He was the third son of Thomas Holland, 1st Earl of Kent and Joan "the fair maid of Kent, daughter of Edmund of Woodstock, a son of Edward I. His mother later married Edward, the Black Prince. Holland was thus half-brother to Richard II, to whom he remained loyal the rest of his life.
Early in Richard's reign, Holland was made a Knight of the Garter (1381). He was also part of the escort that accompanied the queen-to-be, Anne of Bohemia, on her trip to England.
Holland had a violent temper, which got him in trouble several times. The most famous incident occured during Richard II's 1385 expedition to Scotland. Ralph Stafford, eldest son of the Earl of Stafford, killed one of Holland's esquires. Stafford went to find Holland to apologize, but Holland killed him as soon as he identified himself. The king had Holland's lands seized. Their mother died during this time, it is said of grief at these events.
Early the next year Holland reconciled with the Staffords, and had his property restored. Later in 1386 he married Elizabeth, daughter of John of Gaunt. He and Elizabeth then went on Gaunt's expedition to Spain, where Holland was constable of the English army. After his return to England he was created Earl of Huntingdon, on June 2, 1387. In 1389 he was appointed chamberlain of England for life, admiral of the fleet in the western seas, and constable of Tintagel Castle. During this time he also received large grants of land from the king.
Over the next several years he held a number of additional offices: constable of Conway Castle (1394), governor of Carlisle (1395), and then governor and then constable-general of the west marches towards Scotland. His military servies were interrupted by a pilgrimage to the Holy Land in 1394 (which may be connected with his earlier troubles with the Staffords).
Holland helped the king take down Thomas of Woodstock and Richard Fitzalan, 11th Earl of Arundel in 1397. He was rewarded by being created Duke of Exeter on September 29.
He then went with Richard on the king's 1399 Ireland expedition. When they returned the king sent him to try to negotiate with Holland's brother-in-law Henry Bolingbroke. After Henry deposed Richard and took the throne (as Henry IV), he called to account those who had been involved in the downfall of Thomas of Woodstock, and in the end took away all rewards Richard had give them after Thomas' arrest. Thus Holland became again merely Earl of Huntingdon.
Early the next year Holland entered into a conspiracy with his nephew Thomas Holland, Earl of Kent, Thomas le Despenser, and others. Their aim was to assassinate king Henry and return Richard (who was in prison) to the throne. Their plot failed, Holland fled, but was caught and executed. Among those who witnessed the execution was Thomas Fitzalan, 12th Earl of Arundel, son of the Earl of Arundel who Holland had arrested some years before.
Holland's lands and titles were forfeited, but eventually they were restored for his second son John Holland, 2nd Duke of Exeter.
From Froissart's Chronicle: Sir John Holland kills Lord Ralph StaffordReferences