Why Can’t They Say “Yes” or “No”? Understanding How Lawyers Talk to Business People (Part 3 of 4)

This series is about how the legal system’s subjective and arbitrary character constrains your lawyer from answering “yes” or “no”.
Sometimes a judge’s personal idiosyncrasies distinctive, well-informed judgments may drive the outcome more than an objective view of the law or evidence.


My own introduction to this came when I was a prosecutor in Manhattan. When my colleagues and I brought a felony case we — collectively — knew all of the personalities among the judges on the trial court to whom that case might be assigned.

And our prosecutors’ grapevine functioned well. We each had either firsthand experience — or readily available, reliable accounts of a professional colleague — to inform the way we argued law or handled evidence before any particular judge.

Some judges tended to disbelieve police testimony. Others would never impose a greater sentence than the law absolutely required. Some were meticulous on evidentiary objections. Others were relatively loose on such rulings. Some were temperamental. Others were reasonable.

Learning the judge’s personal idiosyncrasies was always my first order of business when I was assigned to a particular judge for trial.

In the last few years lawyers and (computer) code-writers have begun to create — via software — what my prosecutor colleagues and I had by word-of-mouth.

Example: “‘Moneyball’ Legal Analytics Helps Lawyers Assess Judges“:

“Intellectual property lawyer Huong Nguyen walked into a federal courtroom a few years ago to defend a case for a maker of generic pharmaceuticals. Another lawyer told her that the judge had a reputation of favoring name-brand drug makers, which would normally suggest that Nguyen might lose at the trial level. But one source of information made her believe that she had a better shot: legal analytics.

Using software made by Menlo Park startup Lex Machina, Nguyen was able to see how the judge had ruled in previous cases that matched details of hers. She found that he had once ruled in favor of a generic maker, like the one she was representing. The parties ended up settling, she said — far better than losing.”

Add to Lex Machina names like Ravel Law, Bloomberg Law Litigation Analysis, Westlaw Profiler — and a handful of others.

Finally, one more way that the “human factor” affects how judges’ distinctive traits can drive your case’s outcome:

Trial courts of general jurisdiction or appellate courts of general jurisdiction are just that: They’re “general”. In this general jurisdiction context a judge’s strengths — or weaknesses — can have a big effect on how your case is tried or settled.

A positive example: Before he retired from the U.S. District Court for the Northern District of Illinois, former Chief Judge James Holderman was known for his expertise in intellectual property cases.

If you had a complicated patent case in Chicago’s federal trial court you prayed for an assignment to Judge Holderman’s docket.

A negative example: A few years ago I found myself in front of an Illinois Circuit Court judge in a downstate city. I was collecting on a judgment for money damages before a judge who’d been on the bench all of two months.

On hearing my request — and reading my motion which asked for access to the debtor company’s financial records — the judge scolded me:

“Mr. Webber, this is a collection proceeding — not pretrial discovery where you can ask for those sorts of things.”

I replied:

“With respect, Your Honor, Section 1402 [the applicable collection statute in Illinois law] gives me robust rights to books and records in this situation.”

The judge didn’t reply. She immediately declared a recess, and left the bench for 15 minutes.

During which — it’s my educated guess — she read the collection statute I’d cited.

Anyway, when she returned she granted my request in its entirety.

What was that all about?

Before having assumed the bench, this judge — like many successful lawyers — had concentrated her practice in one area of the law. In fact, she’d enjoyed a national reputation in that one area.

But her national reputation was in criminal law — not commercial law.

And upon entering a court of general jurisdiction she faced a learning curve — and as a practicing lawyer I needed to address that gap in her inexperience.

[Reposting of a previous post from October 24, 2018]

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