Richard: What says Lord Stanley? Will he bring his power?

Messenger: My lord, he doth deny to come.

- Shakespeare, Richard III, V.iii

Thomas Stanley, First Earl of Derby

Thomas Stanley (1435?-1504) was a major figure in England's War of the Roses, betraying three kings and crowning a fourth.

Stanley began his political career in 1454 as a squire to Lancastrian king Henry VI. But having married the sister of Yorkist lord Richard Neville, Earl of Warwick, Stanley secretly held Yorkist sympathies, and at the Battle of Blore Heath in 1459, declined to enter the fray on his King's behalf, despite having a large force close at hand.

When the Yorkists finally came to power under Edward VI, Stanley was rewarded with the office of Chief Justice of Cheshire. But when Warwick switched sides and supported a brief Lancastrian restoration in 1471, Stanley once again followed his brother-in-law and switched sides to support the Lancastrian claim. Then, after Warwick's fall, he came back over to the Yorkists, and was rewarded with the office of Steward of the Royal Household.

In 1482 Stanley married his second wife Margaret Beaufort, mother of exiled Lancastrian claimant Henry Tudor. But despite this marital alliance with the Lancastrian faction, Stanley remained in favor with the Yorkist court, advancing up the ranks under Edward and then Richard III by becoming a privy councilor and then Constable of England.

Stanley declined to choose sides in the 1483 rebellion on Henry Tudor's behalf, despite his wife's deep involvement with the Lancastrian cause, but when his step-son faced Richard at the Battle of Bosworth Field in 1485, Stanley declined to take the field on Richard's behalf, and Henry won the day. Stanley's refusal to fight was decisive, and to him fell the honor of placing Richard's crown on the new king's head, as Henry Tudor became King Henry VII. Stanley's real reward was even greater power, as Henry confirmed all his offices and created him first Earl of Derby.

In the final analysis, Stanley emerges as a shrewd student of the shifting winds of political fortune, always switching sides at exactly the right moment. Surviving the downfall of several kings from both of the competing houses, Stanley managed to hold office continuously from 1461 until his death in 1504. Kings triumphed and kings fell, but Stanley always came out a winner.