In this episode of "The Trial Lawyer's Handbook" podcast series, litigation attorney Dan Small unpacks the prosecution of Ted Anzalone, a top aide to Boston Mayor Kevin White, through two alleged money laundering schemes: a "birthday gift" check-planting operation that sowed jury confusion and led to acquittal, and a clearer $100,000 cash structuring scheme using sub‑$10,000 cashier's checks to evade bank reporting. Despite a compelling trial win on the structuring count, the U.S. Court of Appeals for the First Circuit reversed, holding that "the law is the law" and Congress hadn't yet criminalized that type of financial activity. Mr. Small reflects on the limits of prosecutorial creativity, a memorable bench rebuke and how the case ultimately spurred lawmakers to close the loophole – too late for Anzalone, whose conviction was vacated, but paving the way for successful prosecutions thereafter.