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For centuries, the nation’s political leaders have loved their games of chance. Andrew Jackson owned fighting cocks and raced horses. Richard Nixon helped finance his first congressional race with his World War II poker winnings. Teddy Roosevelt noted that the professional gamblers he knew “usually made good soldiers.” But even among this crowd, McCain and Obama are distinctive. For both men, games of chance have been not just a hobby but also a fundamental feature in their development as people and politicians. For Obama, weekly poker games with lobbyists and fellow state senators helped cement his position as a rising star in Illinois politics. For McCain, jaunts to the craps table helped burnish his image as a political hot dog who relished the thrill of a good fight, even if the risk of failure was high.
From the looks of it, Obama plays poker with buddies, for a few dollars at most, while McCain hits the casino’s hard. Fine with me - it’s his money, and if he wants to gamble it away, who cares - although a legitimate question would be what he would do with public money. But there’s an more serious problem here. Reporting losses and winnings to the IRS. Here are some relevant instructions for filing from IRS Form W-2G. Although that form is for declaring winnings, note the form also has clear instructions even if you are gambling and losing money as well:
Generally, report all gambling winnings on the “Other income” line of Form 1040. You can deduct gambling losses as an itemized deduction, but you cannot deduct more than your winnings. Keep an accurate record of your winnings and losses, and be able to prove those amounts with receipts, tickets, statements, or similar items that you have saved.
It is pretty obvious why Uncle Sam wants to know if you are winning significant sums of money gambling. Why would Uncle Sam care if you were losing? Well, for starters, gambling is an all-cash transaction. If you don’t regulate it, you are just inviting people to launder money through casinos.
If McCain is winning and not declaring — that’s a crime. If he is losing and not taking the deductions, that is peculiar for a lot of obvious reasons. It means he never wins. If he is losing his own money and not taking the deduction, it looks like he is trying to hide a problem. If he is losing other people’s money that certainly raises questions about influence peddling if they have business in front of his committee. Whether he is winning or losing, it doesn’t take a whole lot of imagination to see how a lobbyist bankrolling the senator’s marathon craps session might be using this as a way of funnelling money into the senator’s coffers without drawing attention to the transactions.