Look, we were the Chief Justice of the Supreme Court of the United States, we get it, but the City of New York has too many damn (not my first choice swear word) lawyers. The City’s Law Department has a thousand lawyers. You read that right. And each agency also has its own legal department. We would doubt that the City even knows how many attorneys it has filling attorney positions (and the position we occupied, was a managerial, non-legal, position, as we were frequently reminded by our legal colleagues). There are about 60,000 lawyers practicing today in New York City (it was much more pleasant when we started practicing in the 1760’s and there were only a couple of dozen of us. Even Aaron Burr, wasn’t that bad a guy). Let’s say there are 2,000 lawyers working for the City – that’s over 2% of the total number. And the City tends to lose. For example, the City paid out over $600 million in tort claims in 2019 alone. That’s a crazy number.

            There are and have been some tremendously talented, dedicated and productive attorneys working for the City. Len Koerner, who was, for many years, the City’s chief appellate lawyer, was the most effective legal advocate it has ever been our privilege to observe in court. Working without notes, Len’s command of the law (and ability to cite particular cases) and deft ability to respond to judicial questioning were remarkable. He admirably represented the City for decades. We have worked with attorneys with expertise in real estate, telecommunications, condemnation, zoning and housing law, for example, who are/were the top practitioners in their respective fields of expertise and who were deeply dedicated to public service. 

            But the culture of the Law Department is bizarrely dysfunctional and given the number of attorney positions and the City’s limited ability to compete in the market for legal talent, there are a lot of simply not very smart people practicing law in positions of responsibility for the City. While the Law Department and its chief, the Corporation Counsel, are, in theory, the City’s lawyers, the institution of the Law Department, has its own interests which often trump those of the City’s legal, financial and policy interests. But on legal issues facing city government is the last and final word. 

            City attorneys travel in packs. It is impossible to go to a meeting in City government where legal questions are at issue where fewer than two attorneys are present. Often there can be as many as ten. And City lawyers frequently complain that they are understaffed. If they sent half as many bodies to meetings and shortened the length of those meetings by half, they would quadruple their output. The large numbers of lawyers at big meetings are the result, in part, of the expertise within the City’s legal cadre being sliced razor thin, as well as no one’s being willing to defer or delegate to anyone else. City lawyers suffer from the worst case of FOMO (fear of missing out), we know of – and they were doing so decades before FOMO became a thing. We have been to meetings that included lawyers expert in administrative law, litigation, zoning and planning, the building code, the Board of Standards and Appeals, economic development and the fire code – from both agencies and the Law Department – at one meeting. Not only is this wasteful, but it is also counterproductive. 

            In our legal career we have never been in an environment where attorneys are so disrespectful of the expertise and experience of others. Position and seniority are provided deference, but not subject matter knowledge. We have been in large meetings at which we have been the only attorney with expertise in an area of commercial law (having actually had extensive experience in commercial transactions outside of government), where all in attendance, regardless of subject matter knowledge, have voiced their opinions – and all opinions have been equally regarded by senior decision makers. Often, the loudest voice, the biggest bully, carries the day. A kind of radical equalitarianism prevails. If you scraped by at “Solomon” Law School or clerked at the Supreme Court, your opinion carries equal weight. If you have dealt with the subject matter for decades, or you just graduated from law school – all get to have their say. Again, no matter who has what level of expertise and experience, the Law Department representative has the last word.

There is a lovely bit of idealistic equality here – but it doesn’t result in thoughtful legal decision making. In addition, City government is filled with graduates of law schools that are, shall we say, not that of Kings College, and who simply aren’t very skilled or very smart. That’s a harsh judgement, but we are the former Chief Justice of the Supreme Court of the United States, and we were privileged to study at Kings and read law with Benjamin Kissam – so we are, admittedly, a legal and educational snob. Notwithstanding our former high position, we have never in our career had our informed judgement so routinely ignored – and prior to City government we worked with and for some significant reprobates. 

