Robertson was known to have allied with the GOP Half-Breed faction,[2][3] which as a whole supported moderate civil service reform[4] and emphasized the issues of protectionist tariffs as well as industry.

During the 1880 presidential election, a three-way battle initially emerged between the Blaine faction, Half-Breeds, and conservative pro-spoils system Stalwarts led by Conkling.

[6] Ultimately, an alliance between the Blaine faction and Half-Breeds successfully nominated dark house candidate James A. Garfield, who promised to appease the Stalwart agenda during the campaign to ensure party unity.

[2] Once elected president, Garfield betrayed his vows, an example being his appointment of Robertson to New York Collector of the Port and customhouse head without consulting Sen. Conkling[3][7] in a rebuke of the latter's political machine.

"[7] The Stalwart leader voiced opposition towards Garfield's appointment of Robertson by arguing that presidents were expected to obtain the agreement of senators from the states they sought to give positions to, though Richardson asserted:[7] What was really at stake, was whether or not Conkling would control New York.Conkling and his New York senatorial colleague Thomas C. Platt resigned from their seats in protest, expecting to be immediately elected to their same positions by the state legislature that would serve as a rebuke to President Garfield.