(Plain text legal on hold for a little bit due to paying legal work)

The other thing to keep in mind is that Markdown (including MultiMarkdown) allows you to include raw HTML elements. For example: If you need a line break inside a table cell, you could just type <br> to get what you need.

MultiMarkdown metadata is an interesting addition to a plain text legal workflow. It could allow you to more easily use templates, or specify the court for a pleading, resulting in appropriate formatting for the specific jurisdiction.

Because MultiMarkdown is based on Markdown, which was designed to generate HTML, there is no easy way to apply page-based formatting. This presents a problem when courts require footers or line numbers. But LaTeX may provide an answer.

*Ironically, some of the most traditional caption blocks are relics of the plain text typewriter era, when the table boxes were literally drawn with parentheses, dashes, colons, or other characters.

A caption block in MultiMarkdown is challenging. Essentially, it’s just a two-cell table. But MMD needs HTML to allow line breaks within a cell. And MMD doesn’t have a mechanism for specifying which table borders are visible.

Legal citations are a major challenge in MultiMarkdown.

MultiMarkdown allows for citations, but it’s focused on academic citations, rather than legal citations. And it’s not clear whether these citations can be adapted for legal purposes.

In MultiMarkdown, the syntax for marking up citations is fairly straightforward: [citation text][#cited source nickname] followed by (somewhere) a [#cited source nickname]: Full Source Name. (You could also add the full source inline, but that can get unweildy).

The difference between academic and legal citations is important. In legal writing, the source is usually explicit and included right in the text itself. E.g., ABC Inc. v. XYZ, LLC, 123 F3d 456, 458 (13th Cir. 2025). And that case (or statute or rule) is listed in the Table of Authorities, with a reference indicating on which page or pages it appears.

Ideally, we’d like to mark that up as follows:

(in the table of authorities):

[#ABCvXTZ]: _ABC Inc. v. XYZ, LLC_, 123 F3d 456 (13th Cir. 2025)....[page number(s)]

(in the text):

[_ABC Inc. v. XYZ, LLC_, 123 F3d 456, 458 (13th Cir. 2025)][#ABCv.XYZ].

In short, a Table of Authorities is a one-to-many listing, where you start with the “one,” and use it to look up the “many.”

Academic citations are the opposite. While there is still only a single source listed in an academic bibliography, the text contains multiple citations. As you read a paper, you may want to tap on the citation to see the full source citation. But you don’t start with the bibiliography and work backwards. Academic bibliographies are a many-to-one listing, and it does not appear capable of generating links back to the places in the text that a given source is cited.

The academic equivalent of a table of authorities would be something more akin to an index than a bibiliography. But, alas, there is no “index” equivalent in MMD, (other than a table of contents for headings).

Still, at a meta-level, the MMD syntax for citations gives us nearly everything we would need to generate a table of authorities. So perhaps we can do some processing of a MMD file to get what we need.

MultiMarkdown footnotes work just fine.[^Though if you don’t do in-line footnotes, you may have to keep track of the names/numbers yourself.]

MultiMarkdown tables are pretty basic, so any styling you might need (eliminating some of the borders, etc.) will need to be added later.

MultiMarkdown headings for contracts can also be tricky because there is no direct way to indicate whether or not the headings should be numbered, or how that numbering should work. (1.1.4 v. I.A.1.a etc.)

MultiMarkdown signature blocks are not all that difficult. The hardest part is getting nice signature lines. Escaping underscores seems to be the easiest way, though getting the right number remains a challenge.

Towards a legal markup language

Court-mandated styles may require adding:

  • line numbers (reset by page)
  • footers with document title and counsel information
  • caption blocks with court names, case numbers, titles, and party names).

Towards a legal markup language

Starting simply: what markup do we need for contracts?

  • Sections, subsections, subsubsections
  • Cross references
  • Signature blocks
  • A table or two (maybe)

That’s really about it.

To take a step back, a plain text legal solution must:

  1. Use markup that gives easy access to most semantic elements a lawyer needs to write.
  2. Add a styling language or template that interprets 1 and adds any missing components.

MultiMarkdown adds several key abilities to a plain text legal workflow:

  • tables
  • footnotes
  • cross references
  • tables of contents

Each has limitations, at least in its MMD form. (Just try making a case caption block in MMD.)

Potential components of a plain text legal solution:

  • Multi-Markdown
  • git
  • pandoc
  • LaTeX
  • Racket/Pollen
  • scripts (javascript or python)

I don’t think all of those will be needed. But they might be.

LaTeX is too complex for lawyers to adopt

Where Markdown is not sophisticated enough, LaTeX is too complex for lawyers to make a habit of writing in it everyday. We need to marry Markdown’s ease of use with LaTeX’s layout power.

Markdown isn’t enough for plain text legal documents.

Markdown is meant to be an easy way to write basic HTML using minimal, human-readable markup. And it’s great. But more is needed to get proper, paginated, rich-text legal documents.

One solution: Just paste plain text into Word, and apply a set of pre-defined styles saved in a blank template. This works, but is tedious, time consuming, and error prone. (But I’ll admit that this is sometimes the best way to reformat a .docx with hopelessly FUBAR’d formatting.)

Any solution for using plain text for legal work must: (1) allow us to convert plain text to paginated, rich-text final documents; and (2) do so in a way that doesn’t destroy the advantages of working with plain text in the first place.

Challenge No. 3 of using plain text for legal work:

Collaborating. Your colleagues, co-counsel, opposing counsel, clients, and even the courts all expect you to use .docx for editable documents.

Challenge No. 2 of using plain text for legal work:

The end product must be paginated. Legal documents include header, footer, page number, table of contents and of authorities, margin, font size, and even line number requirements.

Challenge No. 1 of using plain text for legal work:

The end product must still be rich text. A contract to be signed; a brief to be filed. All require some amount of styling to be easily read. Plain text doesn’t provide that inherently.

Reason no. 5 to prefer plain text to .docx for legal work:

Plain text is a common denominator. Almost any tool can generate plain text. CLI/GUI/dictation/scribbling on an apple watch. You don’t have to worry about compatibility.

Reason no. 4 to prefer plain text to .docx for legal work:

Archiving is better. Plain text files will be just as usable, readable, and searchable in 10 years as they are today. (RIP .doc, .wpd, etc.)