            All decisions are group decisions. No one person has responsibility for legal decision- making on any issue. This is probably in order to prevent responsibility from affixing to any particular lawyer for a decision. Judgments both major and minor are the results of meetings to discuss the issue;  and there are often multiple meetings on any particular issue. This also does not result in quality thinking. It enables the last and loudest voice from the Law Department to carry the day. It protracts the process. We have been involved in City contract negotiations over a $500 million matter that went on for two years after a default. We were, at least on paper, the person most responsible for the subject matter – and yet we were only tangentially involved in the negotiations – which were conducted by agency General Counsel and the Counsel to the agency’s Commissioner (yes, the agency had both), supported by an agency attorney with subject matter expertise as well as litigation counsel from the Law Department. Yes, there was plenty of legal talent on the matter without need of my aid. After the deal had been cut, different Law Department attorneys with sovereignty of this particular bailiwick, and who admitted that they did not have the requisite financial expertise to understand the transaction, flyspecked the innumerable legal documents for months. The number of irrelevant issues raised by Law Department attorneys, and by other agency attorneys (without particular subject matter expertise) called in to add their wisdom, were both breathtaking and ridiculous. 

            Having practiced in the private sector and interacted with City government for decades, we came to learn that while the City builds layers upon layers of protective vehicles into its documents, accreted over decades of drafting and redrafting,  IT ALMOST NEVER EXERCICES ITS RIGHTS. When were first assigned to negotiate a contract with the City as a young lawyer, we engaged in trench warfare, negotiating line by line and word by word – as one would do in a multi-million dollar private sector transaction. After a couple of decades of experience, we learned that this was pointless. The goal in negotiating with City government is to get the contract signed and approved; and to GET THE CHECK. If the deal were to go south, you should be fully aware that the City is unlikely to assert its contractual rights. The City often demands substantial security in the form of letters of credit and performance bonds in its agreements, and its negotiating posture appears to revolve around the minimization of risk. But we have never heard of the City actually drawing on contract security. And facts on the ground are dispositive. Once a private party is in the system to get paid, has title to real estate or has its equipment in place, the City rarely reverses course. Once you are in, you are in for good – regardless of how badly behaved a counterparty you are. Smart businesspeople and attorneys with experience with New York City government are well aware of this (It’s also amazing, though, how many sophisticated people aren’t!).

            City attorneys spend an inordinate amount of time congratulating themselves on how excellent they are, how avaricious and incompetent private sector lawyers are, and how successful City lawyers have been in getting their way. First off, they are generally incorrect. Secondly, they often think this because they have been outsmarted. Third, the City does often get its way because of its enormous bargaining power (it is has a $100 billion annual operating budget and over three hundred thousand employees), not because of brilliant negotiating. And last, and most importantly, it doesn’t matter because the City doesn’t enforce the provisions of its agreements anyway, and when it attempts to do so in court it generally loses. 

            The most obnoxious practice in the Law Department is putting notes and questions in the margins of documents sent to them for review. Law Department attorneys put in the margin whatever comes to mind; important, unimportant, irrelevant, the result of gastro-intestinal distress, it all goes in there. Law Department attorneys never redraft or suggest language. They just comment. So, agency attorneys and professional managers have to guess at what their Law Department colleagues are looking for. You redraft, and they tell you in a marginal note, “No, that’s not exactly right,” and send it back to you for another round. This can go on for months. There is one widely revered very senior attorney at the Corporation Counsel, with decades of Law Department tenure, who has the last word on a wide range of financial transaction documents who i) never provides drafting, ii) can offer as few as one comment in a round of review, iii) can continue to provide comments for endless rounds and iv) has no sense of time or priorities. Stuff sits on his desk for months. But he is respected for his ability to find problems with documents. It is not his, or his colleagues, job to solve problems. They find problems; they issue spot like on law school exams.  When we were trained as an attorney, we learned that it is a lawyer’s job to solve problems. It is not clear to us whose interests the New York City Law Department is representing in pointing out, rather than solving, legal issues. Most of the issues they raise are so arcane as to not possibly protect any material interests of the City of New York. It’s a kind of academic exercise with the impact of bogging projects down for months and years. This has become a serious impediment to creative problem solving and new initiatives in City government. No one in authority puts a stop to this. Few City attorneys feels responsible for getting matters to closure. 

There might be some virtue in this course of dealing if the City’s contracts were so iron-clad that the City had a fearsome reputation for winning motions to dismiss in lawsuits (a motion that stops a lawsuit from proceeding shortly after a complaint commencing an action has been filed) – but the opposite is true. The City regularly gets bogged down in Jardyce v Jardyce like conflicts (except dealing with major economic and policy issues) that spend years in court without resolution. We were involved with the settlement of a six-year-old case filed by the City that was celebrated by colleagues and by press releases as a major win for City government, but, in our experienced estimation, was the best possible result for the interests of the City’s adversary in the litigation. They got exactly the result they were looking for when they breached their contract with the City years before.