Underwood then agreed to raise money for a Confederate monument in Richmond, Virginia. However, the project was embroiled in legal controversies which ruined him financially and physically. In 1910, oil portraits of many of the twenty Confederate generals he had commissioned from E.F. Andrews were auctioned by a Covington, Kentucky warehouse to pay storage fees, and most ended up in Virginia. By that time, Underwood's wife had died and he lived in Manhattan, New York and described himself in the census as an author.