
3. Waiting Until the Last Minute Worked Out Great For Stanley
Stuck between the rock of loyalty to Richard III, and the hard place of peace in his own home, Thomas Stanley decided to play both sides. While professing loyalty to Richard, he secretly contacted Richard’s challenger, Henry Tudor, to explore defection. Richard found out about the double-dealing, however, and seized Stanley’s son as a hostage for the Earls good behavior and insurance against treachery. He then ordered him to join the Yorkist army with his contingent, which Stanley reluctantly did. The challengers met at the Battle of Bosworth on August 22nd, 1485, but Stanley remained undecided, and kept his men out of the fight, while waiting to see which side looked like a winner. A livid Richard III sent Stanley a message, threatening to execute his son unless he immediately attacked the Lancastrians, only for the Earl to coolly reply: “Sire, I have other sons“.
Richard ordered Stanley’s son executed, but the order was not immediately carried out, and soon, it was too late. At last, Stanley made up his mind that King Richard was losing the battle, and ordered an attack – against Richard and the Yorkist forces. That tipped the scales against Richard III, who launched a final desperate attack seeking to reach and cut down his challenger, only to get cut down himself. After Richard’s death, Stanley found his fallen crown in some shrubs, and personally placed it on the head of Henry Tudor, who became Henry VII, founder of the Tudor dynasty. Stanley’s stepson and new king of England generously rewarded the treacherous earl for procrastinating until the last minute.



