“Who is the greatest thief in history?” is one of the most provocative party questions I’ve ever heard. As usual, the most provocative questions earn their mettle not in the question asked but in the answers. Some of the early answers, from the party goers, focused on the monetary value of the theft(s). If one thief stole $6 million dollars worth of currency and/or products, and another stole $7 million, then thief B was obviously more successful. That statement is not wrong, of course, but it doesn’t carry a lot of provocative value.

Others qualified their answer with media and historical value. “Thief B may have stolen something of greater value,” they said, “but if we are obviously more fascinated by thief A, calculated by the number of news stories written in their present tense, and movies and documentaries written posthumously, then you would have to say that thief A is more famous and thus more successful.”

Neither of these answers are wrong or right, but such is the nature of provocative party questions. We love to debate, argue and discuss trivial issues that have no bearing on anything consequential. Our answers define us, and most of us deal in answers that lie somewhere below the bottom line: More fame equals better, and/or more money equals better. It’s human nature for most of us to try to cut through the fluff and find an inarguable answer. Bottom line, it’s fun to debate.

Every once in a great while, someone comes along and shuts the floor down. They say something to which there is no argument. We can’t argue the merits of fame, in other words, and arguing over total value is kind of pointless when someone who truly knows the facts of the value of the heist(s) thief B masterminded, but we could argue that those arguments are not provocative, in lieu of the answer one of the party goers offered for our consideration.

“We all want to be rich and famous, and thieves are no different, but the overwhelming desire of an accomplished thief should be to avoid unwanted attention, particularly when it leads to a level of notoriety or infamy that might lead to their incarceration. The answer to your question is that we all have an opinion on who the greatest thief of all time is, but what are those answers based on? They’re based on reporting, in the media and history, but I submit to you that we probably don’t know who the greatest thief of all time is, because law enforcement was unable to catch them, the media didn’t report on them, and they essentially remain unknown to history. The reason I consider this theoretical answer perfect, is that I knew a skilled thief, and I saw everything he fell prey to in his formative years. He turned out to be the opposite of a skilled thief, because the relative elements of fame, relative to our little corner of the world, and greed caught up to him. The theoretical greatest thief of all time would learn to avoid these pratfalls, that minefield, or those treacherous waters, and lived out the life of the greatest thief of all time.”

***

Retired law enforcement officials inform us that the crimes that still keep them up at night are the random, or seemingly random, crimes that were almost impossible to solve. Law enforcement officials count on a number of factors to help them solve such a crime, but the most prominent ones involve the character flaws inherent in the criminal mind.

One of the more intense scenes of Martin Scorsese’s Goodfellas involves the actions of the players involved in the Lufthansa heist. This scene is based on a true story, and in the true story, as in the movie, the main player instructs the players involved not to spend the money to draw unwanted attention. Some of the players go out, in a relatively short span of time, and defy that order. “How could you have been so stupid?” the main player asks. To which, those of us in the audience say, “How could you have been so stupid to include this player. You knew who he was in the planning stages. Why did you include him in your plans?” The answer is that if you plan on engaging in a large heist, you’re going to have to hire some thieves to help you carry it out, and thieves have the thief’s mentality.

Most criminals have never had any real money. If they grew up with money, inherited it, or found their own honest way to make real money, they probably wouldn’t be thieves. Thus, when they manage to successfully steal some money, most of them will not invest it in slow growth, high yield municipal bonds. They’ll spend it with the same impulses that drove them to steal in the first place. They’ll spend it to try to live the life they thought they should’ve been living all along, they’ll spend it to live the life they think others live, and they’ll spend it in a manner that draws unwanted attention. They have never had any real money, so they do not know what to do with it when they get it. Thieves also know they’re living on borrowed time, so they spend their money as if it will all end tomorrow.

Buying extravagant items leads to extravagant flaunting, and flaunting leads to talk. Their people may not speak directly to law enforcement officials, but talk leads to talk. If the thief displays some restraint in this regard, they are apt to fall prey to another human conceit of wanting to tell those who said that they would never amount to anything in life about their newfound wealth. The natural byproduct of those forced to endure the bragging is jealousy, and jealousy might lead to trusted friends and family making anonymous calls that can change the direction of an investigation. In the event that those with a thief’s mentality are able to avoid the typical pratfalls of criminal success, law enforcement officials will often sit back and wait for greed to take hold.

