'Lester' — Lester Reiff, Jockey

Ward's plate captures the American jockey Lester Reiff in full working dress: long tan overcoat, white breeches, tall black boots, and a pale flat cap. He leans lightly on a riding crop, body angled forward in the slightly hunched silhouette Ward favoured for sportsmen. The caption reads simply 'Lester'. Reiff, then at the height of his English career, had won the 1900 Derby on Volodyovski and was a transatlantic sensation. Ward's caricature exaggerates his lean frame and sharp, jutting profile without ethnic distortion — notable given that American jockeys of colour faced virulent press caricature in the same era. The image reads as sporting admiration, positioning Reiff as a cool professional rather than a social curiosity.