Plunkitt became wealthy by practicing what he called "honest graft" in politics. He was a cynically honest practitioner of what today is generally known as "machine politics," patronage-based and frank in its exercise of power for personal gain. In one of his speeches, quoted in Plunkitt of Tammany Hall, he describes the difference between dishonest and honest graft as working solely for one's own interests and working for the interests of one's party, state, and personal interest whenever they can.
He made most of his money through land purchases, which he knew would be needed for public projects. He would buy such parcels, then resell them at an inflated price. (This was "Honest Graft". "Dishonest Graft" according to Plunkitt, would be buying land and then using influence to have a project built on it.) Plunkitt was also a big party man, believing in appointments, patronage, spoils, and all of the corrupt practices that were curtailed by the civil service law. He saw such practices as both the rewards and cause of patriotism. He hated the civil service system that he believed would be the downfall of the entire United States governmental system.
The positive side of machine politics, as Plunkitt saw it, was the closeness between political bosses and their constituencies. He cites how Tammany bosses such as himself would assist the poor of New York in immediate and necessary ways (such as by providing emergency loans) while others, such as social reformers and the federal government, would only push for long-term improvements in the situation of the urban poor. Similarly, he argues that the machine listened to and defended the poor while others regarded them from a distanced, patronizing point of view. Thus, Plunkitt regarded the fragmented and independent format of machine governance to be the most perfect form of urban administration possible.
Plunkitt is also remembered for the line he used to defend his actions: "I seen my opportunities and I took 'em."