The jury of popular opinion is divided on the writing style of the newest justice on the Supreme Court. Slate pronounced Neil M. Gorsuch a terrible writer. But a forthcoming quantitative study of his published opinions concludes that he “does exceedingly well according to the standards of good writing that legal writing authorities espouse.” His writing is the subject of a mocking Twitter hashtag and has been covered in the New York Times.

Associate Justice Neil M. Gorsuch; photograph by Franz Jantzen, 2017.

But what do legal editing programs think of Gorsuch’s writing? There are several such programs available to lawyers. The most-popular ones operate as add-ins to Microsoft Word, performing grammatical and stylistic analyses of briefs, memoranda and other legal documents.

I decided to test Gorsuch’s opinions against three of these programs: BriefCatch, PerfectIt and WordRake. I had never before used BriefCatch. I had previously reviewed both of the other programs, calling PerfectIt a virtual, eagle-eyed proofreader, and twice testing WordRake against Supreme Court opinions, first against the writings of Justices Antonin Scalia and Elena Kagan, and then against Justices John G. Roberts Jr., Clarence Thomas and Stephen G. Breyer.

At the outset, it is important to note that these three programs operate differently and perform different functions. WordRake and BriefCatch are similar to each other in that they focus on enhancing clarity and concision. In contrast, PerfectIt is a proofreading tool; its suggestions are more granular and encompass punctuation, formatting, citation style, capitalization, and more.  WordRake and BriefCatch perform a one-time analysis — one calls it a “rake,” the other a “catch” — while PerfectIt performs a series of tests.

Texas v. New Mexico

I started with Gorsuch’s majority opinion in the water dispute, Texas v. New Mexico. This was the opinion in which Gorsuch “seemed to hit his stride” as a writer, Nina Varsava, author of the study of his opinions and both a Yale law student and Stanford doctoral candidate, said in the New York Times.

When I ran the three editing programs against this opinion, PerfectIt immediately caught something neither of the others did. One of its first tests looks for spelling variations, and it found the same word spelled two different ways, “mold” and “mould.” In this case, the variations were intentional. Gorsuch quoted an opinion that used “mould,” but in his own use of the word, he chose “mold.”

Another PerfectIt test, this one for capitalization, also caught something neither of the others did. It noted that the word “Compact” appeared in the opinion 24 times capitalized and four times not capitalized. It gave me the option of using one form or the other in all instances (or of leaving them as they were), but also warned to check the context, as words may need capitals in one place but not another. Here, the differences in capitalization were intended. Some referred to a specific compact by its formal name and thus were capitalized, while others referred the noun in its generic sense. PerfectIt also caught inconsistent capitalization of the words reservoir and state.

Unlike PerfectIt, BriefCatch and WordRake focus on enhancing concision and readability. With regard to Gorsuch’s opinion in the Texas case, both programs were sparse in their edits. A good example is the first paragraph, which some readers have praised for doing what opening paragraphs should do — draw in the reader.

BriefCatch made two suggested edits to this paragraph. First, it suggested changing “are made” because it is the passive voice. It did not provide rewording, but a sidebar suggested, “[R]ewrite in the active voice, focusing on the actor, not the action.” BriefCatch also suggested changing “In an effort to reconcile” to the more concise “To reconcile.”

WordRake made the same suggestion to shorten “In an effort to” to simply “To,” but it did not pick up on the passive voice.

Skipping over the next two paragraphs to the fourth, BriefCatch offered several suggestions. (Note that BriefCatch highlights text and shows the suggestions in a right-hand panel, whereas WordRake shows its suggested edits directly in the document.) BriefCatch suggested changing “before this Court” to “here.” It suggested that the phrase, “New Mexico filed a motion to dismiss,” be changed to “New Mexico moved to dismiss,” explaining that it is better to use “strong verbs” that are “short and sweet.” It recommended deleting “in pertinent part” as unnecessary and changing “a number of” to “many” or “several.” It suggested replacing “concerning” with a shorter word such as “about,” “for,” “over” or “as for.” It also suggested changing “violations of” to “violating,” changing “be permitted” from passive to active voice, and changing “to the extent they” to “if they.”

