A million-dollar poker run sounds like the ultimate loophole, until the CRA decides it looks like a job. We talk with criminal defence lawyer Michael Mulligan about a Supreme Court of Canada leave decision that leaves standing a key ruling on poker winnings and Canadian income tax, and the real lesson it carries for anyone who treats gambling like a serious side hustle or a full-time living.

We get into why most gambling winnings in Canada are generally tax-free under the Income Tax Act, then zero in on the exception: when the activity becomes business income. Hours spent, strategy, risk management, consistent profits, and relying on poker as your main source of income can all push you over the line. And if it’s business income, it can cut both ways, because deductions for losses and expenses may be available just like any other business.

Then we shift to a topic that frustrates the public and the courts alike: criminal cases that take too long. We unpack Jordan’s hard timelines under Charter section 11(b), what counts as delay, and how the Supreme Court now treats “exceptionally complex” prosecutions with many accused and mountains of disclosure.

If you care about Canadian law, taxes, and how court decisions affect everyday choices, hit subscribe, share this with a friend, and leave us a review. What do you think should count as “work” when luck is involved?

Follow this link for a transcript of the show and links to the cases discussed.