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Grammar in Real Cases

Passives, apostrophes, and commas

Legal writers should always aim for grammatically correct prose. Why? To me, the key reason is to establish and maintain credibility: When readers see that you know how to write correctly, they are also likely to believe that you stated the facts and law correctly and presented accurate, valid arguments, explanations, or advice.

But occasionally, grammar itself becomes an issue in a case. Here are some grammatical matters that made it into caselaw, including one that made headlines. For the first three examples below, I thank Professor Diana Simon and her excellent book, The (Not Too Serious) Grammar, Punctuation, and Style Guide to Legal Writing published by Carolina Academic Press in 2022.

Although using the passive voice is not a grammar error, using it unwisely can have bad consequences. In one case, a due-process claim written in the passive voice failed to identify who did the “assuring” in the following statement from the complaint: “she was assured that she would continue on the job as long as she performed satisfactorily.” As a result, the judge dismissed that claim.[1]

In another case, a lawyer used apostrophes inconsistently in a settlement offer before trial—sometimes Plaintiffs and sometimes Plaintiff’s. The court said, “The offer was apostrophe-challenged, creating ambiguities ….” Thus, the offer failed to satisfy the particularity requirement, and the court reversed an award of attorney’s fees.[2]

One case involved a comma splice—joining independent clauses with only a comma when a period, semicolon, or conjunction is called for. A federal district judge, attempting to apply state law, noted, “The Supreme Court of South Dakota first recognized a cause of action for insurance bad faith in [Champion]. The published version of the Champion case unfortunately … employed a comma splice in a key passage, creating a confusing standard.”[3]

And then there’s a serial-comma case that made some headlines in 2018.[4] Under Maine law, overtime-wage laws do not apply to—

The canning, processing, preserving, freezing, drying, marketing, storing, packing for shipment or distribution of: [certain products].[5]

The question:

  • Is “packing for shipment” one activity, and “distribution” a separate activity?

That would be correct if there had been a serial comma after “shipment.”

  • Or is the activity, “packing for shipment or distribution”?

That would be correct if the drafter was a practitioner of the serial comma but had intentionally omitted it because “packing for shipment or distribution” was intended to be a single activity.

The specific question before the First Circuit was about truck drivers: if distribution is a separate activity, drivers are not entitled to overtime pay. But if the activity is “packing for shipment or distribution,” the drivers are entitled to overtime pay because drivers don’t pack; they distribute.

The court declined to apply Maine’s Legislative Drafting Manual, which calls for omitting the serial comma—a common approach, especially in journalism. That would have made “packing for shipment” a separate activity from “distribution,”  and the drivers would not be entitled to overtime pay.

Instead, the court relied on parallelism, pointing out that the listed activities were all gerunds (-ing) except for distribution, and as a result, distribution was not a separate activity, but a part of the “packing” activity.

Treating “packing for shipment or distribution” as a single activity means that the list lacked a conjunction. Thus, the “or” in “packing for shipment or distribution” was part of that single activity and could not serve as the conjunction for the larger list.

Can you have a list without a conjunction before the last item, even if you don’t use a comma?

Yes, you can, although doing so is a rhetorical technique called “asyndeton.” Asyndeton means creating a list but omitting the coordinating conjunction: The flag is red, white, blue (omitting “and”). So although the court expressed some distaste for the idea, it implicitly accepted asyndeton as a legitimate drafting practice.[6]


[1] Ponder v. Cnty. of Winnebago, 2021 WL 3269842, *7, *12 (N.D. Ill. Sept. 30, 2021).

[2] Bradshaw v. Boynton-JCP Assocs., 125 So. 2d 289, 289, 290 (Fla. Dist. Ct. App. 2013).

[3] Anderson v. W. Nat. Mut. Ins. Co., 857 F. Supp. 2d 896, 903 (D.S.D. 2012).

[4] An Expensive Dispute About Serial Commas, ABA Journal (May-June 2018)​real_property_trust_estate/publications/probate-property-magazine/2018/may-june-2018/an-expensive-dispute-about-serial-commas/

[5] Me. Stat. tit. 26 § 664(3)(F).

[6] O’Connor v. Oakhurst Dairy, 851 F.3d 69, 71, 73, 76, 80-81 (1st Cir. 2017).

Clearly, you should really avoid adverbs

The best-selling author Stephen King hates adverbs and advises writers not to use them:

The adverb is not your friend. Adverbs … are words that modify verbs, adjectives, or other adverbs. They’re the ones that usually end in -ly. With adverbs, the writer usually tells us he or she is afraid he/she isn’t expressing himself/herself clearly, that he or she is not getting the point or the picture across.

I believe the road to hell is paved with adverbs, and I will shout it from the rooftops. To put it another way, they’re like dandelions. If you have one on your lawn, it looks pretty and unique. If you fail to root it out, however, you find five the next day… fifty the day after that… and then, my brothers and sisters, your lawn is totally, completely, and profligately covered with dandelions. By then you see them for the weeds they really are, but by then it’s—GASP!!—too late.

Three points:

First, King writes fiction, and I focus on legal writing, but still, plenty of lawyers have quoted King on adverbs.

Second, all the highlighted words in those quotations are adverbs. (But maybe King was being facetious with the green words?)