WordRake made some but not all of the same suggestions. It agreed on changing “filed a motion to dismiss” to “moved to dismiss,” getting rid of “in pertinent part,” changing “a number of” to “several,” and changing “concerning” to “about.” One suggestion it made that BriefCatch did not was to delete the phrase, “At the same time.”

Both BriefCatch and WordRake continued to make similar corrections throughout the opinion. Here is how BriefCatch edited the opinion’s final paragraph. For the phrases “are persuaded,” “be taken,” “is sustained,” “are overruled” and “is remanded,” BriefCatch suggested changing all from the passive to the active voice. It also suggested changing “in the absence of” to “without.”

WordRake made no mention of the paragraph’s frequent use of the passive voice and suggested a crisper edit to the “absence of” phrase, changing “in the absence of any of the considerations” to “absent the considerations.” It also made the nonsensical suggestion to change “Nothing in our opinion should be taken” to “Nothing should be taken.”

Artis v. District of Columbia

With Gorsuch’s writing in Texas v. New Mexico having come through these editing programs relatively unscathed, I decided to go back to his dissenting opinion in Artis v. District of Columbia. This was the opinion Slate author Mark Joseph Stern cited as an example when he wrote, “Gorsuch’s prose has curdled into a glop of cutesy idioms, pointless metaphors, and garbled diction that’s exhausting to read and impossible to take seriously.”

Both BriefCatch and PerfectIt were far kinder. Here again, BriefCatch tended to focus on instances of the passive voice and WordRake tended to look for opportunities to shorten sentences. This is illustrated in the first paragraph of Artis. BriefCatch seized on the passive voice in “was built.”

WordRake tried to shorten the paragraph, with nonsensical results. It wanted to change, “… sometimes all that means is we need to look more carefully for the reason it was built in the first place,” to, “… sometimes all that means is we need to look more carefully it was built.” Huh?

The two programs diverged in this next paragraph. BriefCatch disapproved of the passive “was commonly used” and wanted to change “in cases where” to “when.” It suggested changing “period of time” to either “period” or “time” and “in these circumstances” to “here,” “in that case,” or “in that event.”

WordRake ignored all of BriefCatch’s suggestions. Instead, it deleted the transitional phrases “by contrast” and “in this situation.” It changed “used in cases where” to “used where” and deleted “necessarily.” It changed “happened to sit” to “sat” and “suffice to allow” to “allow.”

The two programs made various other edits to the dissent, but they were all in the same vein and relatively innocuous from a critical perspective.

PerfectIt, as I mentioned, performs a unique set of tests. It noted right off that Gorsuch twice failed to hyphenate “common law” in the phrase “common law rule,” and suggested that hyphenation is preferred. It found the same omission in several other phrases, such as “state law claims.” It also found five instances where Gorsuch failed to capitalize the first word after a colon. It found numerous instances where words appeared both capitalized and uncapitalized, such as “Court” and “court” and “State” and “state.”

Henson v. Santander

Rather than continue with Artis, I decided to turn to a paragraph that has generated much critical comment, both favorable and disfavorable. It is the first paragraph in Gorsuch’s first majority opinion since joining the Supreme Court, Henson v. Santander. Scholar Varsava called its alliteration “showy and jarring.”

BriefCatch had no problem with the paragraph.

WordRake suggested two minor changes, deleting “that” and “exactly.”

Thus, neither BriefCatch nor WordRake were bothered by the justice’s showy alliteration.

