Winston Churchill said, “no one pretends that democracy is perfect or all-wise. Indeed, it has been said that democracy is the worst form of government except for all those other forms that have been tried from time to time.” City of Miami residents would be wise to heed Churchill’s advice since their mayor is proposing changing the city’s government by eliminating the professional manager and appointing a staff controlled by the mayor. Voters may reason that ceding policy and management authority to a single elected individual is a better form of democracy than what they enjoy today. But are residents really better served when power is consolidated under only one politician? We get some answers by examining the Progressive Era of the early 1900s, which was rife with corruption flowing from executive mayor governments. The mayor made policy and executive decisions in what was known as the “boss system.” If the “grease” was not an outright bribe, it was some sort of “influence peddling” resulting in decisions benefiting special interests, not the community. The subsequent revolt against those “political machines” led to the rise of Council Manager governments akin to the corporate structure. In Miami’s current government, residents are stockholders, who pay taxes and own the city.