I want a criminal. The higher profile the better. I’m assembling subjects for an exhibition of portraits at a gallery in New York. Rather than just the usual suspects–family, friends, art world types, I want someone bad. I see the exhibition as a sort of dinner party where the guests are a crazy mix. An ex-con sounds good to me!

Jacques Mesrine (left), played by Vincent Cassell in Jean-François Richet's recent film "Mesrine"

The economic crisis and bank bailout are all over the news. Who better than a Wall Streeter with a Hollywood pedigree? Ivan Boesky! The first of the big insiders to go down in the 80’s and the model for Gordon (“Greed is good!”) Gecko in Oliver Stone’s “Wall Street.”

Michael Douglas as Gordon Gekko

I learn that, like me, he’s from Detroit and went to the University of Michigan. When his ambitions were too big for the Motor City, where his parents owned a Russian deli we used to go to called Boesky’s (bo-ES-keys back then), he left for New York. Graduate school at Pratt Institute was my lure.

Boesky's Delicatessen, Detroit

Wall Street worked out pretty well for Ivan. He even donated $20 million to the Union Theological Seminary for a new library. And then the axe fell. Prison, divorce, Oliver Stone. Who do you become after all that, and how is it revealed through one’s response to art? What painting, I wonder, would he fancy looking at with me at the Met, or perhaps at the Getty in LA; I hear he’s living in La Jolla, nearby. Now years after he served his time, what might he say to priceless paintings by Rembrandt or Vermeer, or Hubert Robert?

Hubert Robert, Hermit Praying in the Ruins of a Roman Temple, 1760, Getty Museum, LA

I write Ivan a pitch letter, including this paragraph:

Yes, you committed a crime. And yes, that interests me as someone who tries hard to do the right thing but doesn’t always, but also as a Jew from Detroit, an alumni of the University of Michigan, and someone drawn to NYC out of his ambitions. Obviously, you are more than the crime you committed and paid for, and it is that whole person who I am interested in portraying in a portrait. Twenty three years later people on Wall Street are getting rich off ever more sophisticated scams. Seems like a good time to think again about Ivan Boesky, maybe from a new angle. Yours?

But where to send the email? I google. Lots of breaking news items from the 80s, the 90s, then the trail goes cold. I email the director of a Chelsea gallery owned by his daughter, Marianne Boesky. No response. Marianne herself. Ditto. I write friends from Detroit, including one with vaguely criminal connections, hoping for old family ties. Nothing.

Even in the age of Facebook, if you want to hide, no problem.