Mr. O´Leary was highly suspicious of acts of kindness. He had been working in a field – contract law – where nothing ever was what it first seemed to be. As a lawyer he had had to train himself to question not just every contract presented to him, but to question even the expressed will of every client who came to him to have a contract drafted.
This was kind of the connecting negative puzzle piece to the legal plain-meaning rule, a principle used by courts in interpreting contracts that provide that the objective definitions of contractual terms are controlling, irrespective of whether the language comports with the actual intention of either party.
Mr. O´Leary was a specialist in creating contracts that satisfied plain-meaning-interpretation, eliminating inconsistencies and double-meaning phrases, extracting the literal content of the contract from the hidden intention of his clients without making it plain that other than purely legal and contractual reasons were actually motivating his clients to sign a contract that was written thus.
His guiding principle in understanding the lawyer-client relationship was that clients expected him to know about them and their intentions without telling him, in fact, for him to know what they could have known about themselves but preferred not to know and thus would not relate to him in plain terms. He considered it his job to shield them from this kind of painful, self-reflecting knowledge and he was supremely certain that his clients expected him to not ever let them know what they preferred not to know about themselves but to keep it disguised from them while at the same time adjusting the contracts to their hidden goals thus allowing them to continue to feel – reasonably – good about themselves and at the same time satisfy – and justify – their true goals.
When he was a young lawyer still – and green with it – he executed – to the letter and in an irreproachable manner – what clients told him to do and wondered when they paid their bills without complaint and still carried their business elsewhere afterwards. But he was quick on the uptake and soon adjusted his business conduct. There were certainly things they did not teach you at law school. Ever since he´d adjusted his guiding principles , clients, high paying clients, knew how to find him even though he was literally hiding amidst his file boxes like the Minotaur at the heart of the labyrinth Daedalus designed.
A graduate and scholarship student of the University of Chicago Law school Mr. O´Leary in his day had had his choice of law firms who´d have been glad to consider his application. He was extremely smart and had an impeccable work ethic. He´d also been subject to the same prep-talk (he called it propaganda) of „success“ as his class mates. Judged by how their alma mater described her alumni they all were but a group of friends who would pick up the phone anytime one of them called with a question and sat down with him to walk through issues. According to their law school they all were extremely fun, thoughtful, smart, and FUN students, and would continue to bring the same energy to their work as lawyers.
It was not that he did not appreciate the excellent education and rigorous academic training he had received.He also knew that the average salary for newly minted law graduates was nearly about $180,000 per year by now and that the graduates were worth it. It meant that as a lawyer with no experience he could have immediately be in the top 5% of U.S. earners. But for some unfathomable reason he also knew that students graduating from a top tier law school were the same as people on average with the only – significant – difference that they were subject to more diversion and temptation.
He did not graduate top of his class to be diverted from life. He could have taken three or four top performing associates from any top law firm and founded his own big law firm as a naming partner. It was all within his reach. But it was not what he had wanted.
If it seemed strange to others that he had accepted Mr. Letterman´s offer to become a partner on 35th street rather than to join one of the top ten law firms in New York and get worn down as an associate there before being hired by an excellent law firm and becoming partner eventually it was because they did not know some of the things about him, he thought he had realized early on.
It was not a sign of humility that he had chosen Mr. Letterman sen. instead. It was not exceptional that he did not get drunk on the prep talk of success. He had not been a recluse in law school. He had actually differed from the other highly motivated graduates and future pilars of society in a degree up, not down, by a notch. He had wanted more. It had been an extreme act of arrogance and late-puberty idealism (the same) and the result of careful research. He had been very clear to himself about what he thought he wanted and what he thought he did not want.
He was convinced back then – and was convinced still – that life mostly just happened to people, even or especially people who graduated from top tier law schools. Even early on in law school, he was convinced that people wasted about 15 – 20 years of their lives and took another ten to rectify their initial mistakes, if they were so lucky to live as long as that. He was not going to be cheated by life in this manner.
Mr. Letterman had an excellent reputation. You did have to know how to find him. The office address was not sufficient to get in touch with him. But Mr. O`Leary was a good observer. Mr. O´Leary had also been told that Mr. Letterman sen. was legend and did not accept any applications. He had been told that even if Mr. Letterman would accept an application, he´d be likely not to pay the kind of salary that a University of Chicago Law school graduate legitimately could expect as a starting salary. This was concluded by the state of Mr. Letterman´s cramped office and filing system.
But what mattered to Mr. O´Leary was something fairly abstract and elusive: he was convinced that Mr. Letterman was one of the few lawyers he´d ever encountered who was in charge of his own life. His research showed that nobody took Mr. Letterman sen. along for a ride. As Mr. O´Leary saw it, Mr. Letterman owed nobody a kindness. He certainly did not owe him, a recent graduate, an opportunity to reach out for the kind of life he thought Mr. Letterman had found. He knew though he was depending on an act of kindness for Mr. Letterman to accept his application.
Not that he believed in it. In kindness. He had been practicing law for many years now and he had lived in NYC for as many years and he was sure, absolutely sure, that he had never encountered a genuine act of kindness apart from Mr. Letterman´s willingness – as many years ago – to accept his application.