[1][2] Simon received his B.A., M.A., M.Phil., and Ph.D. degrees, all from Columbia University,[3] where his doctoral thesis focused on Bronzino’s portraits of Cosimo I de’ Medici.
[1] In 1997, he sold a watercolor by Richard Dadd and opened an art gallery on Upper East Side.
[2][7] Simon has been described as part of an elite group of curators and dealers, known as the "eyes," who carry a unique instinct that can distinguish authentic paintings from copies and spot lost treasures.
[8] In 2005, Simon, with his friend and colleague, art speculator Alexander Parish, acquired Da Vinci's original Salvator Mundi, then thought to be lost, from a New Orleans auction gallery for $1,175.
[9] He brought the painting to New York University professor Dianne Dwyer Modestini for a detailed restoration, and sent it to numerous scholars for verification that the painting had belonged to Da Vinci, including Metropolitan Museum of Art curator Keith Christiansen and National Gallery director Nicholas Penny.