Reading Happiness

BriefCatch provides two additional analyses that neither WordRake nor PerfectIt have. One is a set of five scores related to readability. (See this explanation.)  Here is how Gorsuch scored in the Texas case:

BriefCatch also provides a narrative report. Here was the report for the Texas case:


In the Artis dissent — the case Slate criticized — BriefCatch gave him a higher score than in the Texas case:

And here was the narrative BriefCatch gave for the Artis dissent:

In Henson, the opinion with the “showy” alliteration, BriefCatch gave Gorsuch the lowest overall score of the three opinions:

And here is the narrative it provided for Henson:

The Bottom Line

I performed this analysis in order to compare how different legal editing programs would handle the same documents. As you can see, PerfectIt is best used as a proofreader and best deployed before finalizing a document to check for errors and inconsistencies. Both BriefCatch and WordRake are also best used before finalizing a document, but for the purpose of tightening language and improving readability.

Use of all of these has to be guided by your own editorial judgment. Just because a program says you should do something, that doesn’t always mean you should. Otherwise, you might end up with a phrase in your document such as, “We need to look more carefully it was built.”



WordRake, the editing and proofreading add-in for Microsoft Word and Outlook that is designed for lawyers and other professionals, released its version 3 yesterday.

With more than 600 new editing algorithms and 900 enhancements to existing algorithms, WordRake 3 offers 25 percent more edits and even greater accuracy, according to a company announcement.

Version 3 also simplifies the interface to allow users to see all editing suggestions for an entire document with just one click of the Rake button. In previous versions, you would first select the portion of the text to rake. (You can still do this, if you want to check only specific text.)

I’ve tested previous versions of WordRake against some of the best opinion writers on the Supreme Court. To read those previous reviews, see:

I have not had a chance to do that with this latest version but I plan to in the near future.

WordRake was originally created specifically for lawyers by Gary Kinder, a lawyer and writer whose 1998 book, Ship Of Gold In The Deep Blue Sea, went to number seven on The New York Times bestseller list. WordRake “rakes” your documents in search of unnecessary and obtuse words, suggesting edits to improve clarity and concision.

According to yesterday’s press release:

WordRake 3 converts hundreds of dull nominalizations to lively verbs (“make a recommendation” becomes “recommend”), turns negative statements into positive statements (“the auditor didn’t find any discrepancies” becomes “the auditor found no discrepancies”), and removes windy “windups” (“It should be stated that” and “Please note that”).

I always urge that WordRake be used with a critical eye, reviewing each suggestion and considering whether it helps or hurts. The problem with any automated editor is that it has no brain. As I wrote in my initial 2012 review:

It is unable to discern meaning, context or color. In its mechanical application of rules, it risks changing the meaning of a sentence or phrase.

Still, I think it can be a useful tool for improving and tightening one’s writing. If nothing else, it forces you to think about your structure and phrasing. That alone can improve any written work.

The WordRake add-ins for Word and Outlook each cost $129 for a one-year license. Both can be purchased together for $199 for one year. A seven-day free trial is available through the WordRake website.


Clio now integrates with Vonage VoIP phone services.

Time to play catch-up on legal technology news and notes from the past few weeks:

Take credit cards in MyCase. The practice management platform MyCase already has the ability to accept online payments directly from a client’s checking account. At the recent ABA Techshow, MyCase announced that its payments feature will be expanded later this year to include a built-in credit card option. It will allow users to accept credit card payments through MyCase for a flat 3 percent transaction fee.

For a short video showing how MyCase Payments works, see here.

Clio gets new call services. Practice management platform Clio announced two integrations at Techshow that provide enhanced calling services for its users.

The first is an integration with the VoIP telephony company Vonage Business. The integration allows firms that use Vonage as their business phone system to have all incoming and outgoing calls automatically logged in Clio, showing each call’s date, time and duration. Once logged, the call can be associated with a contact or a matter and a time entry created. The integration also enables click to dial from within Clio.

The integration works with all phones — desk, softphones and mobile. It uses Vonage’s middleware product gUnify to connect Vonage and Clio. Because gUnify is cloud-based software, it works without any special hardware or software required of the law firm and can be quickly set up.

The second integration is with Ruby Receptionists, a company that offers live, remote reception services for the legal industry. With the integration, messages and voice mail notifications from Ruby are sent directly to a lawyer’s or firm’s Clio account.