And third, on just the first page of one of his short stories, King used 10 adverbs:

  1. finally
  2. ever
  3. across
  4. utterly
  5. listlessly
  6. slowly
  7. finally
  8. doubtfully
  9. flat (as in “it fell flat”)
  10. periodically

What should we make of this? That people exaggerate? That people often ignore their own advice? That people offer advice that applies to others but not to themselves? That advising against adverbs is common writing advice, so people spout it without really thinking?

Headings, part 2: Consistency, Outlining, and Numbering

Nearly every legal document can benefit from clear, consistent headings. Here in part 2, I offer recommendations for making headings consistent, commend some traditional outlining rules, and suggest a simple numbering system. These guidelines should help you create readable, skim-able documents.

Your headings should form an outline, and in outlines, entries at the same level should be structured and formatted the same way. That may seem obvious, but not all legal writers do it, as I recently learnedwhen reading motions and briefs in preparation for a CLE seminar.

For example, suppose an Argument has the following heading outline:



In that outline, 1 and 2 are at the same level, so they should be structured and formatted the same way. Likewise, both a and b pairs are at the same level, so all four should be structured and formatted the same way.

Specifically, if 1 is a topic heading in boldface initial caps, then 2 should be a topic heading in boldface initial caps. If 1a and 1b are full-sentence, explanatory headings in italics, then 2a and 2b should also be full-sentence explanatory headings in italics. For example—

1. Trial Court Errors
a. The trial court erroneously instructed that police officers may pretend to be electors.
b. The trial court failed to have the court reporter record statements made on audio recordings.

2. Sufficiency of the Evidence
a. Sufficiency of the evidence on attempted election bribery.
b. Sufficiency of the evidence on conspiracy to commit election fraud.

The structure of 1a and 1b (full sentences) does not match the structure of 2a and 2b (phrases). We need to revise 2a and 2b into full-sentence, explanatory headings. The format, italics, should match, too.

In creating headings and sub-headings, follow two key outlining rules.

Rule 1: Keep main topics at the same level and keep sub-topics at the same, lower level. So don’t place main headings and sub-headings at a single outline level. For example—

1. Preliminary Statement
2. Argument
3. The Plaintiff Cannot Prove Consequential Damages.
4. The Plaintiff Cannot Prove Expectation Damages.
5. Conclusion

1. Preliminary Statement
2. Argument
a. The plaintiff cannot prove consequential damages.
b. The plaintiff cannot prove expectation damages.
3. Conclusion

Rule 2: Don’t create a sub-heading unless you have two. If you have only one sub-heading, incorporate it into the main heading. But if your argument or discussion contains only one major issue, it’s okay to have a single major heading for that issue. For example—

a. The suit is barred by laches.
(1) The suit was brought twenty-five years after the original certificate was issued.

a. The suit is barred by laches because it was brought twenty-five years after the original certificate was issued.

The rules for traditional outlining call for outlines to begin with Roman numerals (I, II, III) and to proceed through letters (A, B, C, and a, b, c) and Arabic numerals (1, 2, 3). If you supplement those levels with Romanettes (i, ii, iii), and parentheses ((a), (b), (c) and (1), (2), (3)), you can create an outline with 7 levels: I. A. 1. a. (1) (a) (i). Two suggestions.

First, don’t write a document (motion, brief, or even a contract) that needs seven levels of headings. Find a way to condense and consolidate; strive to limit yourself to four or even three levels. You’ll be less likely to lose your reader—and yourself.

Second, if you know any level of your outline will go beyond six or seven items, consider using Arabic instead of Roman numerals or romanettes for that level. Roman numerals get harder to decipher the higher they go. I once read a lengthy contract divided into 60 major sections, each designated with a Roman numeral. It was difficult to refer to any particular article because it took too long (or became impossible) to figure out. What’s XLIV?

In my own outlines, I use Arabic numerals and the alphabet, and I still have four levels available: 1. A. (1) (a)

It’s 44 by the way.


To comment, email me.

A lesson in e-mail

“Dad, I just sent you an email I’m working on. Will you read it over for me? Remember the company I work for is selling its business at the Lexington location?”


“Well, the manager asked me to write an e-mail message to send to the customers to let them know about the ownership change and that they’ll be working with a new company, not us. Could you check it to make sure it’s grammatically correct and makes sense?”


“I need it in an hour.”

“Okay. I’ll go open it now.”

I read the message, which was about 8 paragraphs long. The tone was friendly, and the message was clear. The grammar was fine. I started to insert a few comments suggesting a few minor things. Then I read it again. It needs work on organization, I thought. It’s 8 paragraphs, which is a lot to ask someone to read in e-mail, but it didn’t flow—wasn’t well connected. Each paragraph was about a new topic, but there were no transitions. It needed something.

I stopped inserting comments and decided to rewrite it in a question-and-answer format, like FAQs. I created about 5 questions, and then I revised and moved the text around to form answers. For example, after an introduction announcing the change in ownership, I inserted a question:

Can I still have my event at the Lexington location?

Yes, . . .

Will the policies and prices be the same?

Yes, . . .

And so on. I was feeling quite proud of myself, and I sent the rewrite. I called the next day to ask how things had gone.

“Thanks, dad. Everyone liked the Q & A format, but they decided we should call each customer instead of sending an email.”


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