How to Lose a Judicial Law Clerk in 10 Ways
Judicial law clerks serve a necessary function in the daily work of Florida’s courts. Justices and judges could not perform their duties without the assistance of their law clerks. One of the many duties of a law clerk is to review, summarize, and memorialize the briefs in cases assigned to their jurists’ chambers. Law clerks are, therefore, a liaison between advocates and the judiciary. As an appellate advocate, it is your duty to ensure that those who are among the first to read your brief are not immediately dissuaded by your stylistic choices. As former law clerks ourselves, our goal is to point out the most frequent offenses. Much like Kate Hudson’s Andie in the movie, How to Lose a Guy in 10 Days, do the following at your own peril — not everyone is Matthew McConaughey.
• Fail to Abide by the Clear and Simple Rules of Appellate Procedure — You are probably questioning why this one is here. It is simple — follow the rules! You would be surprised how many writers of briefs fail to follow the basic rules set forth in the Florida Rules of Appellate Procedure. For example, we have seen briefs that change to a different font in the middle of a sentence despite the clear and simple rule that “[c]omputer-generated briefs shall be filed in either Times New Roman 14-point font or Courier New 12-point font.”
Another rule provides that the initial, answer, and reply briefs must contain a “[t]able of contents listing the sections of the brief, including headings and subheadings that identify the issues presented for review, with references to the pages on which each appears.” We have seen briefs that have incorrect page references or no page references at all.
We realize these may seem trivial, but consider it from our perspective. The law clerk’s day is spent reviewing briefs and the record to discern what happened. You are our guide. We need you because we were not there. But, we need your assurance that you know what you are talking about. The easiest way to get us to doubt you is to be cavalier about the rules.
• Make Arguments in the Fact Section — Your advocacy begins in the facts section. Be sure to include as many asides, footnotes, and aspersions as you can to ensure you do not omit a single argument. Why should your fact section merely be a recitation of the facts of the case in nearly chronological order? Why should you tell a story when you could make additional arguments? Why should you bypass an opportunity to slam the opposition? Why? Because it undermines your credibility. Law clerks do not begin their review of a case biased toward a party or an idea. We tend to pride ourselves in our ability to be neutral and see both sides of any case. That said, it is human nature to question the veracity of any fact that is not supported by a record citation or is not stated as directly and succinctly as possible. Once the question enters a law clerk’s thought process, that law clerk will inevitably begin to search for the answer to that question whether it can be found in your brief, opposing counsel’s brief, or the law clerk’s independent research.
In our opinion, it best serves your client and the court when your facts section helps set out the facts of your case in the best possible light to your client. Omitting facts or including arguments within the facts section makes it more difficult for the law clerks and, ultimately, the court to understand the case. The court does not review the case in a vacuum — it will have access to opposing parties’ briefs, the record, and the law clerk’s independent analysis. While it is helpful to frame the argument and provide your version of the story, you do not want a law clerk spending too much time simply attempting to understand what happened before turning to the legal question your case presents.
• Reinvent the Wheel — Think back to when you were in elementary, middle, or high school. How many times were you told to put something “in your own words?” This is ingrained in us early on. We are here to tell you that it does not have to — and maybe should not — be that way. We are not telling you to file a brief full of block quotes. In our experience, block quotes, particularly when they span multiple paragraphs, generally are ineffective. The reader almost always glosses over the block-quoted text, looking for when the regular text begins again. If you are relying on a well-established legal standard, quote the relevant language from the case you are citing. There is no need to try to restate it in your own words. Why? You may end up stating it incorrectly, which can have the unintended effect of making your law clerk think you are being disingenuous.
As lawyers, we all know that words matter. How many times has the crux of your case turned on whether the applicable statute used “shall” instead of “may?” Judges and their law clerks are particularly fastidious about word choice because they have to be — opinions become precedent. We encourage you to be fastidious as well. Instead of trying and potentially failing to correctly state a legal standard, statute, or rule in your own words, just quote directly from the source. We promise you will not lose any creativity points.
