He was the son of Thomas Holland, 2nd Earl of Kent and Alice Fitzalan, daughter of Richard Fitzalan, 10th Earl of Arundel. He was also nephew of Richard II of England. On his father's death in 1397 Holland became 3rd Earl of Kent, and was elected a Knight of the Garter. At that time Kent's uncle Richard II was removing from power Thomas of Woodstock, Duke of Gloucester, and his associates, and sent Kent to arrest his own uncle - Richard Fitzalan, 11th Earl of Arundel. In reward he received a share of the forfeited estates, and on September 29 was created Duke of Surrey. Yet another uncle John Holland was created Duke of Exeter on that day as well.
Holland, along with many of Richard's advisors, was arrested after Richard's deposition by Henry IV. In the end he had to forfeit the honors and estates he had gained after the arrests of Gloucester and Arundel, and thus went back to just being Earl of Kent.
Early in 1400 Holland, along with his uncle John (now Earl of Huntingdon instead of Duke of Exeter) plotted to kill Henry IV and free Richard II from prison and return him to the throne. The plot failed and Holland was captured and executed.
He left no children by his wife, Joan, daughter of Hugh, Earl of Stafford. He was succeeded as earl by his brother Edmund.
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|width="30%" align="center"|Preceded by:
New Creation
|width="40%" align="center"|Duke of Surrey
|width="30%" align="center"|Followed by:
Extinct
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|width="30%" align="center"|Preceded by:
Thomas Holland
|width="40%" align="center"|Earl of Kent
|width="30%" align="center"|Followed by:
Edmund Holland
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