It is believed that the original owner of this Duesenberg was Rowland Rich Woolley, a prominent Hollywood attorney known for representing many of the film industry’s most recognizable stars. His client list included Mary Astor, Olivia de Havilland, and both Lionel and John Barrymore, placing him among the most influential entertainment lawyers of the era.

Woolley also represented Lydia Knott Grey, who famously received what was considered the largest divorce settlement in American history at the time, awarded during her separation from Charlie Chaplin. According to long‑standing speculation, Woolley’s substantial fees from that high‑profile case may have helped finance his purchase of this Duesenberg, an acquisition perfectly in line with the glamour and extravagance of early Hollywood.