And Lexicata now also integrates with Ruby. Lexicata, the cloud-based CRM and client-intake software for law firms, has also announced an integration with Ruby Receptionists.

Now, when a Ruby receptionist answers a call for your firm, he or she will be able to take down the caller’s name, email, phone number, and some basic call notes into a webform. The data will be captured into theLexicata Inbox and the firm will receive an email notification.

From there, the firm can “Quick Intake” the lead and set up a new matter in Lexicata with a couple of clicks. The call notes will be saved as a matter note, and their contact info will be pre-populated to really streamline the process.

Tackling legalese. No doubt many of you have heard of or even used WordRake, a legal-editing add-on for Microsoft Word and Outlook that can help tighten your writing. I’ve learned that the next release of WordRake, coming out later this year, will go even farther.

The next version will have two separate functions. One, called Clear and Concise, will do what WordRake now does. The new function, called Plain Writing, will tackle legalese, suggesting ways to eliminate obtuse and legalistic language.

If you’re not familiar with WordRake, see my reviews of version 1.0, in which I tested its ability improve the writing of Justices Scalia and Kagan, and version 2.0, in which I tested it against the plurality, concurring and dissenting opinions in McCutcheon v. Federal Election Commission.

A job board for legal tech. Evolve Law, a for-profit organization launched last September to help drive technology innovation and adoption in the legal industry, has introduced a job board.

The job board features job openings at Evolve Law member companies. Among the current listings are jobs at Abacus Data Systems, Allegory Law, Avvo, Contactually, CosmoLex, Hire an Esquire and LegalZoom.

In conjunction with the job board, Evolve Law plans to stage a series of career fairs around the country.

And also from Evolve Law. A new podcast, looking at innovation in the legal industry through interviews with company executives involved in legal startups.

A matching site for A2J projects. A2J Author is a tool used by legal aid programs, courts and others to create automated guided interviews to help direct individuals in need of legal help. (I previously wrote about it here.) Last week, A2J Author’s developer, the Center for Computer -Assisted Legal Instruction (CALI), announced the new A2J Project Matching Portal.

The portal helps connect legal aid organizations and courts that are looking for help creating A2J projects with teachers of A2J Author courses who are looking for student projects. An organization posts a project request to the site and law faculty browse available projects and contact any they are interested in helping with.

CongressDotGov is officially out of beta.

I’m always making notes to myself about items to blog about here but never have time to get to them all. Today, therefore, I offer some brief mentions of items I think are worthy of mention.

Lawyers and their hobbies. I just discovered Hsu Untied and I love it. It is a podcast by Silicon Valley technology lawyer Richard C. Hsu in which he talks with lawyers about hobbies they pursue outside of law. You’ll hear about the senior litigation counsel at Apple who pursues astronomy in his free time, the UC Hastings Law School dean who has a passion for Honda Hawk motorcycles, and the legal recruiter who moonlights as a standup comedian.

Learn e-discovery free. The folks at e-discovery company Logikcull recently announced that they are offering a free e-discovery “sandbox” to anyone who wants to learn more about how e-discovery works. The sandbox is prepopulated with 100MB of data so that lawyers can learn about metadata, de-duplication and other aspects of e-discovery. To get started, just sign up for a free sandbox account.

Free federal rules ebooks. The Center for Computer-Assisted Legal Instruction, better known as CALI, has released updated versions of its free federal rules ebooks, Federal Rules of Evidence, Federal Rules of Civil Procedure and Federal Rules of Criminal Procedure. CALI publishes these in cooperation with the Legal Information Institute at Cornell Law School. They are in EPUB formats available free for anyone to download.

