He was awarded the BA degree of the Royal University of Ireland in 1893, and took his MA in 1894.
Rutledge continued his studies in London, and was called to the bar by the Inner Temple in 1897.
He devilled in the chambers of Mr Justice Horridge for 1897–8, after which he joined the Northern Circuit and practiced at Liverpool from 1898 to 1908.
Following the resignation of Sir Sidney Maddock Robinson, Rutledge succeeded as Chief Justice of the High Court of Judicature at Rangoon on 4 December 1924.
Rutledge was a strong supporter of the government of Sir Harcourt Butler and its policies.