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    Wisconsin Lawyer
    January 01, 2017

    Hamilton’s Legal Writing Lessons

    Soldier, politician, lawyer, and cabinet member Alexander Hamilton was also a writer, and today’s lawyers can learn much from his approach to wordsmithing.

    Stephanie L. Melnick

    Alexander Hamilton's likeness on U.S. currency

    “Hamilton,” a musical biography about founding father Alexander Hamilton, starring African American and Latino actors rapping about American history, is a critical and pop culture phenomenon.  It won 11 Tony awards, a Pulitzer Prize, a Grammy, a Kennedy Prize, and a George Washington Book Prize. The show is not only critically acclaimed; tickets for “Hamilton” on Broadway are sold out for months (and selling on the secondary market for thousands of dollars), and the Chicago production is following suit. The New York Times reviewer, Ben Brantley, validated the hype: “Yes, it really is that good.”1

    Lin-Manuel Miranda, “Hamilton”’s creator, admired Hamilton – an orphaned immigrant who rose to political power on the strength of his rhetoric and the force of his will.2 “The ten-dollar founding father without a father/Got a lot farther by working a lot harder/By being a lot smarter/By being a self-starter.”3

    Miranda compares Hamilton to rap artists, poets in their own right. “Just the hustle and ambition it took to get him off the island – this is a guy who wrote his way out of his circumstances from the get­go. That is part and parcel with the hip­hop narrative: writing your way out of your circumstances, writing the future you want to see for yourself.”4

    I Practiced the Law, I Practic’ly Perfected It

    Despite his humble beginnings, Hamilton’s mind and words were firmly based in logic and law.5 Hamilton declined to clerk for a practicing attorney,6 taught himself the law using a friend’s law library, and passed the bar exam after studying the law for six months.7 In Hamilton’s study “outline” – a 177-page manual titled Practical Proceedings in the Supreme Court of New York – Hamilton quipped that courts had “some faint Idea that end of Suits at Law is to Investigate the Merits of the Cause, and not to entangle in the Nets of technical Terms.”8

    Hamilton was a talented and a prolific writer, drafting powerful and important political works – including 51 of the 85 Federalist Papers – while managing a legal practice.9 According to Ron Chernow, who wrote the biography Alexander Hamilton on which the musical is based, “Words were [Hamilton’s] chief weapons….”10

    Hamilton’s ability to boil down an argument to its essence is also evident in his personal letters.

    How Do You Write Like You Need It to Survive?/How Do You Write Ev’ry Second You’re Alive?

    Hamilton’s writings are not only historically significant and politically compelling documents, they also are examples of what legal writing can and, for the most part, should be. 11 By analyzing examples of Hamilton’s work, including several of his Federalist Papers, letters, and publications, certain fundamental principles of legal writing emerge.

    Hamilton’s Lessons in Legal Writing

    Strongest Argument First – Federalist No. 1 (Oct. 27, 1787). Justice Antonin Scalia and Bryan A. Garner, in Making Your Case: The Art of Persuading Judges, encouraged lawyers to start with the strongest argument because “first impressions are indelible.”12 Hamilton dreamed up the Federalist Papers project – “a series of essays, anonymously published,/defending the document to the public” – to garner New Yorkers’ support for the newly drafted Constitution.13

    Stephanie L. MelnickStephanie L. Melnick, U.W. 1994, is a principal in Melnick & Melnick S.C., Mequon, focusing her practice in complex civil litigation, including investment fraud, and business law.

    Hamilton committed to write “The Federalist,” convinced two colleagues (James Madison and John Jay) to help, wrote the majority of the essays, and supervised their publication.14 Hamilton wrote the first essay, The Federalist No. 1, and in the opening sentences highlighted the Constitution’s fundamental importance to the future peaceful existence of a united United States of America.

    “[I]t seems to have been reserved to the people of this country, by their conduct and example, to decide the important question, whether societies of men are really capable or not of establishing good government from reflection and choice, or whether they are forever destined to depend for their political constitutions on accident and force.”15

    Clarity is Paramount – Federalist No. 68 (March 14, 1788). A Georgetown University Law Center professor of legal research and writing, Kristen Konrad Robbins-Tiscione, surveyed federal judges about lawyers’ legal writing skills and found, unsurprisingly, that judges want clear legal analysis in fewer pages.16 Hamilton was clear but not always concise. “Hamilton” recognizes its protagonist’s tendency to ramble: “This financial plan is an outrageous demand,/and it’s too many damn pages for any man to understand.”17

    Still, Hamilton was a gifted writer. Although he did not always value brevity, his goal, to persuade judges, politicians, and the public, required clarity. The Federalist Papers, possibly because of the project’s time constraints (Hamilton, Madison, and Jay wrote 85 essays in seven months18) forced Hamilton to be concise, too.19

    Federalist No. 68 is a great example. Hamilton’s topic was the “mode of electing the President” and he outlined, in order of importance, the why and how of the Constitutional Electoral College system, a system he concluded was if “[n]ot perfect, it is at least excellent.”20 Hamilton identified these reasons, in order, for the Electoral College method of Presidential elections:

    • The “sense of the people” will elect the President by people selected for that purpose at that time.