• Be Overly Clever — Every lawyer believes himself or herself to be clever. Exhaust your use of that cleverness in your writing. Law clerks enjoy little more than reading belabored analogies, bad puns, and citations to esoteric bits of media. If your brief does not require a law clerk to head to the library or refer to Google, you have not tried hard enough. Extra points to any attorney who causes judicial staff to circulate excerpts of your brief among themselves for much-needed levity.
In all seriousness, your goal as an advocate is to produce a readable, informative document that best explains your client’s argument to the court. As Bryan Garner reminds us, “In legal writing as in all writing, the object is to communicate effectively.” Analogies, puns, and references are only as good as they are helpful. Your baseball analogy that requires expert knowledge of the inner workings of the relationship between management and owners will be ineffective for anyone who does not closely follow baseball.
Effective advocacy explains your client’s story of the case in a way that draws your reader’s attention, clearly explains why the law supports your client’s perspective and provides distinguishing characteristics for any cases or facts that do not work in your favor. Any analogy used should help illustrate your case to the average person. Making an analogy to an 11 o’clock number would be missed by anyone not interested in musical theater. Likewise, an analogy to a particular sport is lost on those who do not follow that sport. Using a $10 word when a nickel would do does not strengthen your argument, but being careful with your language when necessary will.
• Provide Incorrect and Inconsistent Citation Usage — Citations should be absolutely impossible to locate. When you cite the record, you should refer to documents in your own, personal jargon and use an unnamed numbering system. You should ignore Florida Rule of Civil Procedure 9.800 and create your own citation style and vary it throughout your document. Instead of providing the case name, number, and a reporter citation, you should only give a single company’s database citation. If a court has not provided you with the language that you need, or even if you are pretty sure the court said it somewhere in something you have read before, you should provide the quotation and just guess where it may be.
Please do not do any of this. Look, we get it. Citations can be difficult. You have taken notes from scores of sources and cut and paste so many times when editing your document that you cannot easily realign your short citations to their full citations; or you quoted a portion of a case and are not sure whether the quote ran to the next printed page. Citation styles vary from Bluebook to the Association of Legal Writing Directors Guide to Legal Citation to the Chicago Manual of Style and you have learned one form only to be asked to use a different one. Even The Bluebook arbitrarily seems to change its citation styles from version to version. No court expects perfection, but everyone benefits from being able to find your sources readily and easily.
Your opposing counsel, the court, and you may each only have access to a single legal database, and you may all be using a different provider. If you only have access to Westlaw, the following citation is nearly useless: 2011 Fla. LEXIS 2641. Florida Rule of Appellate Procedure 9.800, Uniform Citation System, is the appropriate citation style for all Florida courts. As we have stated, following the clear and simple Florida Court Rules should always be in the forefront. As provided within the rule, it “applies to all legal documents, including court opinions.” Unless your citation is not listed within the rule, there is no need to refer to either The Bluebook or The Florida Style Manual.
• Overuse Typographical Emphasis — When we speak, we rarely speak in monotone. Accordingly, we sometimes wish to convey our spoken tone within our writing. Whenever possible, allow your writing to provide emphasis instead of using typographical emphasis to create it.
If you need to emphasize a sentence in a paragraph of block quote, consider using the sentence as a quote instead of the entire paragraph and trust that your reader will either look up or understand the context of the quote. Alternatively, block quote the entire paragraph, but then begin a new sentence with the portion of the quote you want to emphasize.
Likewise, “never” use quotation marks for emphasis or sarcasm in a court document. If the language inside the quotation marks is not a quote from someone or some document that is able to be cited, do not use them because it signals to your reader that the word used is inaccurate, incorrect, or untruthful. As an example, in the first sentence in this paragraph, the quotation marks around the word “never” imply that we do not really mean never, and that you may occasionally use “scare quotes.” We do not mean that. The use of scare quotes casts aspersion and doubt on your argument, an effect that you certainly do not desire.
