Bay Area Abstract Expressionist painter Robert Pearson McChesney (Mac) did this portrait while aboard ship in the Pacific while in the Merchant Marines and it was in his first solo show in 1944 at Jean (Jehann) Salinger's Raymond and Raymond gallery in San Francisco. Salinger was the mother of JFK and LBJ White House Press Secretary, Pierre Salinger.
This painting can be seen in a photograph of the Raymond & Raymond exhibition, on page 68 "Robert McChesney: An American Painter", self-published, 1996 (ISBN: 0-9650-835-9-4).
McChesney told me that the line of the beard was done with a string, coated with paint and carefully laid on the paper, "printing" the design. He also commented that he was able to complete the work for the exhibition while at sea, with few distractions. He and other artist/merchant marines stayed at a boarding house in San Francisco while at port, preparing exhibitions and socializing. They would then return to sea to paint for their next exhibitions.
The painting is probably a self-portrait, with the jaw line beard and elaborately tied Western style bow-tie, of the type Mac wore in his later years.