Holbein chose an unusual, nearly square composition for this half-length portrait, a format that concentrates attention on the single point of contact between Cheseman's hand and the falcon's breast feathers. The bird is hooded, its poise entirely momentary, while Cheseman himself looks past the viewer rather than engaging directly, and the dramatic fall of light across his cheek and the pink satin of his sleeve does the work of animating a composition that is otherwise built around stillness and restraint^[1]. It is a picture about a relationship between man and animal rather than a straightforward record of either.

The technical highlight of the portrait is the falcon itself. Holbein achieved the bird's variegated, mottled plumage by dragging his brush directly through still-wet paint, a method that let individual strokes catch and separate rather than blend smoothly, producing a convincingly rough, feathered texture^[1]. That handling sits in deliberate contrast to the flatter, more controlled treatment of Cheseman's own clothing and face, giving the gyrfalcon a tactile presence that pulls the eye toward it even though it occupies a comparatively small part of the composition.

Cheseman is identified as the King's Master Falconer in an inventory of paintings compiled under Charles II, generations after the portrait was painted, but that title has no support from any document surviving from Cheseman's own lifetime^[1]. The royal accounts that would confirm or deny a formal falconry appointment for 1533 are missing, and later account books, which do survive, never mention Cheseman as a royal falconer in any capacity. What is documented independently is more modest but solid: his father's role as cofferer to Henry VII, and Robert's own public function as the king's representative in Middlesex, along with his presence in the 1540 delegation sent to meet Anne of Cleves on her arrival in England.