    • A small group of educated people will be most able to vet candidates.

    • Detached electoral bodies, voting separately in each state, will prevent “tumult and disorder.”

    • Corruption is thwarted because voters are selected separately in each state every four years and no legislator can be an elector.

    • Once elected, the President will be accountable only to the people for reelection.21

    Hamilton then briefly described how the Electoral College system operates and extolled Presidents so elected: “The Process of election affords a moral certainty, that the office of the President will never fall to the lot of any man who is not in an eminent degree endowed with the requisite qualifications.”22 Hamilton analyzed the electoral college system of electing a President – why it was preferable to a popular vote and how it would function – in approximately 1,500 words.23

    Hamilton’s ability to boil down an argument to its essence is also evident in his personal letters. One sentence Hamilton wrote to his wife in a letter to be delivered after his death is a remarkably clear and poignant example, “Adieu best of wives and best of women.”24

    Analyze Legal Authority, Citations Are Not Enough – Federalist No. 81 (June 25, 1788). Accurate citations to applicable legal authority are basic requirements of effective legal writing, and most federal judges think lawyers are doing that well.25 But, lawyers often fail to connect the dots between applicable law and their arguments.26 “[A]dvocates need to tell judges explicitly how the law supports their position, instead of hoping the judge will figure that out for them.”27

    Hamilton analyzed judicial authority (the role of the Supreme Court and lower federal courts) in Federalist No. 81.28 He opened citing the Constitution, article 3, section 1 (“The judicial power of the United States, shall be vested in one Supreme Court…”) and focused on the need for an independent Supreme Court, separate from the legislature.29 Although we take this for granted, Hamilton, a federalist, identified this issue as the remaining question related to the Supreme Court and article 3.30

    The anti-federalists were concerned that an independent Supreme Court would be superior to the legislature because it could construe laws according to the “spirit of the Constitution” and therefore mold “them into whatever shape it may think proper,” without legislative oversight.31

    Hamilton refuted the opposition, relying on the Constitution for support.32 First, he pointed out that the Constitution does not empower courts to apply the “spirit” rather than the language of the Constitution.33 Second, he referred to the essential tenet of the Constitution, separation of powers (“that excellent rule”), and argued that were the Supreme Court part of the legislature it would not be inclined to “temper and moderate” how laws are applied or to find them unconstitutional.34

    Third, again referencing the Constitution, Hamilton highlighted that the legislature cannot overrule a Supreme Court decision; instead, it can “prescribe a new rule for future cases.”35 Hamilton cited and referenced the Constitution repeatedly and each time separately applied its application to his reasoning.

    A Snarky Tone Undercuts Legal Argument – Letter Concerning John Adams (Oct. 24, 1800). Striking the right tone in legal writing can be dicey and varies by type of document and audience. Defining the proper tone – direct but not abrasive, fair but not deferential, convincing but not disparaging – can present a minefield for the unwary.

    Hamilton’s public and published feud with John Adams, then President of the United States, is a cautionary tale. After years of holding his tongue and his pen, Hamilton wrote a “missive indictment” of President Adams, who like Hamilton, was a member of the Federalist party.36 “Adams fires Hamilton/Privately calls him ‘creole bastard’ in his taunts/… Hamilton publishes his response.”37

    Hamilton intended for his letter to be privately circulated among Federalist party leaders.38 But, the opposing party (Republican) obtained the letter and leaked excerpts to newspapers, forcing Hamilton to publish the letter in its entirety and under his own name.39 It is conceivable that ultimately, Hamilton’s take-down of President Adams actually hurt Hamilton more.40 His tone, or anything resembling his tone, is one to be avoided:

    “[President Adams] has certain fixed points of character which tend naturally to the detriment of any cause of which he is the chief, of any Administration of which he is the head; that by his ill humors and jealousies he has already divided and distracted the supporters of the Government; that he has furnished deadly weapons to its enemies by unfounded accusations … that he has made great progress in undermining the ground which was gained for the government by his predecessor, and that there is real cause to apprehend, it might totter, if not fall, under his future auspices.”41

    Respond to Counter Arguments But Don’t Enhance Them – Opinion on Constitutionality of National Bank (Feb. 23, 1791). You read opposing counsel’s brief and the arguments are convoluted and nonsensical, arranged in a strange order, and offer scant analysis. You gather the cases and statutes supporting your client’s position and start preparing your response. But as you write you find that you are clarifying and improving opposing counsel’s arguments as part of responding to them. You are making order out of the chaos. Don’t.

