Compared with more idyllic, sentimentalized representations of youth, William Winner's News Boy is unusual for the subject's individuality and depth of expression. With his resigned pose, knowing gaze and tattered clothing, Winner's subject appears fully aware of the tumult and hardships of the day.

Given the attitude of an observer, the boy differs significantly from 19th century images of children who remain free and uncaring of the world around them. With the backdrop of monumental pillars and civil war soldiers and with the year 1864 boldly painted on the box beneath him, Winner's News Boy approaches social commentary and America's lost innocence in the wake of war.

William Winner was born in Philadelphia around 1815, and few facts are known about his early life.

He began exhibiting portraits at the Pennsylvania Academy of the Fine Arts and the Artist's Fund Society in 1836. A genre, portrait, historical and religious painter, Winner was elected a member of the Pennsylvania Academy in 1860. He was also a frequent exhibitor at the Boston Athenaeum, Apollo Association, American Art Union and National Academy of Design.

William Winner's works can be found at the Wadsworth Atheneum Museum of Art, Corcoran Gallery of Art, George Walter Vincent Smith Museum, University of Michigan Museum of Art, Pennsylvania Academy of the Fine Arts and the Philadelphia Museum of Art.