Bailey joined the Royal Navy as a cadet in the training ship HMS Britannia in September 1896. As a midshipman in HMS Centurion, he took part in the Seymour Expedition for the relief of Peking legations in 1900 during the Boxer Rebellion, for which he was mentioned in dispatches. He was promoted to acting sub-lieutenant on 27 August 1901 and subsequently confirmed in that rank from the same date. In November 1902 he was posted to the protected cruiser HMS Doris, but was first lent for a couple of weeks to HMS Hogue for sea-trials. He was promoted to lieutenant on 27 February 1903. He qualified as a gunnery lieutenant from 1905 to 1907, and served in the battleship HMS Africa from 1908–10 and in the cruiser HMS Leviathan from 1911-12. Following two periods on the staff of the Whale Island gunnery school at Whale Island, he was promoted to commander in June 1914. Bailey served as gunnery officer HMS Erin during the first years of World War I. In 1916 he was appointed to the staff of Vice-Admiral David Beatty and served as a fleet gunnery officer on HMS Lion, having been recommended by Flag-Captain Ernle Chatfield as "one of the best gunnery officers in the Navy". In November 1916 he was appointed Flag Commander to Admiral Sir David Beatty when the latter was appointed to the command of the Grand Fleet first in HMS Iron Duke and then the new fleet flagship HMS Queen Elizabeth. Bailey was promoted to Captain in December 1918, received the D.S.O. He worked as deputy director of the Operations Division of the Naval Staff. Bailey appointed naval attaché in Washington, D.C. in March 1921. In January 1923, he took command of the 9th Destroyer Flotilla of the Atlantic Fleet. In 1925 he was appointed Naval Assistant to the First Sea Lord who was then Lord Beatty. He then returned to sea when he was given command of HMS Renown. Bailey was promoted to Rear-Admiral in 1931 and April 1931 to October 1932 served as Chief of Staff to Admiral Sir Ernle Chatfield, who was at that time Commander-in-Chief Mediterranean Fleet. In February 1933 he became Assistant Chief of the Naval Staff, and in August 1934 Bailey succeeded Rear-Admiral William James in command of the Battle Cruiser Squadron, flying his flag aboard HMS Hood. During training exercises off the Spanish coast on 23 January 1935, the Hood and collided. Bailey and the captains of both ships were court-martialed for the incident. It was the first court-martial of an admiral since the First World War. Following acrimonious proceedings, Bailey and the captain of the Hood were both acquitted, while the court found the captain of the Renown guilty. However, the Admiralty subsequently reviewed of the verdicts and declined "to absolve Rear-Admiral Bailey from all blame". In 1936, the Hood needed to be refitted and recommissioned. The Admiralty had planned for Bailey to transfer his flag to the Renown. However, there were continued bad feelings about the collision and courts-martial among the officers of the Renown, and Bailey pleaded successfully to be allowed to remain with the Hood until she returned to Portsmouth. Bailey was appointed President of the Royal Naval College, Greenwich in 1937. In 1938 he was appointed as a Knight Commander of the Empire. Bailey was promoted to Admiral on retirement in 1939. Bailey was recalled to active service after the outbreak of the Second World War. In June 1940, the Admiralty created a secret committee, named the Bailey Committee for its chair, which examined the level of naval assistance to be sought from the United States. The American admiral Robert L. Ghormley was given a copy of the report in August 1940, and Bailey, the committee and Ghormley met regularly through the autumn, and developed important processes for the exchange of information about intelligence, technical and operational matters. In 1922, Bailey married Mildred Bromwell; they had a daughter and a son. Bailey died on 27 March 1942 after a short illness.
