In the days before the artist Robert Indiana died last May at 89, two of his close associates were brainstorming just what sort of art might be sold under the Indiana brand during his last years.

Maybe people, they wondered, who had enjoyed Mr. Indiana’s iconic sculpture LOVE, with its jaunty, tilted O, would appreciate similar works also based on short words.

What about JOY, one of them proposed in a text message to the other. Or FUN USA? Why not BEER, or perhaps BREW, or even BOB.

There were markets to explore.

“VINO seems to be the biggest that would be the wine drinkers,” Mr. Indiana’s caretaker, Jamie L. Thomas, wrote in one of the text messages to Mr. Indiana’s New York art publisher, Michael McKenzie.