After Lisa's new guinea pig chews a hole in the family's iconic sailboat painting, the Simpsons go shopping for a new painting. Marge finds a landscape painting at the Van Houten's garage sale, and they purchase it for $20. Shortly thereafter, the family discovers it was painted by a famous artist and is worth at least $80,000. Marge wants to split the money with the Van Houtens, but Homer convinces her not to.

Unfortunately, Milhouse overhears their discussion and tells his parents. The Van Houtens tell Kent Brockman and soon the whole town is divided over the issue of the painting. Kirk's old girlfriend (from his split with Luann) says she is the real owner of the painting, and Homer visits Isla Verde, where Kirk purchased it, to prove she did not buy it. Homer confirms Kirk bought it, but also that the painting is a forgery. He has the forger draw two paintings for him: one to bring the Van Houtens back together and another to replace the old sailboat painting.