Daughter of the Empire State: Lessons in Legal Writing from New York Chief Judge Judith S. Kaye

By Gerald Lebovits

May 11, 2021

Daughter of the Empire State: Lessons in Legal Writing from New York Chief Judge Judith S. Kaye


By Gerald Lebovits

Judith S. Kaye[1] was born in 1938 in rural Sullivan County, New York. Forty-five years later, Governor Mario Cuomo appointed her associate judge of the Court of Appeals, New York’s highest court.[2] A decade later, in 1993, Kaye took charge of the court—and with it New York’s court system—as the court’s first female chief judge.[3] From Monticello High School through her retirement from the judiciary in 2008, Kaye established herself as a litigator, a firm partner, and a prescient judge.[4] Her opinions, majorities and dissents alike, survive with a clarity and force typical only of America’s greatest judges.[5] Her familiarity with the law was complete, even at home: Stephen Rackow Kaye, her husband of 42 years with whom she had three children, was a Proskauer Rose partner who wrote “the definitive work on commercial litigation in New York State.”[6]

The chief judge was respected across the nation. President Bill Clinton considered her both for attorney general and to fill the Supreme Court seat left open by Justice Byron White’s 1993 resignation.[7] Kaye declined both positions, citing her post as chief judge—at the time, less than one month old and yet, in her words, a “commitment and responsibility” and “magnificent opportunity.”[8] She would spend the next 23 years making good on that commitment. She asked of herself and the entire state, “[H]ow can we do better?”[9] Her consequent administrative and logistical remodeling of the New York court system was, like her jurisprudence, a testament to her thoughtful, systematic, and thorough nature.

Kaye was also a scholarly writer with an effective—and affecting—pen. The consummate New Yorker, she tried throughout her career to publish in as many New York legal publications as possible.[10] The written word was a natural refuge for the judge, who had a “lifelong desire to be a world-class journalist.”[11] After editing her high school newspaper and serving as editor-in-chief of Barnard College’s campus Bulletin, Kaye began her career reporting for the Hudson Dispatch out of Union City, New Jersey.[12] Only the “thought that a law degree would enhance her chances of becoming an international reporter”[13] compelled Kaye to attend New York University School of Law, her beloved alma mater. The lessons of journalism, no less than the experience of law, informed her every written work. “[M]y success in law school,” she said, “was largely attributable to skills I honed as a journalist, like diagnosis—what are the core issues, what’s most important, what’s the lead paragraph—and clear, articulate expression in the English language.”[14]

Kaye’s articles, essays, and speeches tackled issues ranging from state constitutionalism and jury reform[15] to women’s progress in big law firms[16] to legal education and scholarship.[17] She inspired significant revisions to New York’s official legal-style manual, the Tanbook,[18] and was America’s leading advocate for gender-neutral language in the law.[19]

Sometimes the subject of Kaye’s writing was legal writing itself.[20] But perhaps even more varied than the subject matter of her writings is the style: “Some of her articles are highly theoretical, some are intensely practical, some are intensely personal.”[21] At all times, though, her writing is lucid and accessible. It’s hard enough to convey one complex point in one writing style. Yet from the beginning to the end of her career, Kaye succeeded in conveying complex points in different styles, each precisely chosen and perfectly suited to the issue that prompted her publication. Words, to Kaye, are “critical to the practice of [law]; the better used the better the practice.”[22] Few used them better. By the time of her death in 2016, Judith Kaye’s words had not only furthered the law, but also taught others—from students writing papers[23] to judges writing opinions[24]—how to do just that. Not bad, the Chief Judge might say, “for a girl who grew up in Monticello.”[25]

Here’s what the chief judge wrote about legal writing.

Know your case; know your audience

It hardly seems necessary to underscore the importance of written and oral communication in the law—especially for the audience gathered here this afternoon.”[26]

Kaye understood that legal writing is often meant to persuade and that persuasion comes in different flavors. Lawyers seek to persuade courts to adopt this rule of law and reject that one; judges seek to persuade readers of their opinions that their decisions are correct.[27] Authors of law review articles seek to shape what lawyers and judges do.[28] Even if they advance the same position, the advocate’s argument before the bench should not resemble the academic’s argument before a committee of student journal editors. At all times, legal writers must keep in mind what and before whom they argue.

