Court fools seem often to have been recruited in a haphazard talent-spotting manner; this is not the only example of someone noticing a suitable candidate on their travels and making the necessary introductions for them to be brought to court.
Note that the letter describing this young fool as a suitable replacement for an elderly Sexten is addressed to Thomas Cromwell at the peak of his power. It suggests that the appointment of a fool for the king wasn’t a trivial matter.
The image is not a portrait of the fool mentioned; it was chosen simply as it appears to be of a boy approximately the same age.
‘Ye know the Kinges grace hath one old fole: Sexten as good as myght be whiche because of aige is not like to cotinew. I haue spied one yong fole at Croland whiche in myne opinion shalbe muche mor pleasaunt than euer Sexten was … and he is not past xv yere old.’
One suggestion is that the young fool was Will Somers who went on to serve Henry VIII (1491-1547) and his successors, and that Sexten (also known by the common fool’s name of Patch) was originally the jester of Cardinal Wolsey, given to Henry VIII as a last ditch attempt to curry favour with the king. See John Southworth’s excellent Fools and Jesters of the English Court (Thrupp: Sutton, 1998), p. 70
Source: Letter from Thomas Bedyll to Thomas Cromwell (c. 1485-1540), 26 January 1535/36, Letters and Papers of Henry VIII, MS Public Record Office, SP.1.101, 152.
Image credit: Oil painting of a boy, Wellcome Collection (CC BY 4.0)