Like the Penrose family, the artist who painted this portrait of The Postman was no stranger to controversy. Born in Dublin in 1769, Martin Archer Shee studied art at the Dublin Society´s Drawing Schools. He then moved to London, pursuing a successful career as a portrait painter. Shee was also a talented poet and playwright, and in the 1820´s his play Alasco was banned for advocating Republican principles.

This however did not prevent Shee´s election, in 1830, to the presidency of the Royal Academy. Shee´s portrait of James Penrose, painted around 1806, shows the young man dressed in classic Regency style, with ruffed lace collar and red velvet jacket. The painting depicts James as a dashing Byronic figure, rather than a conservative businessman, and this is in keeping with the perception of
the Penrose family in the city of Cork at that time.