This modest sculpture is Rogers' final "published" group, that is, the last work he created for mass distribution. Released in 1892, it commemorated the four-hundredth anniversary of Christopher Columbus's discovery of America, which was to be celebrated at the World's Columbian Exposition in Chicago the following year. At 15 1/2 inches high, it is relatively small compared Rogers' works from the previous decade. As Rogers often did for his theatrical and literary subjects, he provided a lengthy text describing the dramatic moment on the flagship Santa Maria captured by the sculpture. "After a tedious voyage, signs of land were noticed for several days, and on the evening of October 11 they became so numerous that no one slept, all being on the watch for the first sign of land. About eight o'clock that night, Columbus, from the 'Santa Maria,' saw a light which repeatedly appeared and disappeared. He could scarcely trust his own senses, and called two of his officers to confirm the discovery. One of them saw the light, but the other did not." Rogers placed Columbus at left, pointing into the distance. His two officers follow his gaze; one leans forward with an intense expression, straining to see the tantalizing flicker, while the other stands erect with a look of dawning recognition, having seen the light that will soon prove to be land. Rogers' oeuvre encompassed a variety of themes, including the Civil War groups that established his fame, genre scenes of everyday American life, and subjects taken from popular theater of the day. This final work represents a historical event, a subject traditionally classed among the loftiest themes an artist could depict. Rogers had pursued such themes during his late career without the success he had hoped for. As early as 1871 he had made designs for a large Revolutionary War sculpture that he called "Camp Fires of the Revolution," but it was never carried out. In the late 1880s he attempted other designs for monumental sculptures that also did not come to fruition, including "John Eliot Preaching to the Indians" and the "Stamford Memorial," which celebrated the purchase of that Connecticut city's site from the Indians in 1642. In this final work he realized a historical subject, though in the small format for which he was best known. After a successful career of more than thirty years, in the early 1890s Rogers began to suffer from difficulties with his hands, and his chronic eye problems worsened. Just a few months after completing The Watch on the Santa Maria, the artist announced that he had sold the rights to his groups to William Brush, longtime foreman of his plaster shop. The subsequent Rogers Statuette Company was short-lived, publishing its last known catalogue in 1895.

Benjamin Franklin brought back from France seven replicas of this bust to present as gifts to friends. The original bust, signed and dated 1777, is in the Bibliotheque Mazarine in Paris.

Laura Derby Rogers was the daughter of John Rogers, the sculptor, and Harriet Moore (Francis) Rogers. She was the sister of John Rogers III and of the donor.