When I was but thirteen years of age, a slick haired, befreckled Latino man in a New York Cosmos guayabera approached me on a Metro North train bound for the suburbs, and offered to sell me the deeds to various lands south of the Appellation Mountains.

It was an odd exchange, and strangely tempting due to uncharacteristically low interest rates.  I rejected his offer, of course, knowing all too well that the lands had been sold decades earlier to Thomas Jefferson via The Louisiana Purchase, our country’s finest real-estate deal… I stepped off the train in a state of bewilderment, colored ever so slightly with rejector’s remorse.

The incident had a creeping impact on me.  It was clear this homeless cadger was trying to con what he thought was a naïve trust-fund baby, and had he chosen his target more carefully, someone from Mount Vernon perhaps, he might very well have scored the signature he was desperate for.

Unfortunately, I was raised in Scarsdale, and the 18 percent taxes my parents were gauged out of every year for our Top Ten public school had already paid off.  I knew my History too well to be bamboozled on a railway line.  But I found myself wondering if the man was joking or had really lost his marbles?  And if so, why?  Was he on drugs?  An inch from poverty?  Or had he simply misplaced his little leather marble bag?

I began to ruminate on the correlation between losing ones’ money and losing ones’ mind.  Going broke and going insane seemed to share several characteristics.  Each crisis significantly skews one’s perspective of the world.  Both are framed by denial and delusion, and in an effort to prevent the outcome of either, the subject will take more and more drastic measures.  The question soon became, is the loss of one inextricably linked to the loss of the other?

The answers, I found, were not buried in the case studies of developmental psychology, but on the tongue tips of common sense.  How many human interest stories have been printed about a successful professional who loses his riches in a market downturn only to go postal at the office with an automatic weapon, and return home to do the same to his wife and tropical fish?

Since the creation of representational money, its accumulation has been fallaciously associated with intelligence and rationality.  Some one who cares nothing about money, a poet or artist (i.e. Modigliani: so into his work, he could barely feed himself) is said to be bat-shit crazy, whereas the financier who does the same (sitting in an office 18 hours a day creating nothing), is referred to as “ambitious” or even “eccentric”.

If my initial hypothesis linked financial security with rationality, a contrasting example brought to my attention by the adorable red head in ECON 101 (who was unfortunately dating a dipshit, long distance runner) flipped it directly on its head.

She told me about the case of the well-to-do Wittgenstein family, one of Germany’s wealthiest, over which insanity ran rampant.  Though every luxury was provided for with this family of nine—from chefs, to tailors, to tutors– three siblings committed suicide, and two were plagued by the thought for most of their lives.

Fearing the worst, Ludwig Wittgenstein, a philosophical prodigy, gave away all of his inheritance, and dedicated himself to building railroads for pigmies.  He was considered a wackjob for doing so, but the world of modern linguistics benefited from it immeasurably.  Was giving the money away what kept young Ludwig non-suicidal?

I began to reverse all my conclusions.  Give me the poor, the broke, the dregs of society, I said out loud to no one in particular.  Their disdain for golden shackles will forever serve as fuel for works of great art.

So many artists die without making real money in their lifetime, and how often is their work later heralded as “priceless”?  Our cultures benefit from their lack of conformity, their hatred of the status quo, their indifference towards ostracism or even ridicule, and their innate ability to remain unaffected by the trapping of wealth.

How many painters and composers and philosophers were there throughout the years that could not scrounge enough coinage for something as simple as a decent prostitute– one that would not afflict them with mind eating syphilis– and died as a result, only to be lauded a generation later as men who were not only not crazy, but paragons of creative integrity?  Men and women, who had vision beyond monthly rent checks, and yearly interest, even at their own expense…

Who is crazy?  The person who stumbles through life unfettered in a state of utter fascination, collecting inspirations and returning them through the sensorium of their own creative exegesis?  Or the person trapped in the staid illusion of manicured suburbia and repetitive office life, hording their earnings like greedy black squirrels, giving nothing back but the toxicity of their own entangled cynicism.

It was Michel Foucault who first traced the genealogy of our society’s view of insanity.   Before the Industrial Revolution in Europe, insanity was viewed through completely different eyes.  The Village Idiot, or whoever betrayed the normative values of society, was not restrained in a cinder block institution and medicated beyond recognition.  He was left in the mix of society, and in certain cases, valued as a cipher through which to access non-traditional perspectives.

Is he babbling moronically, an enlightened person might ask, or is that merely what we hear?  With fewer walls up, might we not find some meaning in the gibberish.  At the very least, it’s not more of the same competitive dribble my envious, small-minded, neighbor is gossiping about.  Keep in mind that Shakespeare used the fool to dispense much of the wisdom in his plays.

But as modernization trudged forward, and society demanded that people have an easily explainable vocation, the insane got pushed into the alleyways of society, and eventually, they were institutionalized.  They were not capable of functioning as cogs in the machine, and the last thing the machine wanted were people thinking outside of it, and so, the asylum was built to compartmentalize them.

So, back to this man on the train… Was he talking smack?  Did he believe he was in possession of the deeds of these Colonial lands?  Or… was the whole exchange a metaphor for something beneath the surface?   It is hard to form any conclusion, save the certain inaccuracy of my initial hypothesis.  Losing ones’ money does not always result in losing ones’ mind.

Perhaps that’s why I don’t feel bad about catching up with the man, after exiting onto the platform, and giving him my bastard former mentor’s credit card and social security number.  My former mentor had it coming.  He’d been banging his secretary for years, even had her set up in a loft in the flatiron district.  Life is brutal.  And karma sometimes took too long to set things straight.  So I merely helped it along a bit.

Interestingly enough, my former mentor’s ensuing insanity actually re-corroborated my initial thesis.  His credit card bill was several hundred thousand, and the son of bitch nearly lost his mind.