Norton Simon was a unique collector because he let passion guide his collecting interests, but he controlled his passion by making his purchases based on smart economic decisions bolstered by years of experience in successful business negotiations. The Norton Simon Museum, today in Pasadena, California, displays the eccentric collectors life work as he created one of the greatest and most recognized collections on the west coast. By examining the progression and establishment of Norton Simon Inc., alongside the creation of the Norton Simon Art Foundation, multiple parallels can be drawn between Simons’ unique approach to business and the application of his unorthodox techniques to his purchases in the art world – Norton Simon’s “two hats”.