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Opposition War-Gaming

When to use

You've drafted (or are about to draft) a brief or motion, and you want to stress-test it by imagining the best possible opposition. Also useful before oral argument to prepare for tough questions, or when advising a client on litigation risk before filing.

Prompt

You are opposing counsel. Your job is to write the strongest possible response
to the brief or arguments I describe below. You are smart, thorough, and
relentless — but not dishonest. You will not misstate authority or invent
facts.

Produce your war-gaming analysis in these sections:

## 1. Theme
If you were opposing counsel, what is your one-sentence counter-narrative?
The frame that makes the judge see the case your way from the start.

## 2. Argument-by-Argument Response
For each argument in our brief:
- **Our argument** (restate in one sentence).
- **Best response** — the strongest counterargument, fully developed. Include:
  * The legal rule or authority that supports the opposing position.
  * How opposing counsel would distinguish our best cases.
  * How opposing counsel would use the facts (or the complaint's allegations)
    to support their reading.
  * Any procedural or standard-of-review arguments that help the opposing
    side (e.g., "at the motion to dismiss stage, all inferences favor
    plaintiff").
- **Strength assessment** — rate the counterargument: Strong (we should worry
  about this), Moderate (arguable but we have the better side), or Weak (we
  can handle this easily). Explain the rating in one sentence.

## 3. Arguments We're Not Making (but should be worried about)
Identify any arguments the opposing side might raise that our brief doesn't
address at all. For each:
- State the argument.
- Assess whether it has merit.
- Recommend whether we should preemptively address it or wait for the
  opposition to raise it (and why).

## 4. Factual Vulnerabilities
Identify any facts in the record (or allegations in the complaint) that we
are glossing over, under-emphasizing, or hoping the court won't notice. For
each:
- The fact or allegation.
- How opposing counsel would use it.
- How we should handle it (address head-on, distinguish, or argue
  immateriality).

## 5. Questions from the Bench
Draft the five hardest questions a skeptical judge might ask us at oral
argument, based on the weak points you've identified. For each question,
draft a proposed answer.

## 6. Overall Vulnerability Assessment
On a scale of 1-10 (10 = bulletproof, 1 = we should settle), rate our
position's overall strength. Explain the rating in a short paragraph
identifying the single biggest risk.

Constraints:
- Argue the opposing position forcefully. Do not pull punches, add caveats
  about why we might still win, or reassure me. I want to see our case at
  its weakest.
- [VERIFY] any case you cite for the opposing side. If you are not confident
  an authority exists or stands for the proposition, flag it.
- Do not make arguments that rely on facts outside the record or allegations
  outside the complaint. Opposing counsel is smart but honest.
- If our position really is strong on a particular argument, say so — don't
  manufacture weaknesses that aren't there.

Our brief / arguments:
{{paste brief text, argument outline, or summary of the position you want
stress-tested}}

Procedural posture:
{{motion to dismiss / summary judgment / trial / appeal — affects what
inferences the court draws and what evidence is in play}}

Key facts / record:
{{paste any factual background or record materials the opposing side would
have access to}}

Notes / variations

  • For a full mock opposition brief, replace the structured analysis with: "Draft the opposition brief itself — Introduction, Statement of Facts (from their perspective), Argument, and Conclusion — as though you are filing it. Use the same page limit as our brief."
  • For appellate oral argument prep, focus on section 5 and expand to 10-15 questions, organized by argument section, with both "hot bench" questions (hostile) and "cold bench" questions (seeking genuine clarification).
  • For pre-filing assessment (before you've drafted anything), simplify: provide just the claim or defense theory and ask for sections 2, 3, and 6 to assess viability before investing drafting time.
  • Pair with the Brief Redline prompt after this exercise to revise the draft in light of the vulnerabilities identified.