Derby was betrothed in 1498 to Elizabeth Wells, the daughter of John Welles, 1st Viscount Welles, by Cecily of York, the daughter of King Edward IV and Elizabeth Woodville. A papal dispensation was obtained for the marriage. However Cecily died that year. By indenture dated 17 December 1505 Derby married Anne Hastings, the daughter of Edward Hastings, 2nd Baron Hastings, and Mary Hungerford, and by her had two sons and a daughter:
The failure of Thomas Stanley's grandfather, Lord Stanley, to come to the aid of King Richard III at Bosworth contributed to King Richard's defeat. Lord Stanley, who was by then married to the future Henry VII's mother, Margaret Beaufort, is given a major role in Shakespeare's Richard III. Lord Stanley's son, George, Thomas Stanley's father, was held hostage by King Richard, as noted in this speech given to Lord Stanley in Act IV, scene V of the play:
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