit offshore derived or not.

    Where is a tax attorney when you need one? Ha-ha.

    Any help / input would greatly be appreciated - thanks!

  2. #2
    SharpAngles
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    How long have you worked for the IRS?
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  3. #3
    Fence
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    Funny! No, listen, there are many talented cappers on this site that must be able to provide some great insight on an issue that is gray. Professional curiosity.

  4. #4
    ans61201
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    Get losing bet slips in Vegas, offset wins with losses. Can even buy old ones (actually a thing for gamblers to offset their losses) I think guys will sell like 5,000 worth of losing tickets for 10 bucks lol

  5. #5
    hotcross
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    "don't ask, don't tell"

    "don't worry, be happy"
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  6. #6
    RudyRuetigger
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    You are basically asking others to help give you advice on committing a crime
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  7. #7
    Fence
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    Nope, no crimes. Please read carefully - I am looking for honest feedback on how some deal with a non-black-and-white issue in the most ethical way.

    Don't be afraid of the boogeyman, he is not going to jump out and arrest you because you decide to discuss a complicated tax and gambling issue on a sportsbook forum.

    Nevertheless, I've scoured forums and the web and it seems that many are not on the same page and the information out there seems to lack substance. Perhaps it is because there are so few people that actually win a significant amount of money, or so I've heard.

    I certainly have no problems consulting with an attorney for the best advice and posting back what I can find out. But my intention is to find people on here who do this the right way... ...the ethical way. So, I thought I'd check to see what some of the smart people on here do.

    Appreciate all of the feedback and welcome any additional insight on what seems to be a taboo and tight-lipped subject.

  8. #8
    BuckyOne
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    Quote Originally Posted by ans61201 View Post
    Get losing bet slips in Vegas, offset wins with losses. Can even buy old ones (actually a thing for gamblers to offset their losses) I think guys will sell like 5,000 worth of losing tickets for 10 bucks lol
    There are some flaws in that tactic. Can that person prove they were there in that state? Let's say the tickets add up to 10k in one day and he never took a dime out of his bank accounts and bought gas with his debit card in his hometown?

    If the guy won the money in Vegas - it flies a little better.

    The debit cards are made for small transactions - buy groceries, etc. Doing 300 cash withdrawals at an atm in a years time does not sound like a good idea.
    Last edited by BuckyOne; 02-14-18 at 09:49 AM.

  9. #9
    vividjohn45
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    I'm in Oklahoma. Under state law it's feloniously illegal to place online wagers of any kind. . The attorneys have never busted just a regular Joe citizen on it but in 2011 they busted a cop on it. (Could become compromised to owed mafia) (Online horsebetting) he pled guilty to the felony and got a 5 yr deferred sentence. Which means fulfill terms of ur probation and charges are dropped. So the regular Joe citizen here has to make up their own mind. If online wagering. Save receipts of tickets because you have to declare tax winnings on federal 1040 tax form on other income line. (Same with Oklahoma.s tax form) this avoids the tax evasion felony leaving one only exposed to a possible Oklahoma deferred felony for placing a online wager. All said check the state law in gambling where you live. Under federal law there are no criminal charges for regular Joe citizen placing wagers but a federal and possible state felony charge for tax evasion.
    Last edited by vividjohn45; 02-14-18 at 10:27 AM.

  10. #10
    Fence
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    Thanks Buck and John; good information. Why am I not surprised state and federal laws aren't congruent on said issue. There's no way people who online gamble would ever be held accountable in large numbers, just doesn't make sense - there's too many people that do it - IE: just look at the superbowl and the amount of money that is wagered online annually. Just doesn't seem like a proactive pursuit unless you have a target on your back from some other vice.

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