Hard cases make bad law
- 2 hours ago
- 7 min read
You have invested months and substantial legal fees in a serious commercial matter. Your legal team has gathered the evidence carefully. The case logic is sound. The hearing is professional. Your lawyers perform well. When judgment arrives, the outcome often turns on factors you never thought would influence the judge. The work you did not see carries the day, or ruins the case.
This is the fifth and final article in Wessel’s rules of practice series. The rule it examines is the one most often confused with elegant drafting. Elegance is visible on the page. The discipline that decides the outcome is not.
Hard cases make bad law
The case is often won before argument starts
Most commercial lawyers have experienced a crowded commercial motion court on the morning of argument. Senior counsel for the applicant takes the seat closest to the bench, a junior beside him and another behind. Across the bar, senior counsel for the respondent and his juniors. Behind them, two instructing attorneys and the associates carrying the bundles. Four lever arch files on each side. The heads of argument in its own file on top of each pile. An army of lawyers, facing a single judge.
Argument proceeds. Senior counsel for the applicant takes the judge through the founding affidavit. She critically tests him against the answering affidavit with the questions she has prepared. He answers what he can answer. He concedes what he must concede. Where the answer needs the documents, he sends her to them. The respondent has his turn. By the end of the afternoon, both sides have finished. The judge thanks counsel, indicates that judgment is reserved, and rises.
The court adjourns. The room empties within minutes. Senior counsel returns to chambers where three other matters are waiting. The juniors go back to the work they were running before this one. The attorneys go back to their offices, where the next set of papers is already overdue. The associates carry the bundles out. The client goes back to his business. The judge is left alone in her chambers with the file.
Most people think what they have just read is what law is. The gowns. The senior counsel in silk. The lever arch files four high on each side. The judge testing the advocate with questions she has prepared, the advocate answering them on his feet in the language of the courts. The theatre is real and it is serious. The gravity of the courtroom is what allows the parties to commit their dispute to the legal process and to accept the conclusion that comes out of it. It is not pageantry. It is the architecture of trust.
But the courtroom is not where the matter is decided.
What the cliché missed
There is an old truism of the English common law, repeated for at least two centuries by judges in many jurisdictions including our own. Oliver Wendell Holmes Jr. used it in dissent in 1904, in Northern Securities Co. v. United States. Holmes wrote that great cases, like hard cases, make bad law.
The traditional reading of the cliché is straightforward. Hard facts pressure the law to bend, and the bent law sits as precedent for the cases that follow.
There is another version of the saying, less often spoken aloud but more often true. The cases that make bad law are not always hard because of their facts. They are sometimes hard because the lawyers who put the case in front of the judge made it hard. A matter that should have been straightforward arrives in chambers in disarray. The judgment she writes from a poorly placed file is rarely the best judgment the case allowed. The next court that reads it inherits the law she had to write.
Where is the decision actually made?
The matter is decided in the judge’s chambers, alone with the file. The judgment will be written in the time the judge can find, and the time is not generous. There are reserved judgments from earlier in the term still on her desk. Two opposed motions from this week need writing. A trial starts on Monday. The unopposed divorce roll is on Friday. The judge is under pressure from inside the system. Reserved judgments are tracked. The senior judge in her division will know how long this judgment has been outstanding. The litigants are entitled to it within a reasonable time. She will write in her evenings, on Saturdays, and on Sundays between everything else.
She must decide the case from what is in the file, under pressure, constrained by what the parties have properly placed before her. She must produce a judgment that will withstand scrutiny from losing counsel, because the system depends on her to deliver. The lawyers who lost will read her judgment looking for the line that gives them an appeal point.
Her judgment remains a permanent record, produced from the file in front of her. Every paragraph in it was arranged by the lawyer who drafted it. Every annexure was sequenced. Every heading was chosen and placed.
What turns the dial?