On the topic of effective brief writing, Kaye advised legal writers to avoid “irrelevant fact recitations . . . and ‘kitchen sink’ legal argument”[29]—that is, reciting each and every possible argument. “You get no extra points” for doing so, she said, “and your best arguments may disappear.”[30] Good, focused brief writing “condition[s] the reader to feel that justice is on your side” and includes only those facts that “advance the legal argument you plan to make.”[31] Kaye’s advice frequently centered on appellate briefing, but her lessons are universal. No matter the context, if lawyers don’t know their “objectives, and the major points leading to them,”[32] how can they expect to persuade their readers of anything beyond the profession’s need for remedial writing courses?

A piece of legal writing should take shape in view of what it aims to achieve and with due regard for its audience. The advocate before a court, for example, “can safely assume that all judges have a lot of briefs to read,” and should therefore aim to compose a “clear, concise, cogent presentation of the pertinent facts and contentions.”[33] That cogent presentation is also a matter of structure. As Kaye said, “I never resent being told what the brief writer plans to say . . . and finally being gently reminded of what the writer has established.”[34]

But that’s just step one. Kaye advised advocates to take note of the forum for which they write; for example, “[a]n argument resting solely on ‘fairness’ . . . cannot carry the day” in a court of law with “no ‘interest of justice’ jurisdiction.”[35] And, finally, a piece of legal writing must account for the constraints and pressures on its audience—especially an audience like Chief Judge Kaye’s Court of Appeals. An appellate opinion “resolves a controversy between litigants to be sure, but it also purports to lay down a rule, establish a principle, give guidance to others in similar circumstances.”[36] An appellate advocate’s brief may provide a resolution to the instant case that a judge “can follow easily and have confidence in,”[37] but Kaye recognized that it will not win the day if the rule of law it proposes is not “stable, sensible, and predictable . . . [and] equal to the demands of a changing, maturing, progressing society.”[38]

Or, at least, those demands as the audience sees them.

Think again . . . and again

An effective brief is fully thought through before a word is set to paper.”[39]

To avoid destruction by earthquakes, houses built near geologic fault lines must be sturdy from the foundation up. Kaye believed that a piece of legal writing, too, must be built on solid foundations, lest it crumble amid another seismic event—an experienced lawyer’s close reading. For the legal writer, words put to the page should follow, not precede, a full understanding of the propositions to which they are meant to give effect. In Kaye’s view, words are “how I clothe my thoughts.”[40] Without a clear initial view of the thoughts that words are meant to clothe, how can legal writers ever be sure that their diction best fits the occasion of writing?

Legal writing, unlike some other written forms, is intensely goal oriented. Through it, the lawyer tries to effect a specific result: promoting justice,[41] extolling the virtues of court reform,[42] or winning a case. Without understanding what they seek to accomplish, legal writers cannot know how best to accomplish it. Kaye thought it was better to confront this problem early on, before uncapping her pen. Otherwise, what hope does the legal writer have to “hold [a judge’s] attention . . . establish credibility, win confidence, and ultimately persuade that judge”[43] that her conclusion is the correct one?

Keep it short, keep it clear, and kill your darlings

“A brief is a private oral argument, your time alone with the judge.”[44]

Reading is a solitary activity. Particularly in the law, however, it is a conversation between writer and recipient—whether advocate and judge or petitioner and respondent. Kaye’s advice therefore directs legal writers to ask themselves what their writing would look like if they were standing before its intended reader and making their case in person. Would they use “humor,” “sarcasm,” or “wild rhetoric”?[45] Likely not.[46] In person, they would likely be “clear and communicative,” as their “[w]riting should be.”[47]

Kaye knew that in addition to style, “[b]revity and clarity are also essential ingredients to strong writing.”[48] Generally, and especially in the lives of busy lawyers, “as the length of writings grows, the number of people who actually read them likely dwindles.”[49] A clear, cohesive brief, Kaye said, “will rivet my attention, tend me to the writer’s position, and linger in my mind.”[50] Recalling her days as a journalist, Kaye pointed to clarity done right: “Incomprehensible though the news may sometimes be, you don’t see a lot of semicolons and Latin on our front pages.”[51] Indeed, Kaye’s own “front pages”—the first few sentences of her opinions—briefly and clearly “answer[ed] the question that has beset readers for generations: What is going on here?”[52]

Clarity also means cutting fat.[53] No matter how sweetly a favorite sentence sings, the legal writer should not be afraid to excise it. After all, according to Kaye, styles “come and go, and therein lies a danger in reaching for immortal phrases.”[54] How can the legal writer avoid this pitfall? Put a draft “aside for a day or two”—it’ll help “to insure against those literary flights that shouldn’t survive the blue pencil.”[55] Yet Kaye reserved a role for style in legal writing: “[A]ppellate judges must struggle to find the elusive phrase, the expression that will capture and fix the principle that controls the case. To make a rule and make it memorable,” she said, “occurs only at the intersection of law and literature.”[56]

