Start with What Scares You Most
Most attorneys build their case from the inside out. They identify their strongest points, marshal their best evidence, and present their argument in the most favorable light. Then they wait to see what the opposition throws at them.
This approach feels natural. It plays to our strengths and lets us showcase what we do best. But it leaves a critical gap: you enter the courtroom reactive instead of prepared.
A counterargument-first method flips this script. Before you finalize any significant motion or appellate brief, you script the best argument the other side could make. Not a weak version or a straw man, but the most compelling, fact-based position your opponent could present. Then you structure your entire case to preempt it.
This is not about pessimism. It is about preparation that wins.
Why the Standard Approach Falls Short
Traditional case preparation focuses on affirmative arguments. You outline your theory, cite your precedents, and build a narrative that supports your client’s position. When opposing counsel raises a point you did not anticipate, you scramble to respond in real time.
The problem is twofold. First, judges notice when an argument feels reactive. A hurried response signals that you were caught off guard, which undermines your credibility. Second, you lose the chance to frame the counterargument on your terms. Once the other side introduces a point, they control how it enters the record.
Jerome Murphy, a partner with Tressler LLP in Chicago who handles complex litigation and appellate matters, learned this lesson early in his practice. After receiving an unfavorable ruling on a significant motion, jerome murphy palos heights realized he had built his arguments around his client’s strongest position instead of anticipating the opposition’s best case. “I changed how I prepared for any significant argument, either in trial or appellate court,” he explains. “I now script the best counterargument the other side could make and make sure my position preempts that argument, rather than just presenting my own case.”
The shift produced measurably better outcomes. More importantly, it changed the dynamic in the courtroom.
How to Script the Opposition’s Best Case
Begin by setting aside your own brief. Imagine you represent the other side. What facts hurt your current client most? Which legal precedents create the tightest bind? Where does the record give the opposition room to argue?
Write it out in full paragraphs, not bullet points. Use the same level of detail you would for your own brief. Cite actual cases. Quote from the record. Construct the argument as if you were filing it tomorrow.
This exercise is uncomfortable. You will feel like you are sabotaging your own case. That discomfort is the point. If a counterargument makes you uneasy when you write it in private, it will do worse damage when opposing counsel presents it in open court.
Once the counterargument is on paper, identify its weight-bearing walls. What facts does it depend on? What inferences must a judge accept for it to hold? What legal standard does it require?
Then dismantle those supports in your affirmative case. Do it early, before the opposition has a chance to frame the issue. If your counterargument depends on a particular reading of a statute, address that interpretation in your opening section and show why it fails. If it relies on a specific fact pattern, distinguish it clearly before anyone can draw the parallel.
Preemption vs. Rebuttal
Preemption and rebuttal sound similar, but they function differently. A rebuttal responds to an argument after it has been made. Preemption addresses it first, in a way that makes the opposing argument feel redundant or already answered.
When you preempt, you control the framing. You get to explain why a particular case does not apply, or why a fact pattern is distinguishable, before the other side has painted it as decisive. Judges read your explanation first, and that sequence matters. The brain anchors on the first coherent narrative it encounters.
Rebuttal, by contrast, forces you to dislodge an idea that has already taken root. Even if your response is strong, you are now playing defense. The judge has already considered the opposing view, and your job is to convince them they were wrong to find it persuasive.
Preemption is proactive. Rebuttal is damage control.
Where This Method Pays Off Most
This approach delivers the highest return in three settings: dispositive motions, appellate briefs, and oral arguments.
Dispositive motions—summary judgment, motions to dismiss, motions for directed verdict—hinge on legal standards and undisputed facts. Judges decide them on the briefs, often with minimal oral argument. If the opposing brief introduces a case or factual distinction you failed to address, you may not get a second chance to respond. Preempting those arguments in your opening brief keeps you in control.
Appellate briefs face even tighter constraints. Appellate judges review cold records and rely heavily on written submissions. If your brief ignores the strongest counterargument, the appellate panel will notice. Worse, they may adopt the other side’s framing because you gave them no alternative.
Oral arguments compress everything into minutes. You cannot afford to spend half your time responding to points you should have anticipated. If you have preempted the key counterarguments in your brief, oral argument becomes an opportunity to reinforce your strongest points rather than a scramble to plug gaps.
Common Pitfalls and How to Avoid Them
The biggest mistake is scripting a weak counterargument. If you only address the opposition’s second-best case, you waste the exercise. Steelman the argument. Make it as strong as you can. If that version still collapses under scrutiny, you know your position is sound. If it does not, you have identified a genuine vulnerability that needs more than a cursory response.
Another pitfall is over-explaining. Once you have preempted an argument, move on. Lingering too long signals anxiety and invites the judge to question whether the issue is as settled as you claim. Address it clearly, dismantle it efficiently, and return to your affirmative case.
Finally, do not let preemption turn into a defensive brief. Your primary goal remains persuading the court of your client’s position. Preemption is a tool to remove obstacles, not the centerpiece of your argument. Structure your brief so the affirmative case carries the narrative, with preemptive sections woven in where they do the most work.
Building the Habit
This method requires more time up front. Scripting the opposition’s case, analyzing its weak points, and restructuring your brief to preempt key arguments adds hours to your preparation. But it saves time later. You spend less effort responding to opposition briefs, less time revising your arguments after an unfavorable hearing, and less energy second-guessing your strategy.
Make it routine. For every significant motion or brief, set aside an afternoon to write the counterargument in full. Treat it like a draft you will never file but must complete. Over time, the exercise becomes faster as you train yourself to spot vulnerabilities earlier in the process.
The payoff is not just better results. It is confidence. Walking into a courtroom knowing you have already addressed the hardest question the judge could ask changes how you present. You sound less like an advocate hoping for the best and more like a lawyer who has already thought three steps ahead.
That difference is what judges remember.
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