One California city has been quietly collecting $5,000-per-incident fines from short-term vacation rental owners. And if the regime is struck down, the city may owe half a million dollars back.

Former constitutional law attorney David Koslow joins Tim Kowal and Jeff Lewis to break down two Appellate Division challenges that expose a structural flaw in how cities administer and collect STVR fines, and why SEC v. Jarkesy may be the tool that finally pries these cases open.

Key points:

• The $1,000 cap hiding in plain sight: Government Code §36901 sets a default $1,000 ceiling on city fines—but Cathedral City and several other Coachella Valley municipalities have been imposing $5,000 first-offense STVR penalties for years.
• Forfeiture swallowed the first case whole: In Montanaro v. City of Cathedral City, the pro per defendant said the fine was "draconian"—but never said "excessive fines clause." The Court of Appeal dismissed on forfeiture. “Draconian,” says the court, is not the same as “excessive.” 🧐
• Jarkesy goes local—maybe: SEC v. Jarkesy (2024) held that the Seventh Amendment requires a jury-trial forum when the government chooses between administrative and court proceedings for civil penalties. Cathedral City can prosecute STVR violations as misdemeanors in court or through an administrative citation—which, says Koslow, is exactly the kind of forum election Jarkesy targets.
• The vendor-as-judge problem: Data Ticket, Inc.—a private company that collects the city's fines—also supplies the hearing officers who adjudicate them. The structural conflict is not subtle, and it has already spawned its own litigation.
• Pro per litigants are walking into a trap: STVR fines are deliberately calibrated below the cost of hiring an attorney, yet high enough to hurt. The result is a steady stream of self-represented defendants making fatal procedural errors that appellate counsel cannot fix.
• The Coastal Commission wrinkle: Coastal cities face a distinct constraint—the Commission treats STVR bans as restrictions on public coastal access, effectively foreclosing outright prohibitions in the coastal zone.

If you advise cities on enforcement program design, represent property owners facing administrative fines, or litigate issues of constitutional preservation and forfeiture, this episode is required listening before your next city council meeting or appellate brief.