Henri painted Skipper Mick, a portrait of the Irish boy Jimmy Michael Macnamara, on October 24, 1924. It was probably executed on Achill Island, off the Western coast of Ireland, where the artist had a home, Carrymore.

During his journeys in America and abroad, Henri painted children, often those of varying races and nationalities, for he saw them as individuals who transcended international boundaries. The artist wrote: "Every nation in the world in spite of itself, produces the occasional individual that...expresses...something of the dignity of life, the humor, the humanity, the kindness...that will rescue the race and the nation." (Henri, pp. 111-12) Certainly the image of Skipper Mick evokes this sentiment.

Henri enjoyed capturing life around him, and it is not suprising that he would choose such a lively subject, with his jaunty cap and air of savvy, conveyed by his stance and hand stuffed in his pocket. The artist probably finished the portrait in one sitting, believing that quick work allowed for easier representation of the fleeting gestures that communicate insight into the character of the sitter. Through his broad brushstrokes and colorful palette, Henri has superbly captured the vitality, dignity and what he termed the "the tremendous activity of a boy sitting still." (Henri, p. 195)

This portrait is listed in the artist's record book M as no.193 and was once owned by the well known collector Francis P. Garvan.