Almost every significant case has one.
The fact you wish weren’t there.
The email you wish your client hadn’t sent. The deposition answer you wish the witness hadn’t given. The document with the unfortunate language. The chronology that doesn’t quite work. The prior statement that seems inconsistent. The conduct that is difficult to explain.
You know the fact is there. Opposing counsel certainly knows it’s there.
And yet there is an enormous temptation to treat it like the monster outside the door: if we can just keep pushing hard enough, maybe it won’t get into the case.
It usually doesn’t work.
The monster is already there.
The strategic question isn’t how to make the bad fact disappear. It is what you’re going to do with it.
First, Find the Facts That Frighten You
When I work with lawyers on a case, one of the questions I like to ask is deceptively simple:
What is the fact in this case that you wish would just go away?
The answer can be enormously revealing.
Trial lawyers naturally spend a great deal of time identifying the evidence that helps them. We build chronologies. We identify admissions. We find documents that support our theory. We prepare the witnesses who can tell our story.
But case strategy also requires an uncomfortable exercise: identifying the facts that threaten the story.
And that exercise should happen early.
Don’t ask only:
What are our best facts?
Ask:
What will opposing counsel say is our worst fact?
And then ask something even harder:
Are they right?
Sometimes lawyers become so accustomed to the facts of their own case that they stop experiencing them the way a judge or jury will experience them for the first time.
A fact we’ve spent six months explaining to ourselves may look devastating to someone who hears it in six seconds.
That is why the first task isn’t explaining the bad fact.
It is recognizing it.
How Bad Is the Bad Fact?
Not every uncomfortable fact is fatal.
Some facts look terrible until they’re placed in context. Some require an explanation. Some expose a weakness but don’t undermine the central theory of the case. And occasionally the fact everyone has been worrying about turns out not to matter very much at all.
But you can’t know which kind of fact you have until you stop defending it long enough to examine it.
I like to ask:
What conclusion will the other side ask the jury to draw from this fact?
Then:
Is that a reasonable conclusion?
If it is, we have work to do.
The goal isn’t to invent a clever explanation. It’s to understand the fact well enough to decide whether it can be contextualized, distinguished, conceded, or incorporated into the larger theory of the case.
Sometimes the best response to a bad fact is a strong explanation.
Sometimes it is a short explanation.
And sometimes the most credible response is:
Yes. That happened.
Then explain why it doesn’t answer the question the jury is actually being asked to decide.
Sometimes the Answer Isn’t a Better Explanation. It’s Better Context.
I once represented a woman in an employment case who was warm, funny and genuinely likable. She got along well with her coworkers, and that was entirely consistent with the person I came to know.
Then I found an email.
In the middle of a series of exchanges with the supervisor who ultimately fired her, my client suddenly began writing in ALL CAPITAL LETTERS. Some of the language was also bolded and underlined.
In today’s parlance, she was shouting.
Standing alone, the email worried me.
It portrayed a very different person from the woman a jury would meet in the courtroom. I could easily imagine opposing counsel putting the email on a screen and suggesting that the pleasant, reasonable woman sitting before the jury wasn’t quite so pleasant or reasonable when she was dealing with her supervisor.
But then I read the entire email chain.
My client had asked her supervisor a question.
The supervisor didn’t answer it.
She asked again.
No answer.
Again.
No answer.
This happened seven or eight times while my client was becoming increasingly ill in the workplace.
Eventually, she had had enough.
And then came the capital letters.
The email hadn’t changed.
But its meaning had.
Viewed in isolation, it looked hostile. Experienced in sequence, it looked like the culmination of mounting frustration after repeated attempts to get help were ignored.
And that presented a strategic opportunity.
I didn’t need to stand in front of the jury and say:
Please don’t hold this email against my client. Let me explain why she wrote it.
Instead, I could let the jury experience the same sequence she experienced.
Question.
No answer.
Question again.
Still no answer.
Again.
Again.
And only then:
the all-caps email.
By the time the jury encountered the supposed “bad fact,” they already understood how we got there.
That’s an important distinction.
Sometimes the answer to a bad fact isn’t a better explanation.
It’s better context.
DON’T LET YOUR OPPONENT DEFINE THE BAD FACT
There is another strategic decision that matters enormously:
Who should tell the jury about the bad fact first?
Imagine that you’ve spent the first two days of trial presenting your client in the most favorable possible light.
Then opposing counsel stands up on cross-examination and produces the document you’ve carefully avoided mentioning.
Suddenly the problem isn’t merely the document.
The jury may begin wondering:
Why didn’t they tell us about this?
You’ve potentially transformed a difficult fact into a credibility problem.
Sometimes the strongest way to deal with damaging evidence is to put it on the table yourself.
Not apologetically.
Not defensively.
And not with a 20-minute explanation that announces to everyone in the courtroom how terrified you are of it.
Just deal with it.
You may decide to acknowledge it in opening. You may bring it out through your own witness. You may place it in context before opposing counsel has an opportunity to characterize it.
The right choice depends on the case.
But it should be a choice—not something that happens because you spent the entire trial hoping opposing counsel wouldn’t open the door.
Taking the Sting Out Is Only Part of the Strategy
Lawyers often describe this as “taking the sting out” of a bad fact.
That’s useful, but I think the strategic opportunity can be larger.
The way you deal with a weakness can become evidence of your credibility.
If you acknowledge something the jury knows hurts you, you’re demonstrating that you’re willing to talk about the entire case—not simply the portions that help you.
That can matter later.
When you tell jurors:
This fact matters.
And later:
This other fact doesn’t mean what opposing counsel says it means.
You want them to trust that you’re making those distinctions honestly.
Credibility is accumulated.
Sometimes a bad fact gives you an opportunity to earn some.
Can the Bad Fact Actually Help You?
Occasionally, something even more interesting happens.
The fact you originally wanted to hide becomes useful.
Perhaps it allows you to explain why your client did something that otherwise seemed inexplicable.
Perhaps it demonstrates that your witness isn’t exaggerating.
Perhaps acknowledging your client’s mistake makes the larger accusation against your client less plausible.
Or perhaps the fact fits a broader proposition:
Real life is messy.
People don’t behave perfectly. Businesses don’t create perfect records. Memories aren’t perfect. Good people make poor decisions. A witness can be wrong about one thing without being dishonest about everything.
A case that requires the jury to believe your client has never made a mistake is often a fragile case.
Sometimes conceding the mistake makes the rest of the story considerably more believable.
Ask the Question Before the Jury Does
There is a broader lesson here.
Good trial preparation isn’t simply the process of accumulating favorable evidence.
It is the process of looking at your case from outside your own theory of it.
What makes you uncomfortable?
What requires too much explanation?
What fact causes everyone on the trial team to change the subject?
What will opposing counsel put on the screen in closing?
What will the jurors talk about when they are finally alone in the deliberation room?
Those are not questions to save for the eve of trial.
Ask them while there is still time to do something about the answers.
Because the fact you wish would just go away probably isn’t going anywhere.
The monster is already on the other side of the door.
Your job isn’t to pretend it isn’t there.
Your job is to decide what the jury is going to think about it when the door finally opens.