• Use Headings Ineffectively — Some attorneys are masterful with their use of headings and subheadings. For example, Justice Cantero’s use of wit and pop culture references combined with usefulness and clarity in his specially concurring opinion in Windom v. State, 886 So. 2d 915, 935-52 (Fla. 2004) (Cantero, J., specially concurring). However, poorly placed or badly worded headings can lead to greater confusion. If your argument relies on a law clerk or judge reading your headings, it may be overlooked. Likewise, if your headings make it appear that your argument is something other than it is, you could inadvertently mislead the court.
Additionally, just as the phrasing of a heading can create confusion, transitioning to a different topic within a heading may result in your argument being overlooked or misunderstood.
For example, imagine you are advocating against a revision to the Florida Constitution because you believe that the provision violates the single-subject requirement. Which heading is clearer? 1) The Proposed Amendment Violates the Single-Subject Requirement; or 2) Because the Proposed Amendment Applies to Several Subjects, it Violates Article XI, Section 3 of the Florida Constitution.
Both versions ostensibly say the same thing, but one requires knowledge of the reference and lends itself to typographical errors and unintentional references. Well-executed headings can be useful for organizing your argument and assisting the reader. If you choose to use them, take the time to ensure headings are clear, concise, and correct.
• Fail to Edit — We are intimately familiar with the general rule that initial and answer briefs may be up to 50 pages. But — and we cannot overstate this enough — they do not have to be. Longer is not better. The person who writes the longest brief does not win. In fact, it may have the opposite effect.
Consider this scenario: Your brief is 47 pages long. The last 10 pages or so are devoted to restating points you have already argued, with one exception. Buried on page 45 is a point you are making for the first time. Unfortunately, the law clerk has zoned out due to the unnecessary repetition and misses the new point.
You are probably cursing us for suggesting that a law clerk could miss your winning argument because they zoned out. But, just like you, law clerks are busy. Yours is not the only case they are working on at any given moment. Law clerks are susceptible to losing focus just like anyone else. In our experience, the best briefs make a point without belaboring it.
With that in mind, we offer the following suggestions. If you can, have someone else read your work and — this next part is crucial — be open to their edits. Another option is to step away from it for a few days. Coming back with a fresh set of eyes can do wonders for shortening a lengthy brief and, more importantly, ensuring your arguments are clearly and succinctly communicated. Furthermore, editing your brief using either method, or both, will allow you to find any misstatements or mischaracterizations. No one wants to lose a case on a slipped “not.”
• File a Reply Brief Solely to Reiterate Points Argued in the Initial Brief — You have already filed the initial brief. Now you are just waiting for opposing counsel to file his or her answer brief. In fact, you have saved a few arguments in reserve for this moment. Then it arrives. You rifle through the answer brief, muttering every possible retort. You have to respond! That is what the reply brief is for! Not necessarily. “The reply brief shall contain argument in response and rebuttal to argument presented in the answer brief.” The reply brief should not be used, or abused, as a vehicle to reiterate what you have already stated or have the last word. In our experience, the best reply briefs are written with this understanding and purpose in mind.
One example is the following: In a criminal appeal, the defendant raised four issues. In the reply brief, with respect to the second issue, counsel responded to specific arguments made in the state’s answer brief. However, with respect to the first, third, and fourth issues, counsel simply stated that he relied on the arguments made in the initial brief. This is how it should be.
You have to zealously advocate on behalf of your client, but law clerks read everything you file. Just because the answer brief is filed after the initial brief does not mean that law clerks will forget all the extremely valid arguments raised in your initial brief. Save the reply brief for its intended purpose. And while we are on the topic, do not hold arguments until the reply brief. If you have an argument, make it in the initial brief. As former law clerks, we cannot tell you how many times persuasive arguments are raised too late.
• File Supplemental Authority That is Neither New Nor Supplemental — It is the day before oral argument in your case. The briefs were filed months ago and now you are just waiting for your moment to shine behind that podium. Alas, something is missing. You remember that you forgot to cite Marbury v. Madison, 5 U.S. 137 (1803). How is the court going to know its role without that case? No worries, you will just file a notice of supplemental authority the day before oral argument. You are doing the court a favor, you tell yourself.