If a true piece of work (a POS) manages to pull off a $10,000 heist, $10,000 dollars will not satisfy a thief. The nature of the thief’s mentality –as taught to me by Kurt Lee­– is such that they will probably be planning a $20,000 heist in the getaway car. How many of us have watched a movie, read a book, or known a true POS in life and said, ‘If they would’ve just stopped at some point along the way, they could’ve walked away with all that money. How much money did he truly need?’ Kurt Lee’s mentality suggested to me that it is about the money, and it isn’t. Money, wealth, and comfort drives the heist, but no amount of money can satiate that drive. A true POS has so much wrapped up in those heists that they eventually fall prey to all of above, with greed being the most prominent.

***

I knew Kurt Lee, on a superficial level, for years. He was good friends with my best friend. Kurt Lee and I spoke just about every day for years, but we were never so close that one would characterize us as intimate. It wasn’t until Kurt Lee invited me, and my best friend, to join him at the baseball card shop that I received a window into Kurt Lee’s mentality. As detailed in the first installment of this series, by the time Kurt Lee and I were in the car driving over to the baseball card shop, shoplifting had long since lost its thrill for him. It bored him so much that he asked me if I wanted to watch him steal from that baseball card shop’s owner. I never met a true thief before Kurt Lee, so my reference base was limited, but I imagined that more experienced thieves would suggest that this was the on ramp to a bad road for Kurt Lee.

More experienced thieves might also suggest that the very idea that Kurt Lee was attempting to accentuate the thrill of theft, by having another watch him do it, suggests that Kurt Lee wasn’t motivated by what they might call the philosophical purity of theft. He wasn’t doing it to balance economic equality, in other words, as some more experienced thieves will say to convince themselves that there is nothing wrong with stealing from someone that has so much that they don’t know what to do with it anymore. He wasn’t doing it to put food on a table, or any reasons that a more experienced thief might consider a more noble or justifiable motivation. Kurt Lee was simply doing it because he wanted the stuff on the shelves, and he enjoyed the thrill of it all. Once that thrill was gone, he needed to supplement it. A casual observer, just learning of Kurt Lee, might also suggest that he asked me to watch to quell some deep seated need he had for approval or acceptance. I would’ve considered that notion foolish at the time, for the Kurt Lee I knew displayed no visible signs of caring what anyone thought of him, much less me. With the advantage of hindsight, however, I have to consider that a possibility.

The young man I knew believed in the spirt of generosity, but the basis of his belief in it was conditional. These words came out of his mouth most often when someone had something of excess that he wanted, yet I witnessed a number of generous acts on his part. I saw him help out our fellow students in need, and he helped me. Yet, his generosity was more of a quid pro quo than it was a simple act of generosity born of altruism. When he asked others to engage in the spirit of generosity in turn, the initial recipient of his previous acts of generosity often paid about four times what his generosity cost him. After the first, and only, interaction in this regard, I decided it was better for all concerned that I go hungry rather than ask him to lend me lunch money for a day.

He claimed that his generosity was pure however, and he enjoyed it when others considered him a generous man, which leads me to believe that if the adult Kurt Lee managed to pull off a $10,000 heist, he would begin spreading the wealth around. He might hire the services of a prostitute for a night, he might give some of his newfound largess to a homeless person, or he might generously tip a waitress or a housekeeper, and he would do it in a manner that would lead people to talk. He would spread the wealth around just to be a guy who could, for one day in his otherwise miserable existence. He would do it with the hope that his various acts of generosity might say more about him than the criminal act he committed to attain the money. His motivation for sharing would not be truly altruistic, in other words, and he would do it regardless if he considered the idea that these actions might lay some breadcrumbs for law enforcement.

The point is that the theoretical greatest thief in history we talked about at the party, one presumably imbued with the same thief’s mentality as Kurt Lee, wouldn’t fall prey to any of these conceits. The point is that this thief would be such an exception to the rules governing one with a thief’s mentality that he might be able to achieve something historic in the field of criminality.

***

Those of us who knew the as of yet unformed, maladjusted, high school-era Kurt Lee wouldn’t need the prophetic words of a skilled thief to know where Kurt Lee would end up. We also didn’t need the list of fatal flaws from law enforcement officials to know that Kurt Lee was susceptible to falling prey to these conceits. Especially after he became the center of attention in high school.