There is a temptation to think that what wins a commercial matter is the basics. Coherent papers. A clear chronology. A founding affidavit that lays out the facts in the order they need to be understood. An answering affidavit that engages the founding paragraph by paragraph. Heads of argument that distil the dispute into the questions the court must answer. Senior counsel who can hold the line under pressure from the bench. These are the basics. But they are not what actually turns the dial.
The X-factor is the thousand small decisions the lawyer made before the matter ever reached the courtroom. Most were invisible at the time they were made. Most remain invisible after the judgment is delivered. They are decisions about where each fact should sit: which paragraph should carry which point, which annexure should attach to which proposition, what belongs in founding, what should be held for reply, what belongs in the affidavit, what belongs in the heads, and what should be left out altogether because including it would distract the judge from the path the law and the facts permit.
What does placement look like?
I learned placement in the trenches. The papers we draft in serious matters are written for results, not for show. They have to be elegant, coherent, of a high literary standard. But the elegance is not the purpose. The purpose is to persuade the judge in the hours when the file has to do its work without us. That is the north star around which every placement decision is made. Does this advance the case, or does it detract from it?
The work begins long before the founding affidavit is drafted. It begins in the first consultations with the client. I have learned to listen with two ears at once. With one I hear the client’s story as the client tells it. With the other I hear what the judge in chambers will eventually have to decide. The two stories are rarely the same. The client’s story has decades of context, grievances, vindications, and emotion in it. The judge’s story will have only what the file makes available, in the order it makes it available, and only what advances the case I have chosen to make.
Many of the matters that have reached me over the years have not arrived clean. They come after earlier litigation, failed negotiations, years of correspondence, parallel processes, and accumulated grievance. The client brings a long history, but the court does not need the whole history. It needs the part that allows it to decide the case properly. Placement is critical in that conversion. The lawyer must take a sprawling dispute history and distil it into a case the court can decide. That means selecting what belongs in the founding affidavit, what must wait for reply, what carries in the heads of argument, what must be annexed, where each annexure sits, and what must be left out. In those matters, the difference often lies less in discovering a new point than in putting the existing facts into a shape the court can use.
The conversation that follows the first draft is one of the harder conversations in this profession. The client wants everything in. He has memorised every detail of his side. He cannot understand why the lawyer who is on his side is leaving things out. I have had this conversation more times than I can count. The point the client wants in the founding is, more often than not, a point that will weaken his case in front of the judge on the issue she will have to decide. Some of it belongs in reply, where it can answer the other side rather than anticipate them. Some belongs in the heads of argument, where it can frame the law rather than carry the burden of being sworn. Some belongs nowhere in the papers.
The hardest placement decision in legal advocacy is the decision not to say something. Many lawyers cannot make it. They cannot face the client who wants the point in. Their papers carry every point the client wanted, and the case is weaker for every one. I have lost the same conversation with the same kind of client more times than I have won it. Sometimes I prevail and the point stays out. Sometimes the point goes in and the client is happier and the case is weaker.
What the file allows
Bad placement makes bad law. The judge faced with a poorly placed file has to do the work the lawyer was paid to do. She has to reconcile a chronology in the heads against a narrative in the affidavits that does not support it. She has to draw the inference the cross-reference was supposed to draw for her.
A judge may not find a material letter, resolution, notice, or board minute because it has been attached as one item in a long series of correspondence, somewhere near the back of the founding affidavit, out of chronology and without a cross-reference that explains why it matters. If that document is missed, or found too late, the judgment may move in a different direction. Once that happens, other facts are read through the wrong line of reasoning or become irrelevant to the issue the judge thinks she has to decide. The case becomes skewed, not because the fact did not exist, but because it was not properly placed.
The file is the only thing the judge has when she sits down to write. Argument is over. The advocate is gone. What was placed in the file is the case; what was not placed there does not exist for the purposes of the judgment.
The hard cases that make bad law are sometimes hard because the facts are hard. They are more often hard because no one placed them. Good placement is not tidying the file. It is deciding what matters, where it belongs, and what must be left out so the judge can see the case clearly.
Good papers are drafted. Great papers are placed.
Written by:
Wessel Badenhorst
June 2026
