Prior to becoming the 21st President of the U.S., Chester A. Arthur served as the machine’s chief functionary – as Collector of the New York Customhouse, which brought in almost 80% of federal revenue and was the largest source of political patronage in the country.

Two presidents - Rutherford Hayes and James Garfield - tried to break the machine, with Garfield succeeding only temporarily. Hayes at one point nominated Theodore Roosevelt’s father to control the NY customhouse - a direct challenge to Conkling - but Conkling blocked him, helping form a young Teddy Roosevelt’s views on reform.

When Arthur became president after Garfield’s assassination in 1881, Conkling insisted that President Arthur continue to take orders from the NY machine. But Arthur pointedly refused and ultimately signed the Pendleton Civil Service Act, sharply limiting patronage in Federal employment.

In a twist of fate, in 1900, Platt, the surviving boss, famously pressed to have reform-minded governor Teddy Roosevelt nominated for Vice President to keep him from interfering in the machine’s business in Albany. While Platt managed to remove Roosevelt from Albany, he couldn’t foresee that TR would one day himself become President.