Someone at our school learned about Kurt Lee, and they spread the word. I didn’t know who they were or what they said the what this person said to spread the word, but I have to believe that it had something to do with the idea that for everything was, he was not a nice guy. People often say the worst things they can think up, then they clean it up at the end by saying, but he’s actually a really nice guy. My bet is that with Kurt, they concluded with “Far from it. He’s actually a real piece of work (a POS).’ For most of those outside our demographic, I imagine that such a presentation might do some damage to Kurt Lee’s brand, but for us it was a special résumé enhancer. If Kurt’s carnival barker told the fellas around him that he found a guy that was dishonest, duplicitous, and something of a POS, but he was actually a pretty nice guy, the air would leave that expanding balloon. Most of us are already friends with nice guys, and our dads and our uncles are nice guys too. We want something different, some conniving, unpredictable, POS who shocks us.

Whatever the carnival barker said to describe Kurt Lee clicked, because Kurt Lee ended up becoming something of a celebrity in some quarters. The top athletes at our school were dying to know what he was going to do, or say, next. They thought he was hilarious. The cool kids even stopped by to get Kurt Lee’s reaction to the latest events of our school. They had never seen anything like him before. He was like a real life Al Bundy in our midst. Those of us who tried to avoid thinking that such people were impressive couldn’t believe the attention Kurt Lee was getting. Kurt Lee couldn’t believe it either, and he also didn’t understand it.

Those of us who witnessed this, learned what an unusual attraction those in our peer group have to a true POS with a thief’s mentality, and I don’t make any claims to being immune to this. As the previous entry suggests, I found Kurt Lee fascinating and hilarious. Some may consider it a bit of a stretch to suggest that the young, unformed male mind wants to witness a bully humiliate and hurt others, but if it happens most young males want to be around to witness it. Those who told Kurt Lee’s stories knew that no one enjoys hearing a story from a guy who can’t stifle his laughter, so they managed to get through their narrative without laughing. It was hard though, because the vicarious thrills one receives from telling such a story can be difficult to maintain.

Kurt also, incidentally, opened a wormhole to our understanding of what it took to be an honest man. He was so unabashed in his dishonesty that some of us considered him the most honest guy we knew. He was a genuine article of consistent, and unflinching, dishonesty. When Kurt Lee learned that these aspects of his personality appealed to a wide swath of fellas our age, he exaggerated these characteristics in a way that suggested he didn’t understand their appeal any more than we did. His answer to whatever dilemma plagued him was to try to live up to the caricature that we built for him and exaggerate it.

Kurt Lee became that bully, thief, and POS that every young, unformed male dreamed of being but dared not stretch to the point of extremes. The problem for Kurt Lee was that he needed a victim who would allow him to display his characteristics without consequences. He chose to focus on those inferior, non-confrontational, and significantly smaller than him, so they would present no challenge. He openly challenged anyone he considered at the bottom of the food chain to bolster his POS profile for those in attendance.

Kurt Lee was a POS the day I met him, but prior to his brief taste of popularity, he displayed a bit more discretion. I don’t know if he didn’t want to get in trouble, of if he actually had limits, but once he discovered how much the athletes and cool kids loved whatever it was that he was, he was balls out.

The problem with becoming such a character is that, inevitably, an ugly truth will rear its head. Young, unformed males eventually grow bored with a consistent character no matter how consistently offensive and insensitive that individual may be. When that happens, the instinctual response of such a character is to up their game even more, and exaggerate those unacceptable characteristics that everyone loved fifteen minutes ago, until the character ends up doing it so often, and to such excess, that he ends up revealing his desire to be accepted. This new game face stood in stark contrast to the very characteristics that made Kurt Lee so appealing in the first place, to those in the upper caste system of high school. It also resulted in the implosion I alluded to in the first installment.

This implosion started when something went missing in our school. Kurt Lee plead innocence, on numerous occasions, claiming that he was being unfairly singled out by our school, and he may have been, but Kurt Lee made a name for himself for all the wrong reasons. He may have been such an obvious suspect that he was too obvious, but the school ended up expelling Kurt Lee as a result.