You are not doing the court a favor. Not only are you disrupting the court’s preparation the day before oral argument, you are ignoring the purpose of the rule. Perhaps worse, you are doing yourself no favors with the clerk who is inevitably involved in his or her judge’s preparations and who now has to deal with your notice of supplemental authority that is — under no circumstances — supplemental.
“Notices of supplemental authority may be filed with the court before a decision has been rendered to call attention to decisions, rules, statutes, or other authorities that are significant to the issues raised and that have been discovered after the last brief served in the cause.” Note this part of the rule: “and that have been discovered after the last brief served in the cause.” You did not discover, or at least should not have discovered, Marbury v. Madison after the last brief was served. In all likelihood, it was one of the first cases you were taught in your first year of law school.
Marbury v. Madison is a drastic example. However, the point remains. If you are considering filing a notice of supplemental authority, particularly the day before oral argument, stop and ask yourself: Is it 1) truly supplemental, and 2) absolutely crucial for your case. If it is not, we would advise against it.
The preceding guidelines have been just that, guidelines. We are merely two former law clerks with a combined 15 years of experience in two different courts with a combined five jurists. As with any style guide, there is a time to abide and a time to deride. We sincerely hope our thoughts are cause for the former.
 Hat tip to How to Lose a Guy in 10 Days (Paramount Pictures 2003).
 The naming conventions for judicial law clerks vary by court and jurisdiction. The Florida Supreme Court, for example, calls law clerks “staff attorneys” once they are licensed to practice law. We both served as staff attorneys but for the purpose of this article, we will use law clerk to refer to either.
 For more information about the role of law clerks in the Florida Supreme Court, listen to the podcast, Beyond the Bench, The Suite Life: A Behind-the-Scenes Perspective (June 7, 2008), available at http://flcourts.libsyn.com/the-suite-life-1.
 Fla. R. App. P. 9.210(a)(2).
 Fla. R. App. P. 9.210(b)(1).
 See, e.g., The Fla. Bar v. Trazenfeld, 833 So. 2d 734, 738 (Fla. 2002) (“The word ‘may’ when given its ordinary meaning denotes a permissive term rather than the mandatory connotation of the word ‘shall.’”).
 A majority of cases are won or lost on the briefs alone. Oral argument is important but it is only rarely dispositive. See Warren D. Wolfson, Symposium: Oral Argument: Does it Matter? 35 Ind. L. Rev. 451, 454 (2002) (“[Oral argument] changes or makes up minds in about five to ten percent of the cases where we hear oral argument.”).
 Bryan A. Garner, The Elements of Legal Style 30 (2d ed. 2002).
 See Gallagher Law Library, Bluebook 101, http://guides.lib.uw.edu/law/bluebook101/updated_edition.
 Here is where we give you the full citation so you can marvel at how much easier it is: In re: Amendments to the Fla. Rules of Appellate Procedure, 74 So. 3d 239 (Fla. 2011).
 Fla. R. App. P. 9.800.
 Merriam-Webster, Scare Quotes, https://www.merriam-webster.com/dictionary/scare%20quotes.
 Fla. R. App. P. 9.210(a)(5)(B). Of course, a different rule applies to special cases. See Fla. R. App. P. 9.210(a)(5)(C).
 Cleverness is not always dexterous.
 Fla. R. App. P. 9.210(d).
 See J.A.B. Enters. v. Gibbons, 596 So. 2d 1247, 1250 (Fla. 4th DCA 1992) (“[A]n issue not raised in an initial brief is deemed abandoned and may not be raised for the first time in a reply brief.”); see also D.H. v. Adept Cmty. Servs., Inc., 43 Fla. L. Weekly S533 *6 (Fla. Nov. 1, 2018).
 Fla. R. App. P. 9.225.
 There are numerous style guides available for attorneys and judges. Some of the ones on our shelves include The Elements of Legal Style; Ross Guberman, Point Made. (2d ed. 2014); Richard C. Wydick, Plain English for Lawyers (4th ed. 1998); Ruggero J. Aldisert, Opinion Writing (1990).
This column is submitted on behalf of the Appellate Practice Section, Nicholas Ari Shannin, chair, and Thomas Seider, editor.