Sweat the small stuff

“Why risk losing a judge’s confidence, or patience, on account of mechanical matters that are wholly within your control?”[57]

Courts create and enforce generally applicable legal rules, but they also have rules of their own.[58] These rules are exacting. The legal writer may, for example, confront a requirement that each page number in an appendix must be “preceded by the letter A,”[59] or that each heading in an argument section must be “distinctively printed.”[60] These rules warrant strict adherence. Judges may not notice if a submission belongs in a museum of modern design, but “they surely do notice one that is sloppy.”[61] With all the time required to draft a legal document, Kaye reasoned, “you might as well spend the minimal extra time required to do it right.”[62]

The demand for perfection extends beyond the brief writer. Kaye also had advice for other judges, who she said must pay scrupulous attention to every word and piece of punctuation in their opinions lest a “careless comma, a stray phrase, a fanciful footnote . . . come back to haunt in the cases and years ahead.”[63] Further, no legal writer, whether student or chief judge, “can afford to fudge the facts.”[64] Doing so is “suicidal” if it offers the writer’s opponent unearned opportunities.[65] And it’s downright homicidal if it foists false conclusions on “appellate judges . . . [who] shape the law and sometimes even make” it.[66]

Like those judges, Judith Kaye changed the law. But, as she herself wrote about Chief Judge (and later Justice) Benjamin N. Cardozo, Chief Judge Kaye also “changed the way many thought about the law.”[67] The lasting appeal of her writing makes it clear she still does. And if it’s true of a judge’s work that “what is good in it endures,”[68] she will for a long time to come.

Gerald Lebovits ([email protected]), an acting Supreme Court justice in Manhattan, is an adjunct at Columbia, Fordham, and NYU law schools. He thanks Matthew Goldstein (Columbia Law School), his judicial fellow, for his research.

This is Judge Lebovits’s final column. He has served as the Journal’s Legal Writer for 20 years.

[1]. Though her middle name was Ann, Kaye—née Smith—published with the initial S.

[2]. Governor Cuomo’s confidence in Kaye was so complete that when he declined President Clinton’s overtures to appoint him to the Supreme Court, he recommended Kaye in his place. See Jon Lentz, Setting a Precedent: A Q&A with Judith Kaye, New York Nonprofit Media (Jan. 6, 2015), https://nynmedia.com/articles/personality/interviews-and-profiles/setting-a-precedent-a-q-and-a-with-judith-kaye.html (“And did you hear that when he withdrew, he told them to call me?”).

[3]. See generally Sam Roberts, Judith S. Kaye, First Woman to Serve as New York’s Chief Judge, Dies at 77, N.Y. Times (Jan. 7, 2016), https://www.nytimes.com/2016/01/08/nyregion/judith-s-kaye-first-woman-to-serve-as-new-yorks-chief-judge-dies-at-77.html.

[4]. See Hernandez v Robles, 7 N.Y.3d 338 (2006) (Kaye, Ch. J., dissenting) (characterizing as a “misstep” the Court’s decision to uphold New York’s prohibition on gay marriage just seven years before the Supreme Court, in United States v. Windsor, 570 U.S. 744 (2013), held a federal heterosexual-only definition of marriage unconstitutional as an equal-protection violation).

[5]. See id.; Janet DiFiore, A Tribute to Chief Judge Judith S. Kaye, 81 Brook. L. Rev. 1379, 1380 (2016) (listing “elegantly written, well-reasoned opinions” in “so many . . . critical areas”).

[6]. The Associated Press, Stephen R. Kaye, 75, Litigation Lawyer, Dies, N.Y. Times (Nov. 3, 2006), https://www.nytimes.com/2006/11/03/nyregion/03kaye.html.

[7]. Kaye Rules Out Supreme Court Post, Washington Post (Apr. 8, 1993), https://www.washingtonpost.com/archive/politics/1993/04/09/kaye-rules-out-supreme-court-post/78e6f30f-4f72-4800-abe8-7906d24d1cbc/.

[8]. Id.

[9]. Judith S. Kaye, Problem-Solving Courts: Keynote Address, 29 Fordham Urb. L. J. 1925, 1926 (2002).

[10]. The journals in which she published range from the New York Law School Law Review, see Judith S. Kaye, Juvenile Justice Reform: Now is the Moment, 56 N.Y.L. Sch. L. Rev. 1300 (2011–2012), to the Albany Law Review, see, e.g., Kaye, infra note 43. Her work is found in journals and reviews upstate, downstate, and everywhere in between.

