Keep records of ticket purchases, payment slips, and unredeemed tickets. The theory here is to have a separately filing taxpayer, an entity, properly formed for the sole purpose of gambling. Whether one's gambling activities constitute a "business" or not is to be determined on a case-by-case basis by the Taxation Office and is subject to appeal to various Tribunals and Courts. In the first two cases, the gamblers won substantial amounts of money and the Taxation Office was trying to levy tax on those winnings, arguing that the gamblers were in the "business" of gambling. Make sure there are no shoe prints on the losing tickets, once you drop a pari-mutuel ticket and someone steps on it, it is generally "void" for tax deduction purposes. The lesson learned in this matter Jimmie Clemons v Commissioner is if you are looking to take a position of Professional Gambler Status then retain a tax pro.
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