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Apart from routine official duties, Holbein now occupied himself with private commissions, turning again to portraits of Steelyard merchants.
He also painted some of his finest miniatures, including those of Henry Brandon and Charles Brandon, sons of Henry VIII's friend Charles Brandon, 1st Duke of Suffolk, and his fourth wife, Catherine Willoughby.
Holbein managed to secure commissions among those courtiers who now jockeyed for power, in particular from Anthony Denny, one of the two chief gentlemen of the bedchamber.
He became close enough to Denny to borrow money from him.
He painted Denny's portrait in 1541 and two years later designed a clock-salt for him.
Denny was part of a circle that gained influence in 1542 after the failure of Henry's marriage to Catherine Howard.
The king's marriage in July 1543 to the reformist Catherine Parr, whose brother Holbein had painted in 1541, established Denny's party in power.

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