Henry demonstrated his gratitude to his “right dearly beloved father” by creating him Earl of Derby on 27 October 1485, and the following year confirmed him in office as High Constable of England and High Steward of the Duchy of Lancaster, besides granting him other estates and offices. In 1486 Stanley also stood as godfather to Henry’s eldest son, Arthur, Prince of Wales. Even so, at the time of the Lambert Simnel rising of 1487, there may have been some concern that the Stanleys were again hedging their bets, and “there was relief in the royal host when the Stanleyites came in at Nottingham”. The aftermath of the Battle of Stoke, which crushed this rising, brought still further rewards for Stanley – notably the lands forfeited by Viscount Lovell, Sir Thomas Pilkington, and Sir Thomas Broughton in Lancashire and elsewhere. In 1489 the Stanleys again made a notable contribution to the army raised by Henry to suppress a rising in Yorkshire. Less successfully, Stanley’s brother William unwisely supported the later pretender Perkin Warbeck, and was, at last, executed for treason in 1495.
Throughout his career, alongside the main performance of national events, the preservation and enhancement of Stanley’s own role as regional magnate was a very important sideshow. Change of regimenever really weakened his grip on the key offices of Chester and Lancaster and throughout his life Stanley consolidated the legacy he had inherited from his father and extended his hegemony and that of his family across the north-west. Given the range of his office-holding both regionally and at court, he did not need to draw ruinously on his own resources to dispense patronage on a grand scale and he was active in the arbitration of local disputes; even state matters were regularly referred for his personal adjudication. That said, ‘good lordship’ also had its harder face and the Stanleys brooked no opposition and tolerated few rivals in their areas of dominance.
Stanley was made Constable of England by Richard III towards the end of 1483, the year in which Edward V and Richard, Duke of York (the Princes in the Tower) disappeared from their confinement in the Tower of London. As Constable (originally a position which constituted command of the royal armies), Stanley was formally responsible for anyone who entered or left the Tower – then the most secure of royal palaces. In this capacity, and as a loyal member of the Ricardian regime at the time, he can be considered at the very least an accessory to the Princes’ deaths, since once they had entered the security of the Tower they were never seen or heard of again. That said, since the Duke of Buckingham preceded Stanley as Constable of the Tower, Stanley could realistically only have had such an opportunity after Buckingham’s rebellion and execution in October and November 1483 on becoming Constable. This would have given Richard and Buckingham – considered a far more likely contender for killer of the Princes – ample opportunity to dispose of the Princes between their confinement in May 1483 and the rebellion in October. Also, since Buckingham’s uprising was expressly staged in favour of Henry Tudor’s claim to the throne – rather than that of the missing Edward V – it seems reasonable to assume that Buckingham knew the Princes were already dead prior to his rebellion and, hence, Stanley succeeding as Constable. However, it has also been suggested that in view of his being the stepfather of Henry Tudor and deserting Richard at Bosworth, it is not inconceivable that Stanley was at least in part responsible for the Princes' death after Henry's accession. The Princes, still living, would have presented just as much of a problem to Henry's occupation of the throne as they did to Richard's.
