Thomas, Earl of Desmond, succeeded his father James, often called the Great Earl, on James’ death in 1462. The civil wars in England were then in progress: the Wars of the Roses. Recently, one of the great Desmond opponents, Butler, Earl of Ormond, was executed after the battle of Towton where he had taken the losing Lancastrian side. The earls of Desmond backed the triumphant Yorkists under the recently crowned King Edward. Earl Thomas defeated a Butler invasion force, brought to Ireland by the brother of Ormond, at the battle of Piltown in 1462. Earl Thomas was appointed king’s deputy in March 1463.
In what appears a gross historical anomaly – given his house’s support for King Edward – Thomas, Earl of Desmond, was beheaded in Drogheda in February 1468. He had been replaced by Sir John Tiptoft, Earl of Worcester, as king’s lieutenant. Some historians have written about an old claim in the Tiptoft family to Youghal and Inchiquin, which the Desmonds controlled. Many others recycle the tale of how King Edward’s wife was upset by something once said by Earl Thomas. The story goes that when Edward checked with Thomas about this, Thomas is said to have advised Edward to reconsider his marriage to Elizabeth, the daughter of Woodville, a low-ranking private gentleman. The King confided this to the Queen, who began to think of schemes to destroy Thomas. She is said to have had a warrant drawn up for Thomas’s execution and to have forged the King’s signature on it.
The story of the Queen’s involvement in Thomas’s execution is said to lack any basis in contemporary reports. Instead, the historian Art Cosgrove presents a picture of King Edward as an active promoter of the rule of law, and of Tiptoft, known in England as “the Butcher”, as his willing instrument in the Dublin government. Cosgrove lends credence to the theory that Earl Thomas was the subject of repeated reports for his imposition of coign and livery on the Old English of the Pale. (The Desmonds had imposed this set of Gaelic chiefs levies for generations in Munster.)
The disaffection of the Desmond from the English dates from the execution of Thomas at Drogheda. For the coming twenty years or so, in the reign of Thomas’s successor, James, this is manifest in a retreat from government into fratricidal strife among the Desmonds themselves. When Edward died the throne transferred to his brother, Richard III, and so intense was the strife in Munster that in 1484 Richard sent the bishop of Annaghdown to molify James for the loss of his father at Drogheda. Otway Ruthven tells us that the Bishop offered James many inducements to rturn his family to their allegiance.
King Richard is shortly killed at Bosworth by the Lancastrian Tudor, Henry VII, and it is in the reign of Henry that the Desmonds first seek a European ally in order to put a Yorkist pretender on the throne. The support to bring this scheme to fruition came from Burgundy. In 1469 King Edward’s sister, Margaret, married Charles, the new Duke of Burgundy. The pretender was Lambert Simnel who came toIrelandin 1487. Later, in December of that year, James was murdered at Rathkeale. We do not know if the English were involved.