Henry Holland, Third Duke of Exeter was yet another descendent of John of Gaunt. His grandmother Elizabeth was John’s daughter. He had a claim to the throne after the death of Henry VI, something which Edward IV may have been all too aware of being the aforementioned earl’s brother-in-law.

Henry had been Richard of York’s ward.  Richard married his eldest daughter off to Holland in order to secure the dynastic links and power base.  Unfortunately for both Holland and the Duke of York it would appear that the Exeter lands weren’t terribly productive.  Consequentially Holland was always in finical difficulties which didn’t help his disposition overly.

He developed an unsavoury reputation early in his career when he seized Lord Cromwell’s estate at Ampthill and had him falsely accused of treason.  He also extended his land holding through the convenient method of fraud. This was all dragged through the law courts and resulted in no one wanting to be sheriff of Bedfordshire on account of Holland’s bullying tactics. In the end he aligned himself to one of Cromwell’s enemies in order to further his cause – thus demonstrating beautifully the fact that the Wars of the Roses could be said to be a bunch of local disputes that got seriously out of hand.

There wasn’t any great love between the Yorks and Holland so it probably didn’t unduly bother Holland that his alliance with Lord Egremont was one of the causal factors in him being in the Lancastrian army chasing Richard of York around the countryside in December 1460.  Henry Holland was a commander at the Battle of Wakefield on December 30 1460.  Presumably he hadn’t enjoyed being imprisoned in Wallingford Castle in 1455 after Richard assumed the title of Protector when Henry VI was incapacitated on his father-in-law’s orders.  In reality, Richard’s descent from two sons of Edward III gave him a better claim to be protector than Holland who thought he ought to have the job. He was descended from John of Gaunt and the First Duke of Exeter had been Richard II’s half-brother.  York’s claim came from the fact that he was descended from the second surviving son, Lionel of Antwerp via the Mortimer line.  The Mortimers had been Richard II’s heirs.  As if that wasn’t bad enough Holland wasn’t given a role of any importance. Holland threw his toys out of his pram, fermented rebellion in the north and consorted with the Scots – he was lucky that a year in Wallingford was all that he got.

He was, at least, consistent in his support for the Lancastrian cause being present not only at Wakefield but also at the Second Battle of St Albans and Towton.  He scarpered from the latter and managed to escape to France where he joined Margaret of Anjou.

Unsurprisingly family relations were at an all time low by this point. Not only was his attainted of treason but his wife Anne who had been married off to him when she was eight-years-old sought a legal separation from a man who’d gained a reputation for being deeply unpleasant one way or another. They had one child, Anne Holland who would be married off to one of Elizabeth Woodville’s sons from her first marriage, and pre-decease her unfortunate father.

In 1471 he returned to England with the Earl of Warwick who had stopped being Yorkist and become a Lancastrian in what can only be described as a giant strop when Edward IV stopped listening to his advice.  Warwick died at Barnet. Henry Holland though badly wounded managed to reach sanctuary in London. Edward had him rounded up and sent to the Tower.  He had for a time been the Constable of the Tower so at least he was familiar with his accommodation.

By the following year Anne was able to have the marriage annulled, she went on to marry Thomas St Leger but Edward IV seems to have welcomed Henry back into the fold as he was part of the military expedition that set off to make war on the French. It wasn’t a roaring success from the wider population’s point of view as they’d been heavily taxed and expected a decent battle at the very least. What they got was a treaty whilst Edward IV received money to go away and an annual pension.

As for Henry Holland?  He had an unfortunate accident on the way home.  Apparently he fell overboard.  The Milanese Ambassador suggested that the accident was caused by a couple of burly nautical  types picking him up and throwing him…

Oxford Dictionary of National Biography