Theodore was born on the 22nd of December 1888, in Annapolis, Maryland, where he entered the US Naval Academy after graduating from St Paul’s School in New Hampshire. He graduated the Academy first in his class in 1909 and received a commission to Ensign on the 5th of June 1911. Two years later, he was assigned to the USS Florida for sea duty and it was his actions while leading a company during the landing party at Veracruz that would later earn him the Medal of Honor. The citation reads:

For distinguished conduct in battle, engagements of Vera Cruz, 21-22 April 1914. Ens. Wilkinson was in both days' fighting at the head of his company and was eminent and conspicuous in his conduct, leading his men with skill and courage.

Theodore received the Medal of Honor on the 4th of December 1915, and later deployed to European waters on board the USS Tennessee to assist with the evacuation of Americans in Europe unable to leave because of the outbreak of World War 1. During and after the war, Theodore served as the head of the Experimental Section of the Bureau of Ordnance, followed by serving as a gunnery officer on board the USS Kansas.

By 1945, he had commanded five vessels, headed four government bureaus, and commanded the Battleship Division 2, the South Pacific Amphibian Forces, and the III Amphibious Force, reaching the rank of Rear Admiral. Theodore testified before a joint congressional committee during the investigation over the bombing of Pearl Harbor. He stated that he thought the Japanese would have avoided a direct confrontation with the US and assumed they would attack somewhere in the South Pacific. Theodore would go on to help develop the strategy known as leapfrogging that became one of three main factors that helped defeat the Japanese. This strategy simply allowed the allied forces to occupy positions behind the Japanese positions to cut off their supply lines. With leapfrogging as a tool, Theodore would receive three Distinguished Service Medals by January of 1945 and he was ordered to the Navy Department for his final assignment as a member of the Joint Strategic Survey Committee of the Joint Chiefs of Staff. On the 21st of February 1946, Theodore Stark Wilkinson Jr died in a ferry accident at the age of 57. He was able to save his wife Catherine but was unable to save himself. The couple had one child and Theodore is buried in Arlington National Cemetery: Section 2, Lot 3645.