Legal IT blog. The folks who run the digital forensics and IT consulting firm Sensei Enterprises, Sharon Nelson and John Simek, are well known in the legal community for their frequent speaking and writing. Sharon has long written one of the best blogs out there on electronic evidence and information security, Ride the Lightning. Now, John has launched a blog of his own, Your IT Consultant, where he is covering a range of IT topics, from hardware to networks to security. Check it out. out of beta. Two years ago, I wrote here about the beta launch of, a new site for U.S. legislative information that would eventually replace the aging site. Last week, officially came out of beta and also announced additional enhancements, including a new Resources section that provides an A-to-Z list of hundreds of links related to Congress, including help pages and research guides. If you’re not sure where to start with a research issue relating to Congress, here’s the place.

Indigenous law. Speaking of Congress, the Law Library of Congress recently unveiled an Indigenous Law Portal that collects and organizes resources and materials related to tribal law in the United States.  The portal features a map of the country on which you can click to find materials related to tribes within specific states. If you are researching issues that involve tribal legal matters, this is where you start.

WordRake for Outlook. I’ve twice reviewed WordRake, the Microsoft Word add-on that proofreads your documents. (See my reviews here and here, testing it against some of the profession’s most eloquent writes, the justices of the Supreme Court.)  Now, WordRake is out with a version for Outlook that suggests edits to your email before you hit the send button.

That wraps up our round-up for this Friday. Have a great weekend.

When WordRake , the editing program for lawyers, was first released in 2012, I put it to the test against two of the most eloquent writers on the Supreme Court, Justices Antonin Scalia and Elena Kagan. If WordRake could improve on Scalia and Kagan, I reasoned, imagine what it could do for the rest of us.

Now, WordRake is preparing to release version 2.0 of its software and it provided me with a beta version. This time, I decided to give Justices Scalia and Kagan a rest, so I turned to the Supreme Court’s controversial recent opinion in McCutcheon v. Federal Election Commission. The case provided the opportunity to test WordRake against the writing of three justices: the plurality opinion by Chief Justice John G. Roberts Jr., the concurring opinion of Justice Clarence Thomas and the dissent of Justice Stephen G. Breyer. Continue Reading We Test WordRake’s Beta Version 2.0 on ‘McCutcheon’

WordRake is a new editing program created specifically for lawyers. An add-on to Microsoft Word, it “rakes” your documents in search of unnecessary and obtuse words, suggesting edits to improve clarity and concision. It is the creation of Gary Kinder, a lawyer and writer whose 1998 book, Ship Of Gold In The Deep Blue Sea, went to number seven on The New York Times bestseller list.

What better way to test WordRake, I decided, than to use it on two of the most eloquent writers on the Supreme Court, Justice Antonin Scalia and Justice Elena Kagan. Together with Bryan A. Garner, Scalia is the author of two books about legal writing, Reading Law: The Interpretation of Legal Texts, and Making Your Case: The Art of Persuading Judges. Kagan received praise from Jeffrey Rosen in The New Republic for her “emergence as an eloquent voice” on the court. As an example, he cited her dissent in the 2011 case, Arizona Free Enterprise Club v. Bennett.

If WordRake could improve on Scalia and Kagan, imagine what it could do for the rest of us, I thought.

Rosen calls Scalia the court’s “most dazzling writer.” To illustrate his point, he quotes a sentence from Scalia’s concurring opinion in the 1993 case, Lamb’s Chapel v. Center Moriches School District.

Like some ghoul in a late night horror movie that repeatedly sits up in its grave and shuffles abroad, after being repeatedly killed and buried, Lemon stalks our Establishment Clause jurisprudence once again, frightening the little children and school attorneys of Center Moriches Union Free School District.

Taking my cue from Rosen, I pasted Scalia’s Lamb’s Chapel concurrence into a Word document and ran it through WordRake. First, I downloaded the free, three-day trial of the software and installed it in Word. This takes just a few moments, after which WordRake appears on the Word menu. Highlight a selection of text, select “Rake” from the WordRake menu, and the program begins to scan the document. When it is done, you can review its suggestions and accept or reject them.

Here you see WordRake’s treatment of the opening paragraph of Scalia’s concurrence:


 Here, WordRake has succeeded in improving Scalia’s prose. It deletes both “generally” and “in this regard” as unnecessary words. It smooths out “a violation of” to “violating” and does the same for “the showing of” to “showing.”

