
19. Subjected to Pressure from His Wife and From His King, the Earl of Derby Played Both Sides
As King Richard III marched out to meet Henry Tudor, Thomas Stanley, 1st Earl of Derby, was conflicted. His family had originally been Lancastrians, the side championed by Tudor. However, Stanley had switched sides and defected to the Yorkists, now headed by Richard III. Stanley was handsomely rewarded for betraying the Lancastrians with lands and estates, and powerful government positions. As a result, he was greatly indebted to the Yorkists. However, he 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 at home, Stanley dealt with the pressure by playing both sides. He secretly contacted his stepson, to sound out the possibility and potential rewards of defecting back to the Lancastrians. Things got awkward, however, when King Richard got wind of that correspondence. He seized Stanley’s son as a hostage to ensure against his father’s treachery. He then ordered the Earl to join the Yorkist army with his contingent, which Stanley reluctantly did.



