This article Thomas of Woodstock and Shakespeare’s Twisted History | Ancient Origins (ancient-origins.net) begins as follows:-
“….William Shakespeare wrote ten history plays. Of these, one of the most famous is Richard II . The play Richard II , written around 1595, is based on the rule of King Richard II (reign 1377-1399), but one of the main characters in the play is Thomas of Woodstock, Duke of Gloucester, despite the fact he is dead for its entirety….”
I should imagine that the unfortunate Richard II often wished the awful man had never been born. Richard was plagued by powerful uncles, and the youngest, Thomas of Woodstock, the first Duke of Gloucester, was a nasty piece of work. He was an unpleasant, supposedly pious bully who clearly suffered from the ‘youngest son syndrome’, if there is such a thing. And today’s Prince Harry thinks he’s always been a mere second best? He should try having the Black Prince, Lionel of Clarence, John of Gaunt and Edmund of Langley ahead of him in the pecking order. Harry has had it easy in comparison. As the article says, Thomas “had a rather sizable chip on his shoulder”.
But not all Dukes of Gloucester were admirable, and Thomas was certainly determined to be as powerful as he possibly could. In Richard’s best interests, of course. Oh, of course. Thomas was also very pious. Hmm. I can never accept that someone is truly pious when they commit awful crimes. It’s all a front. In my opinion.
He was born 7 January 1354/5 at Woodstock, and was the sixth surviving son of Edward III (who could certainly churn out spare after spare after spare….) Thomas grew up to be a relatively effective military man, and eventually married Eleanor de Bohun, an exceedingly wealthy heiress….except that she, most annoyingly, had a sister, Mary, who was the co-heiress. Thomas, dear fellow, did all he could to force Mary to take the veil (perhaps that’s where George of Clarence got the inspiration to try the same with Anne Neville?) But Thomas’s own brother, John of Gaunt, outwitted him, had Mary abducted and married to his, Gaunt’s, son and heir, Henry of Bolingbroke. (Boooo!) She died before Bolingbroke usurped Richard II and then murdered him at Pontefract.
However, I digress. Thomas didn’t take this financial setback very well, and needless to say his relationship with Gaunt deteriorated somewhat. In fact, Thomas’s relationships with a number of people deteriorated, including his ill-fated nephew, Richard II. I don’t think Thomas liked anything about Richard. Certainly he set out to nit-pick and complain, conspire and thwart at every turn. Ultimately he headed a powerful group of magnates, the Lords Appellant, who opposed the advisors and friends around the king. The Battle of Radcot was won by the Appellants, who set about teaching Richard a lesson and executing his friends and advisors. As you do.
When, eventually, Richard regained the upper hand, he in turn set about punishing the Appellants. Heads rolled. Thomas was arrested and imprisoned at Calais where surprise surprise, he died (it’s believed on 8 September 1397). To put it plainly, he was murdered. Strangled probably. As far as Richard was concerned, this particular uncle was no great loss. If I were Richard, that’s certainly how I’d feel.
Anyway, you can read much more in the above article, and at a lot of sites on the web. The demise of Thomas of Woodstock is, after all, a very well-known case. But, strangely, it’s Richard who usually gets the blame. I’ve come to the conclusion that it’s something to do with kings called Richard, because the third monarch of that name hasn’t fared well in the blame game either. But Thomas of Woodstock deserved what he got, and I for one have no sympathy for him, He was a right royal rat.
I suppose I ought to apologise for being flippant with my illustrations, because the subject is serious enough, but I fear I cannot. In case you hadn’t noticed, I just dislike Thomas of Woodstock!
murreyandblue 
Thomas of Woodstock’s birthdate was 1355, not 1344/45. He was actually closer in age to his two nephews, Richard II and Henry IV, than to his older brothers, so he missed out on any of the “glory” of the earlier part of the Hundred Years War. John of Gaunt’s whisking little Mary Bohun away to become Henry’s bride while Woodstock was out of the country must have been galling to Woodstock who saw his income cut in half. This suggests Gaunt did not have much use for his youngest brother.
But Gaunt also stiffed Edmund of Langley, the brother closest to him in age. Although some authors say that Langley (created Duke of York by Richard II in 1385) supported Henry IV because of his affection for his dead father, while alive Gaunt refused to help pay for York’s heavy expenses incurred in helping Gaunt strive (unsuccessfully) for the crown of Castile, causing his younger brother to suffer financial difficulties the rest of his life. This doesn’t speak well for Gaunt’s family affections.
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Sorry about the date typo, which I’ve corrected. Thank you for pointing it out.
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I have often tried to understand the admiration some writers have for Woodstock. He seems to be singularly unpleasant, even by the low standards of the day. I can only think it was that he was an advocate of killing foreigners. As I have said before, the fundamental issue of this reign (and Henry VI’s) was that most of the political class wanted war, but no one was willing to face the fact that war is a costly business, especially when you are dealing in a war of attrition with an enemy with a larger population and far larger financial resources. Personally, I would have told Woodstock he could have all the war he liked, if he could persuade Parliament to finance it.
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I have to add that the more I see of Woodstock and Gaunt, the more I admire Langley. Had to run a dukedom on a shoestring, but did not spend his entire life moaning and being bitter. Gaunt treated him like dirt, but not even that embittered him. He hadn’t the proverbial pot, but he wasn’t constantly complaining about the King giving stuff to others. He was a man, not a whining baby.
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