    Instead, follow Hamilton’s lead. Hamilton and Jefferson strongly disagreed about the constitutionality of a national bank, specifically the limits of the Constitution’s necessary-and-proper clause.42 Hamilton acknowledged Jefferson’s argument but did not explain or expound on it.

    “To understand the word [necessary] as the Secretary of State [Jefferson] does, would be to depart from its obvious & popular sense, and to give it a restrictive operation; an idea never before entertained. It would be to give it the same force as if the word absolutely or indispensably had been prefixed to it.”43 President Washington sided with Hamilton and signed the bank bill.44

    Elegant Legal Writing – Federalist Nos. 15 (Dec. 1, 1787), 22 (Dec. 14, 1787), and 78 (May 28, 1788). Legal writing that is clear, concise, and well organized, strikes a proper tone, and addresses (without improving) opposing arguments is effective. But, some legal writing is a cut above, with an aesthetic appeal that raises the bar for all of us.45 Hamilton’s volume of work includes many examples of great legal writing, made more impressive considering the quantity he wrote, when he was writing, and the tools available to him.   

    A universal definition of what constitutes elegant legal writing is elusive. Artistic appeal, even in writing, is more know-it-when-you-see-it than a sum of specific parts. That said, examples of Hamilton’s elegant legal writing abound, including the following:

    “Why has government been instituted at all? Because the passions of men will not conform to the dictates of reason and justice, without constraint.” Federalist No. 15.46

    ”Laws are a dead letter without courts to expound and define their true meaning and operation.” Federalist No. 22.47

    “The Judiciary … has no influence over either the sword or the purse; no direction either of the strength or of the wealth of the society, and can take no active resolution whatever. It may truly be said to have neither FORCE nor WILL, but merely judgment….” Federalist No. 78.48

    I Wrote My Way Out of Hell/I Wrote My Way to Revolution

    Hamilton rose from forgotten founding father to literal and figurative rock star. 49 His face on the $10 bill was saved from replacement by “Hamilton” fans everywhere.50 Huge numbers are now visiting Hamilton-related historical sites, including his home in Harlem (up 70 percent in 2015), his burial site in Lower Manhattan, and Hamilton Park in Weehawken, New Jersey (near the dueling grounds where he was shot).51


    True to the rap narrative, Hamilton wrote his way into the history books and Miranda is making the history books come alive. Hamilton’s words not only teach us about him and our country’s history but also inspire our commitment to good, even great, legal writing.

    Meet Our Contributors

    What is the most memorable trip you ever took?

    Stephanie L. MelnickI studied abroad in Florence, Italy, during my junior year in college. In doing so, I traveled far outside my comfort zone – meeting new people, studying art and art history, learning a new language, and tasting different foods. Somehow, I ultimately managed to blend in; so much so that I was asked for directions routinely (even by Italians who thought I was a local).

    My experience in Florence was not just one memorable trip. While studying abroad, I traveled frequently during the semester and for a couple months thereafter. I visited cities in Italy (including Rome, Capri, Venice, Pompeii, Amalfi, Siena, Assisi, and Naples) as well as Berlin (just after the Berlin Wall fell), Jerusalem, Paris, Munich, Amsterdam, and Salzburg (including the Sound of Music tour).

    But, my time abroad was more than the sum of who I met, what I ate and learned, and where I visited. Meeting people living outside the United States, when I was just 20 years old, fostered my curiosity about and empathy for others’ insights, opinions, and challenges. My unforgettable semester abroad inspired a desire to travel not just abroad but in the United States and Wisconsin, my home state.

    Stephanie L. Melnick, Melnick & Melnick S.C., Mequon.

    Become a contributor! Are you working on an interesting case? Have a practice tip to share? There are several ways to contribute to Wisconsin Lawyer. To discuss a topic idea, contact Managing Editor Karlé Lester at (800) 444-9404, ext. 6127, or email Check out our writing and submission guidelines.


    1 Ben Brantley, Review: ‘Hamilton,’ Young Rebels Changing History and Theater, N.Y. Times, Aug. 6, 2015.

    2 Erik Piepenburg, He’s Taking the ‘Hood to the 1700’s, N.Y. Times, Jan. 6, 2012.

    3 Alexander Hamilton, on Hamilton (from the Broadway musical “Hamilton”). Words and music by Lin-Manuel Miranda. © 2015 5000 Broadway Music (ASCAP). All rights administered by WB Music Corp. All rights reserved. Used by permission of Alfred Publishing, LLC.

