Rosenberg was often unable to afford models and his oeuvre includes many self-portraits. The earliest are slight and delicate in the melancholic Romantic tradition of Benjamin Robert Haydon’s portrait sketches of the young Keats. Between 1912 and 1915, however, under the influence of the Slade, Rosenberg began to shed this persona in a series of leaner, bolder self-portraits which display a new bravura confidence and mark his transition to modernism. Unsentimental, yet poignant, this is Rosenberg’s final self-portrait and completes the series; it is also his final finished work as a painter. Drawn in gouache and chalk on crumpled, poor quality brown paper, possibly salvaged from a parcel sent from home, after Rosenberg had been sent to the Front in Northern France, its fragile state documents this important part of its history. The portrait appears to relate closely to a sketch made in a letter, entitled Self-portrait Sketch in Tin Helmet (c.1916, Imperial War Museum) of which Rosenberg joked to his family that it was ‘The New Fashion boiler hat – the trench hat’. These hats or steel helmets were issued in June 1916 while the troops were in billets prior to their first experience of trench warfare and most probably the gouache portrait was created at this time.

Rosenberg was killed while on patrol on 1st April 1918 at the age of 27. Despite publishing only two short collections of poetry during his lifetime, Rosenberg is now regarded as one of the finest War Poets of his generation.