In the early 1340s, Lord Salisbury was married to Joan of Kent, a first cousin of the King, and a princess of England. Both Lord Salisbury and his bride were of exactly the same age, and both were in their early teens. Lord Salisbury entered into the marriage in good faith, without knowing that Joan had already, at the age of twelve, secretly married Thomas Holland, just before the latter left England on crusade. Upon returning to England in 1348, Holland declared that Joan was his wife and demanded that she be restored to him. An inquiry was instituted to examine the question, and it found that Joan had indeed been married to Holland, and that that marriage was valid in law; consequently, Lord Salisbury's own marriage to Joan was invalid. Lord Salisbury attempted to disrupt the proceedings by interfering with Joan's representatives and holding her captive so that she could not testify. Salisbury only released Joan after a second petition by Holland and the Church ordered Salisbury to do so. Joan testified she had consented to her marriage to Holland and it had been consummated. Following the findings of the inquiry, Lord Salisbury's marriage with Joan, Fair Maid of Kent, was annulled by the Pope in 1349. It is not known if Salisbury and Joan ever lived together during the years of their marriage for no records exist.
Military career
Lord Salisbury, by now twenty-one years of age, was showing signs of becoming a successful military commander. Despite the fiasco of his marriage with a member of the royal family, Lord Salisbury rose rapidly in the ranks of the army upon the strength of his own competence. He served as a commander of the English forces in France in many of the following years, including as commander of the rear guard of Edward the Black Prince's army in 1355, and again at the Battle of Poitiers in 1356, and further serving in 1357, 1359 and 1360. Later in 1360, he was one of the commissioners who negotiated the Treaty of Brétigny. The treaty led to a period of tranquility, during which time Lord Salisbury served on the king's council, working closely with King Edward III. In October 1361, the Edward the Black Prince married Lord Salisbury's former wife Joan. Lord Salisbury returned to the field in 1369, serving in John of Gaunt's expedition to northern France, and then in other raids and expeditions, and on some commissions that attempted to negotiate truces with the French. Lord Salisbury helped Richard II put down the rebellion of Wat Tyler. In 1385, he accompanied Richard II on his Scottish expedition. In 1392/3, Lord Salisbury sold the Lordship of the Isle of Man to William le Scrope of Bolton.