Madison said that if he thought it would be acceptable to the people when asked to ratify the Constitution, he would favor a freehold requirement [for the right to vote]. "The freeholders of the Country," he held, "would be the safest depositories of Republican liberty." Elaborating on this insight in a characteristically gloomy way, Madison went on: "In future times a great majority of the people will not only be without landed, but without any sort of, property. These will either combine under the influence of their common situation; in which case the rights of property & the public liberty, will not be secure in their hands: or which is more probable, they will become the tools of opulence & ambition, in which case there will be equal danger on another side." -- Kevin Gutzman, James Madison and the Making of America, p. 116
NOTE: when I dictated this passage, Siri wrote: "Elaborating on this insight in a Characteristically Gloomy Way..."
I guess she thought that "Characteristically Gloomy Way" was a street address. It is probably right next to "Morose Circle" and "Suicidal Depression Boulevard."