If Kurt Lee permitted me to caution him, prior to this incident, I would’ve informed him that these athletes and cool kids don’t give a crap about you. They may like you in the short-term, as they take what they want from you, in this case entertainment, but once they have expended you as a resource they will put you out at the curb. They don’t care if you’re an actual POS, or if you’re just playing that character well. They don’t care if a person wants their attention. They won’t pay as much attention to them as they did fifteen minutes ago, once they see through the veneer. This long-term view would not have mattered to Kurt Lee however. He wanted to bask in the glow. When that brief spell ended, it wounded Kurt Lee, and he attempted to up his game even more, until he ended up with an expulsion, and he eventually ended up being incarcerated for another, unrelated matter.

***

Decades later, those of us who went to school with Kurt Lee were all standing around a funeral engaged in a ‘What ever happened to’ conversation regarding our old classmates. Kurt Lee’s name eventually came up. Laughter erupted at the mere mention of his name, as we all remembered the awful things he did to people. Someone in our group attempted to quell that laughter by mentioning that he thought Kurt Lee was actually a pretty awful person. No one said a word. That silence occurred, I can only presume, because everyone considered that characterization so obvious. Another spoke about Kurt Lee’s expulsion from our school, and the subsequent incarceration for an unrelated crime. Those who didn’t know about the incarceration laughed when they heard about it, but it wasn’t the bitter schadenfreude that often comes from those who were bullied, ridiculed, and beat up by the guy in high school. The laughter was more of a head-shaking chuckle that suggested we all knew that’s where Kurt Lee would eventually end up. Then the subject changed, and it didn’t change because some of those, at the gathering, harbored ill will towards Kurt Lee, and they wanted to move on in life. The sense that they had already moved past all that was palpable. The subject changed because no one truly cared what happened to Kurt Lee.

If he was a celestial being, witnessing this conversation, with the ghost of Christmas past over his shoulder, he may have offered a number of excuses for why people thought he was so awful. He might inform the ghost of Christmas past that he was just a dumb kid at the time, and he might have said something about how bullying actually prepares kids for the real world in that it strengthens their constitution against future bullying. Kurt Lee might have experienced a slight twinge of guilt, hearing our accounts of him, but I don’t think so. I think he would’ve enjoyed hearing us talk about him. Seeing how quickly we changed the subject, however, and all that it intoned about how we felt about him long-term, probably would have stung.

The fundamental mistake Kurt Lee made, a mistake that most of us make at that age, is that we know nothing about human nature. We don’t understand how few people truly care about what happens to us, and we fail to grasp that nothing –including internal squabbles, politics, and the desire to be more popular– should keep us from these people. The mistake we make occurs when we seek the approval of others, because we often direct that effort at those who don’t give a crap about us in any kind of comprehensive manner. Kurt Lee made the fundamental mistake of believing that when those cool kids began laughing at the things he did that they were laughing with him. He made the mistake of believing when others are interested in what he had to say or do, they     are interested in him, and I can only presume that when these truths became evident, he attempted to double down on those characteristics they enjoyed, it ended up destroying him from the inside out.

As evidence of this, one of the members of this conversation knew some things about the adult, post-high school Kurt Lee. He told a couple of stories about how Kurt Lee began stealing bigger and better things more often.

“He didn’t learn his lessons from high school,” this storyteller informed us. “He grew so bold that one could call some of the things he did stupid.” Some may place whatever it was that drove the adult Kurt Lee to steal more expensive items, at a greater rate, under the umbrella of greed, but I think it goes much deeper than that. I think that expulsion, and the end of the life he once knew, drove him to neglect those mountain lion skills he often displayed by refraining from launching on his prey, until he could determine that there was absolutely no chance of any harm coming to him. The stories I heard, that day at the funeral, of Kurt Lee stealing such conspicuous items were so confusing that I couldn’t help but think they were troubling and obvious cries for help.

Kurt Lee was the best thief I’ve ever known. He was, of course, a small-time thief, and if he could’ve maintained that small-time status, I thought, he could’ve walked away from it all. If the greatest thief of all time were to fall prey to some of the same things Kurt Lee did, in his formative years, that thief would have to learn the lessons from these formative years. Kurt Lee, obviously, never did, and the fact that he ended up doing time suggests that the adult, post-high school Kurt Lee didn’t either. It suggests that he eventually imploded under the weight of whatever he was when I knew him.

The final answer to the provocative question is that there probably is no greatest criminal that the media and law enforcement never knew, because no criminal could engage in various acts of criminality with a sound mind and a guilt-free heart. The various taints on their soul are what drive to commit acts of theft and violence, and those taints and blemishes do not heal with one simple band-aid.