Why don't more businesspeople run for mayor of America's biggest city? Host Jamie Rubin and political commentator Ross Barkan discuss who's not on the ballot in the 2025 mayoral race and why. They analyze Mike Bloomberg's formula for political and managerial success while dissecting former Gov. Andrew Cuomo's comeback attempt. In a thought experiment, they game out exactly how a wealthy outsider might spend $100 million to capture City Hall in a wide-open race. And Barkan delivers a brutal assessment: The current mayor, he estimates, has a 5% chance of survival in what may be the most consequential election in decades.