As a captain, Gilligan was not tactically sophisticated but was adept at inspiring his players. His Sussex teams were not consistent but became attractive to watch; under Gilligan's direction the team ranked among the best fielding sides in England. The off side fielders were nicknamed the "ring of iron". His "Wisden" obituary stated: "In two or three seasons by his insistence on fielding and on attacking cricket and by his own superb example he raised Sussex from being nothing in particular to one of the biggest draws in England." According to "The Times", Gilligan's captaincy laid the foundations for the county's relative success in the 1930s. In the official history of Sussex, writer Christopher Lee suggests: "The ten years from 1920 to the end of Gilligan's captaincy in 1930 saw the blooding of some of the most famous names in Sussex and England cricket. Gilligan himself was a mixture of amateur brilliance and professional thoroughness which inevitably brought about criticism."