The boom in legal sports betting and CFTC-regulated event contracts has blurred a once-clear line: when is a bet just a bet, and when is it a financial product? This panel takes on both worlds—the OBBBA's new 90-percent cap on gambling loss deductions under Section 165(d) and the bipartisan repeal effort now targeting its treatment of break-even and losing years, alongside the unsettled character, timing, and reporting questions raised by prediction markets and event contracts that look economically like wagers but may be taxed like something else entirely. Overlaying the federal picture is an escalating federal-state conflict: the CFTC asserts exclusive jurisdiction over event contracts as swaps, while a growing number of states insist they are gambling—suing the platforms, invoking their gaming laws, and enacting the first prediction-market transaction taxes—so that a single contract can be a federally regulated derivative and state-law wagering at the same time. Panelists will work through the session method, professional-versus-casual status, and information reporting, and consider the growing strain on a system that can tax arguably identical economic bets in radically different ways depending not just on how they are characterized, but on which sovereign is doing the taxing.