    4 Rob Weinertkendt, Rapping a Revolution, N.Y. Times, Feb. 5, 2015.

    5 Non-Stop (from the Broadway musical “Hamilton”). Words and music by Lin-Manuel Miranda. © 2015 5000 Broadway Music (ASCAP). All rights administered by WB Music Corp. All rights reserved. Used by permission of Alfred Publishing, LLC (hereinafter Miranda).

    6 The usual three-year requirement was waived for Revolutionary War soldiers who began their legal studies pre-war. Ron Chernow, Alexander Hamilton 168 (New York, NY: The Penguin Press, 2015).

    7 Id.

    8 Alexander Hamilton, Practical Proceedings in the Supreme Court of the State of New York 49 (New York, NY: American Lawyer Media Inc.- N.Y. L. J. 2004).

    9 Chernow, supra note 6, at 248-50.

    10 Id. at 250.

    11 Miranda, supra note 3, Non-Stop.

    12 Antonin Scalia & Bryan Garner, Making Your Case: The Art of Persuading Judges 14 (St. Paul, MN: Thomson/West, 2008).

    13 Chernow, supra note 6, at 246; see also Miranda, supra note 3, Non-Stop.

    14 Chernow, supra note 6, at 246.

    15 Joanne B. Freeman, ed., Alexander Hamilton Writings 171 (New York, NY: Columbia Univ. Press, 1979).

    16 Professor Robbins-Tiscione sent surveys to all sitting federal judges (excluding senior and bankruptcy judges) in 1999. Forty-six percent of them responded, including one Supreme Court justice, 68 circuit judges, and 286 district court judges. Kristen Konrad Robbins-Tiscione, The Inside Scoop: What Federal Judges Really Think about the Way Lawyers Write, 8 Legal Writing 257, 261, 284 (2002).

    17 Cabinet Battle #1 (from the Broadway musical “Hamilton”). Words and music by Lin-Manuel Miranda. © 2015 5000 Broadway Music (ASCAP). All rights administered by WB Music Corp. All rights reserved. Used by permission of Alfred Publishing, LLC.

    18 Chernow, supra note 6, at 248.

    19 Id. at 250.

    20 Freeman, supra note 15, at 362.

    21 Id. at 362-64.

    22 Id. at 364.

    23 Id. at 362-64.

    24 Id. at 1019.

    25 Robbins-Tiscione, supra note 16, at 270.

    26 Id. at 284.

    27 Id.

    28 Freeman, supra note 15, at 438-41.

    29 Id. at 438.

    30 Id.

    31 Id.

    32 Id. at 439-41.

    33 Id. at 439.

    34 Id. at 439-40.

    35 Id. at 441.

    36 Chernow, supra note 6, at 620-21.

    37 The Adams Administration (from the Broadway musical “Hamilton”). Words and music by Lin-Manuel Miranda. © 2015 5000 Broadway Music (ASCAP). All rights administered by WB Music Corp. All rights reserved. Used by permission of Alfred Publishing, LLC.

    38 Chernow, supra note 6, at 621; Freeman, supra note 15, at 971.

    39 Chernow, supra note 6, at 621-22. Hamilton typically published under a pseudonym, for example “Publius” on the Federalist Papers.

    40 Chernow, supra note 6, at 626.

    41 Freeman, supra note 15, at 970.

    42 Chernow, supra note 6, at 352; U.S. Const. art. I, sec. 8.

    43 Freeman, supra note 15, at 618. When the state of Maryland challenged the constitutionality of the national bank in McCulloch v. Maryland, 17 U.S. 316 (1819), Justice John Marshall referenced Hamilton’s memorandum and adopted his argument. Id. at 341. “[I]f congress could use no means but such as were absolutely indispensable to the existence of a granted power, the government would hardly exist; at least, it would be wholly inadequate to the purposes of its formation.” Id. at 324–25.

    44 Chernow, supra note 6, at 355.

    45 Mark Osbeck, What is “Good Legal Writing” and Why Does It Matter? 4 Drexel L. Rev. 417, 456-57 (2012).

    46 Freeman, supra note 15, at 223.

    47 Id. at 249.

    48 Id. at 421.

    49 Hurricane (from the Broadway musical “Hamilton”). Words and music by Lin-Manuel Miranda. © 2015 5000 Broadway Music (ASCAP). All rights administered by WB Music Corp. All rights reserved. Used by permission of Alfred Publishing, LLC.

    50 Ana Swanson & Abby Ohlheiser, Harriet Tubman to Appear on $20 Bill, while Alexander Hamilton Remains on $10 Bill, Wash. Post, April 20, 2016.

    51 Courtney Sullivan, After the Broadway Show, a Trip to Hamilton’s Grave, N.Y. Times, March 5, 2016.

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