[11]. Judith S. Kaye, Reflections on Opportunity in Life and Law, 81 Brook. L. Rev. 1383, 1384 (2016).

[12]. Steven C. Krane, Judith Smith Kaye, Historical Society of the New York Courts (2007), https://history.nycourts.gov/biography/judith-smith-kaye/.

[13]. Id.

[14]. Judith S. Kaye, James P. White Lecture on Legal Education: A Chief Judge’s After-Life: Reflections on Educating Lawyers Today, 45 Ind. L. Rev. 291, 300 (2012) [hereinafter Educating Lawyers Today].

[15]. See, e.g., Judith S. Kaye, Dual Constitutionalism in Practice and Principle, 61 St. John’s L. Rev. 399 (1987) (arguing that state constitutional jurisprudence need not parallel federal courts’ interpretations of the federal Constitution); Judith S. Kaye, Rethinking Traditional Approaches, 62 Alb. L. Rev. 1491, 1494-96 (1999) (explaining New York’s improvements to its jury system during Chief Judge Kaye’s tenure).

[16]. See, e.g., Judith S. Kaye, Women Lawyers in Big Firms: A Study in Progress Toward Gender Equality, 57 Fordham L. Rev. 111 (1988); Judith S. Kaye & Anne C. Reddy, The Progress of Women Lawyers at Big Firms: Steadied or Simply Studied?, 76 Fordham L. Rev. 1941 (2008) (revisiting and revising Kaye’s earlier work in light of new literature and statistics).

[17]. See, e.g., Kaye, Educating Lawyers Today, supra note 14; Judith S. Kaye, One Judge’s View of Academic Law Review Writing, 39 J. Legal Educ. 313 (1989) [hereinafter Law Review Writing].

[18]. In her foreword for the 2002 Tanbook, Kaye “applaud[ed]” the edition’s “decisive step toward clearer, cleaner, more readable decisions, unencumbered by needless, distracting material.” Gerald Lebovits, New Edition of State’s “Tanbook” Implements Extensive Revisions in Quest for Greater Clarity, 74 N.Y. St. B.J. 8, 8 (Mar.-Apr. 2002) (quoting New York Law Reports Style Manual Foreword at iii (2012)). During Kaye’s tenure, and “with [her] enthusiastic support . . . the Tanbook began its evolution from an in-house style sheet to” a comprehensive citation and style guide. William J. Hooks, The Tanbook: A Guide and a Resource, 90 N.Y. St. B.J. 62, 62 (Oct. 2018). (The current edition of the Tanbook can be found at http://www.nycourts.gov/reporter/style-manual/2017/2017-SM.htm.)

[19]. See Judith S. Kaye, Perspective, A Brief for Gender-Neutral Brief-Writing, N.Y.L.J., Mar. 21, 1991, at 2, col. 3 (“[G]ender-neutral writing is not only a good habit but also an easy one to acquire and internalize.”); Judith S. Kaye, Effective Brief Writing, New York Appellate Practice 625, 625 (N.Y. St. B. Ass’n 2013), https://nysba.org/NYSBA/Coursebooks/Fall%202013%20CLE%20Coursebooks/F2013NYAppellateMelvilleRochesterAlbany/F2013MelvRochAlbany.NYAppellate.Coursebook.pdf [hereinafter Brief Writing] (“‘Gendered’ writing . . . [is] so unnecessary.”). Because of Chief Judge Kaye, New York courts strongly encourage gender-neutral language in judicial opinions. See N.Y. St. Jud. Cttee. on Women in the Courts, Fair Speech: Gender Neutral Language in the Courts (2d ed., N.Y. St. Unified Ct. Sys. 1997). The Legal Writer has long championed the Chief Judge as America’s most important advocate for gender-neutral language in the law. See Gerald Lebovits, He Said—She Said: Gender-Neutral Writing, 74 N.Y. St. B.J. 64, 64 (Feb. 2002);

[20]. See, e.g., Judith S. Kaye, Judges as Wordsmiths, 69 N.Y. St. B.J. 10 (Nov. 1997) [hereinafter Wordsmiths].

[21]. Susan N. Herman, Portrait of a Judge: Judith S. Kaye, Dichotomies, and State Constitutional Law, 75 Alb. L. Rev. 1977, 1984 (2011).

[22]. Kaye, Educating Lawyers Today, supra note 14, at 300.

[23]. See id.

[24]. See Kaye, Wordsmiths, supra note 20, at 10.

