25. Stuck Between a Rock and a Hard Place
King Richard III gathered his forces to face the threat of Henry Tudor, and marched out to meet his challenger. The King’s forces included a big contingent commanded by key Yorkist loyalist and supporter Thomas Stanley, 1st Earl of Derby. The earl was conflicted, however: his family had been Lancastrians, but he had defected to the Yorkists. He was handsomely rewarded for that switch with lands and estates that made him and his already rich family even richer. He was also appointed to powerful positions in the royal government, and was thus indebted to the Yorkists.
However, Stanley also happened to be married to Henry Tudor’s mother, so he was the challenger’s stepfather. Stuck between the rock of loyalty and the hard place of peace and tranquility in his own house, Stanley decided to play both sides. So he secretly contacted his stepson to explore defection. King Richard however found out, and seized Stanley’s son as a hostage for the Earl’s good behavior and insurance against treachery. He then ordered Stanley to join the Yorkist army with his contingent, which the earl reluctantly did.