Michael Clapper of Franklin & Marshall College has noted, "Eakins’s choice of [chess] and his knowledgeable treatment of it suggest that he was familiar with and interested in the game, though there is little direct evidence of it apart from the painting.

"[1] Art historian Akela Reason proposes that the painting is a tribute to a number of the artist's father-figures: Holmes probably was Eakins's first art teacher; Gardel was his French teacher; Benjamin Eakins was his literal father; and Jean-Léon Gérôme, his master at the École des Beaux-Arts, is represented by a print of Ave Caesar Morituri te Salutant, over the clock.

[2] Author Martin Berger has analyzed the content of the painting in detail, finding it an evocation of the passage of time and ascribing it a highly personal meaning in Eakins' life.

In the way that his father Benjamin is placed in opposition to Eakins the painter, the two may be envisioned as playing out a psychological "conflict" across the other axis of the chess board.

Although the painting was dedicated to Benjamin, the title "The Chess Players" curiously leaves Eakins' father out of the narrative of the picture.