Henry FitzRoy, 1st Duke of Richmond and Somerset duchy, the title of Duke of Richmond was important as the earldom of Richmond had been held by his grandfather King Henry VII and by his great-grandfather Edmund Tudor, 1st Earl of Richmond. The earldom of Nottingham had been held by Richmond’s great uncle Prince Richard of Shrewsbury, Duke of York, the second son of Edward IV. Seeing Henry’s obvious pride and affection for his sturdy little son, many of those who witnessed Richmond’s elevation must have wondered if this was what the King had in mind. To support his new status, Henry granted his young son an annuity of
Henry Stafford, 1st Earl of Wiltshire who married Robert Radcliffe, 1st Earl of Sussex, and Anne, who married firstly, Sir Walter Herbert (d. 16 September 1507), an illegitimate son of William Herbert, 1st Earl of Pembroke, and secondly, George Hastings, 1st Earl of Huntingdon. After the execution of the 2nd Duke of Buckingham, his widow, Katherine Woodville, married Jasper Tudor, second son of Owen Tudor and King Henry V's widow, Catherine of Valois. After Jasper Tudor's death on 21 December 1495, Katherine Woodville married Sir Richard Wingfield (d. 22 July 1525). Katherine Woodville died 18 May 1497. After her death, Sir Richard Wingfield married Bridget Wiltshire,