Do you know of any “gray area” ways to prove gambling losses in order to deduct them from my taxes? I recently hit a decent size jackpot, but like most players, I also lost my fair share over the past year. Unfortunately, I have no documentation of those losses. What I do have is records of my airfare, lodging and meals from the winning trip. Can I write those expenses off against my jackpot win? How about a fake diary of my gambling losses or using losing keno and sports tickets found on the casino floor and trash cans? Charlie G.

Sorry, Charlie, to both of your seditious solutions.

Expenses incidental to gambling, such as airfare, lodging, and meals are not deductible as losses. This family of write-offs are only deductible by professional gamblers (which you are probably not, as you would have kept meticulous records) or if you can show a direct business expense link, like a trade-show trip to Las Vegas.

As for if scouring trash bins or looking for littered losing tickets might be a possible solution to your winning woes, FORGET IT. The IRS expects some form of documentation that actually shows that losing gambling took place, and it better be Charlie G. who incurred those losses. The IRS has uncompromising, scrupulous means to determine if a gambler creates falsified documents. It is therefore not advisable to try to fake, find or forge losses.

The best way to avoid problems with the IRS in the future is to follow these simple rules:

ALL gambling winnings are technically taxable.

Factual, verifiable records are necessary to support winnings and losses pertaining to gambling.

Gambling losses are deductible only if deductions are itemized.

Gambling losses are only deductible up to the amount won in the same year. Losses cannot be carried forward to other tax years. If deductible, they must be deducted in the year of the loss or they are lost as deductions forever.

Gambling losses cannot be used to reduce other income. Gambling losses can only offset gambling wins.

You must report the full amount of your winnings on line 21 and claim your losses as an itemized deduction on Schedule A.

So, what size jackpot will trigger traceable paperwork? According to Uncle Sam, the payer must issue you a W2-G form if your Sbobet winnings are $600 or at least 300 times the amount wagered. This would be representative of winnings from dog racing, horse racing and state lotteries. Casino winnings are treated slightly different as a W2-G must be issued and filled out by the casino if a bingo or slot machine win is above $1,200, or the net proceeds from a keno win are greater than $1,500.

Oh yea, Charlie, another thing. Now that you have won a jackpot and received a W2-G, forget thinking you will somehow slip though the crack and Sammy wonÄ…t know of your tax liability. The IRS also receives a copy of the W2-G from the casino, and now their computers know of your good fortunes.

Because I am a few college diplomas shy of giving more technical tax advice, I highly recommend competent help for your tax obligation.

Gambling thought of the week: “The pro’s primary objective is to win money. Enjoying himself in the process is a welcome, but not altogether, essential requirement.” – Don Schlesinger