Why Some “Good Cases” Still Don’t Settle

Every lawyer has seen it: a strong case, good facts, capable counsel, and enough money on the table to resolve it. And yet—it doesn’t settle.

When cases like this fail to resolve, it’s rarely because the law is unclear. More often, it’s

because human decision-making is far less rational than we’d like to believe.

Here are the most common reasons good cases still don’t settle:

1. The Case Has Become About Identity, Not Risk

Over time, cases stop being about exposure and start being about being right. Lawyers and clients alike can become emotionally invested in the narrative. When that happens, settlement begins to feel like surrender—even when it’s objectively the best business decision.

2. Fear of Regret Outweighs Fear of Loss

Many parties don’t evaluate settlement based on expected value. They evaluate it based on what they’ll feel if they’re wrong.

• “What if we settle and the jury would have given us more?”

• “What if we pay this and could have won?”

This fear of future regret often freezes decision-making more effectively than any legal argument.

3. Anchoring Has Quietly Taken Over

The first serious number in a case—whether a demand, a reserve, or an early valuation—often becomes psychological gravity. Even when new information emerges, parties stay tethered to old numbers long past their usefulness.

4. The Process Rewards Fighting, Not Resolving

Litigation trains people to:

• Defend

• Attack

• Win motions

• Prove points

  
  

It does not train people to make good resolution decisions under uncertainty.

By the time mediation arrives, many parties are excellent litigators—but poor risk managers.

5. The Last 10% Is Emotionally Harder Than the First 90%

Most deals fail near the finish line.Why? Because the final concessions feel personal, not mathematical. The closer you get, the more each move feels like a loss instead of a solution.

The Mediator’s Real Job

A mediator’s job isn’t just to move numbers.It’s to help people make decisions in the presence of fear, pride, fatigue, and uncertainty.

Good cases don’t settle because they’re good.They settle because the decision-makers are ready to decide.

Final Thought

If a “good case” isn’t settling, the obstacle is rarely legal.

It’s human.