Prediction markets have been taking up a significant amount of oxygen in the U.S. gaming space. My current favourite reads on the topic are 50¢ Dollars, by Adhi Rajaprabhakaran, an early (former) Kalshi employee and pro prediction market trader, and The Event Horizon by gaming industry veteran Dustin Gouker.
Changes to the way gambling winnings are taxed in the United States have been in the news recently. In summary, as of January 1, 2026, U.S. taxpayers can write off up to 90% (down from 100%) of their documented gambling losses against their winnings, meaning that some people could owe tax even if they “break even” in a calendar year. Efforts in Congress to undo the 90% cap (with catchy names like the FAIR BET Act and the FULL HOUSE Act) have yet to gain real traction. Additional changes, like a tweak to slot-reporting which aims to raise the W-2G threshold to $2,000 and index it to inflation, won’t kick in until the IRS updates its regulations, so casinos will continue issuing W-2Gs at $1,200 for now.
If you are reading this (and aren’t related to me), it’s probably because you're interested in the Canadian gaming landscape and maybe even Canadian gaming law. If that’s the case, then you’re likely familiar with the Bodog case in Manitoba. A few weeks ago, Justice Harris released his reasoning in the Bodog case, granting the applicant, Manitoba Liquor and Lotteries, everything it asked for. If you’re an operator in the Canadian market (excluding Ontario) or supplying goods and services to operators in this market, this decision may impact you. How? You’ll have to read below (or generate an AI summary of this article) to find out.
If you’re paying attention to the Canadian gaming scene, you’re aware that the Manitoba Court of King’s Bench granted an injunction prohibiting Bodog (operated by Il Nido Inc.) from offering or advertising online gambling services to Manitoba residents.
In Ontario's regulated iGaming market, the Alcohol and Gaming Commission of Ontario (AGCO) has been clear that operators are accountable for the conduct of their affiliates. When those affiliates cross a regulatory line, the operator is responsible for the financial penalties.
The online payments space is chaotic. Companies evolve and expand quickly. Processing chain roles get blurred. The branding is slick, and the legal language rarely keeps up with the pace of financial engineering.
Welcome to the Wild West