[25]. Jeanne Sager, Judge Kaye’s Judicial Legacy Is Assured, Sullivan County Democrat (Jan. 22, 2010), https://www.scdemocratonline.com/news/002February/17/kaye.htm.

[26]. Kaye, Educating Lawyers Today, supra note 14, at 300.

[27]. Kaye, Wordsmiths, supra note 20, at 10.

[28]. Kaye, Law Review Writing, supra note 17, at 321 (“As Judge Hand observed, judges ‘furnish the momentum, [academics] the direction; but each is necessary to the other. . . .’”).

[29]. Kaye, Brief Writing, supra note 19, at 625.

[30]. Id. at 626.

[31]. Id. at 627.

[32]. Id.

[33]. Id. at 626.

[34]. Id. at 627.

[35]. Id. at 626.

[36]. Kaye, Wordsmiths, supra note 20, at 10.

[37]. Kaye, Brief Writing, supra note 19, at 627.

[38]. Judith S. Kaye, These Are the Days: Lawyering Then and Now, 82 N.Y. St. B.J. 28, 28 (Jul./Aug. 2010) [hereinafter These Are the Days].

[39]. Kaye, Brief Writing, supra note 19, at 627.

[40]. Kaye, Wordsmiths, supra note 20, at 10.

[41]. See Kaye, These Are the Days, supra note 38, at 30.

[42]. See generally Judith S. Kaye, Refinement or Reinvention, the State of Reform in New York: The Courts, 69 Alb. L. Rev. 831 (2006).

[43]. Kaye, Brief Writing, supra note 19, at 625.

[44]. Id.

[45]. Id. at 626.

[46]. Kaye “could be howlingly funny,” but she never made jokes during oral argument or at the expense of others, behavior she “would likely call . . . aggravated vanity in the first degree.” Albert M. Rosenblatt, Judith Kaye: Beyond Scholarship, to the World of Style and Mirth, 92 N.Y.U. L. Rev. 93, 95 (2017).

[47]. Kaye, Wordsmiths, supra note 20, at 10.

[48]. Kaye, Educating Lawyers Today, supra note 14, at 300.

[49]. Kaye, Wordsmiths, supra note 20, at 11.

[50]. Bryan A. Garner, Judges on Briefing: A National Survey, 8 Scribes J. Leg. Writing 1, 12 (2001-2002).

[51]. Kaye, Educating Lawyers Today, supra note 14, at 300.

[52]. Rosenblatt, supra note 46, at 93. Rosenblatt, id. at 94, notes that in one of her earliest cases, Kaye simply and clearly set out the rule in her first sentence: “A stipulation of a settlement made by counsel in open court may bind his clients even where it exceeds his actual authority.” Hallock v. State, 64 N.Y.2d 224, 228 (1984).

[53]. Kaye furnished a lighthearted example of this principle in recounting her appearance at oral argument before the Second Circuit in 1975. Before she could get out even six words, she was interrupted from the bench: “[I]t will not be necessary to hear further argument. We have decided to affirm.” In retrospect, Kaye wrote, “I have come to believe that this was my best oral argument ever, brief and to the point: ‘May it please the Court. Thank you, Your Honor.’” Judith S. Kaye, The Best Oral Argument I (N)ever Made, 7 J. App. Prac. & Process 191, 192 (2005).

[54]. Kaye, Wordsmiths, supra note 20, at 11.

[55]. Id.

[56]. Judith S. Kaye, Review: Cardozo: A Law Classic, 112 Harv. L. Rev. 1026, 1045 (1999) [hereinafter Cardozo]. Kaye’s colleagues also recognized her idiosyncratic writing style—for example, her the use of the dash as a “stylish substitute for the comma.” Rosenblatt, supra note 46, at 94.

[57]. Kaye, Brief Writing, supra note 19, at 625.

[58]. See, e.g., CPLR 5528–5529 (prescribing formal rules for appellate briefs in New York courts).

[59]. Id. R. 5529(b).

[60]. Id. R. 5528(a)(4).

[61]. Kaye, Brief Writing, supra note 19, at 625.

[62]. Id.

[63]. Kaye, Wordsmiths, supra note 20, at 10.

[64]. Id.

[65]. Kaye, Brief Writing, supra note 19, at 627.

[66]. Judith S. Kaye, The Human Dimension in Appellate Judging: A Brief Reflection on a Timeless Concern, 73 Cornell L. Rev. 1004, 1013 (1988).

[67]. Kaye, Cardozo, supra note 56, at 1038.

[68]. Id. at 1042.

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