In this next example, WordRake does not perform as admirably.


Several of WordRake’s suggestions here are simply wrong. In the first line, it changes “the proposed use of the school’s facilities” to “the proposed the school’s facilities.” Later, it changes, “That was not the view of those who adopted our Constitution,” to, “That was not adopted our Constitution.” Then, it changes, “It suffices to point out that,” to, “It points out that.” Other changes are more matters of style than of wrong or right, such as deleting “then” from the phrase, “Unsurprisingly, then, indifference ….”

I decided to try another Scalia sample, the majority opinion in the 2008 Second Amendment case, District of Columbia v. Heller. After reviewing the roughly 17,000-word opinion, WordRake was fairly modest in its suggestions for Scalia. Many of the suggestions were repetitive, such as changing every instance of “insofar as” to “where,” “the use of” to “using,” and “makes clear” to “clarifies.”  In at least one instance, WordRake’s suggestion changed the meaning of the phrase.


Where Scalia wrote, “Since those discussions took place 75 years after the ratification of the Second Amendment, they do not provide as much insight into its original meaning as earlier sources,” WordRake would change that to, “Since those discussions took place 75 years after the ratification of the Second Amendment, they provide as little insight into its original meaning as earlier sources.” Scalia is saying that the earlier sources provide greater insight but WordRake puts the earlier and later sources on a par in providing “little insight.”

For Kagan, I again took my cue from Jeffrey Rosen, testing WordRake using her dissenting opinion in Arizona Free Enterprise. WordRake uncovered no major “gotchas” in Kagan’s writing. The following paragraph is a good example of its review:


These are stylistic judgment calls. Do you want to say, “The difficulty, then, is …,” or, “The difficulty is …”? What about, “In short, the dynamic nature,” versus, “The dynamic nature …”? WordRake cuts words of transition that, while not necessary, arguably help the flow. WordRake is correct in pointing out that “the amount of money needed” can be shortened to “the money needed,” but it is wrong in suggesting the deletion of “effectively” in the last line.

WordRake does make some minor improvements to Kagan’s prose. Among its suggestions are to change “does not restrict any person’s ability” to “restricts no person’s ability”; “subsidies … do not restrict any speech” to “subsidies … restrict no speech”; and “who presumably would not be able to” to “who presumably could not.” It regularly deletes transitional phrases such as “for this reason” and “to the contrary.”

Fearing that I had not been fair to WordRake by pitting it against two of the legal profession’s most accomplished writers, I decided to try it on a random contract. I went to the wireLawyer site that I wrote about last week and found a 124-page El Pollo Loco franchise agreement. I downloaded it as a Word document and ran it through WordRake.


Above is a typical paragraph, as edited by WordRake. The more you use the software, the more you see how it works. It searches for phrases lawyers often use — such as “in addition to,” “pursuant to” and “in accordance with” — and suggests simpler words such as “besides” and “under.” It is programmed with a set of usage and grammar rules and applies those rules to the document.


Above is another example from the franchise agreement. The suggestions are mostly improvements, but note that the final deletion would alter the meaning of the sentence.

WordRake does not have a has no brain. It is unable to discern meaning, context or color. In its mechanical application of rules, it risks changing the meaning of a sentence or phrase.

Still, WordRake was able, in some instances, to improve the writing of linguistic legal luminaries Scalia and Kagan. If it can help them, chances are it can help you. The important lesson from the above examples is to use WordRake with a critical eye. Review each suggestion and consider whether it helps or hurts. Clearly, it is capable of doing either.

WordRake is sold on a subscription basis. A one-year subscription is $99. Quantity pricing is available. As I noted at the outset, you can download a three-day free trial.

In my opinion, at $99, WordRake is sensible purchase. Think of it as an extra layer of review for your writing or even as a sort-of robotic writing teacher. See its suggestions for simplifying text often enough and they may become second nature. Use it for a year and, who knows, you may learn enough that you will not need a second year.