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Authors: Denise Kiernan

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Hardworking, experienced, and a fashioner of fine footwear, Roger Sherman was a man who knew how to compromise—a skill that not only saved the Constitutional Convention but also gave the United States one of the key elements of its government, then and now.

Sherman is the only founder to sign the four most important documents in the early history of the United States: the Articles of Association, the Declaration of Independence, the Articles of Confederation, and the Constitution. But he was no pampered planter’s son sent off to England to study law and buy fancy wigs. No, Sherman was the son of a working farmer and cobbler—one of a handful of signers, including Hamilton and Franklin, who hailed from humble beginnings. He spent most of his youth in what is now Stoughton, Massachusetts. Money was scarce, but the house had plenty of books, and Sherman was a voracious reader. One popular tale—the truth of
which pales in comparison to its charm—says that Sherman slaved away making shoes with a book propped open on his work bench.

After his father’s death, Sherman headed to New Milford to join one of his brothers, and legend has it that he traveled the more than 150 miles by foot while toting all the tools of his trade. (One can only assume he was wearing comfortable shoes!) Upon arriving in Connecticut, Sherman found work surveying property boundaries. He also opened a store with his brother and found time to publish his very own almanac. In 1749, his childhood sweetheart, Elizabeth Hartwell, moved to Connecticut to marry him.

When one of his neighbors needed help with a legal dispute, Sherman lent a hand, and a local lawyer encouraged him to enter the profession. So the shoemaker passed the bar, and yet another skill was added to his growing resume. Over the years, Sherman worked as a town selectman, justice of the peace, county judge, and state senator. He held some form of public office his entire adult life and was often dependent upon the jobs for his income.

In 1760, Elizabeth died, leaving Sherman with seven children to look after. He moved to Chapel Street in New Haven and opened a bookstore near Yale, an institution he would serve in various roles over the years (the university would later grant him an honorary degree). He also remarried, to Rebecca Prescott, and added another eight children to the Sherman clan.

A moderate patriot who favored nonviolence, Sherman attended both the first and second Continental Congresses, from 1774 to 1781, as well as the Congress of the Confederation, from 1783 to 1784—all while making time to serve as a judge back home. He even held the post of mayor in New Haven. In Congress, Sherman was well respected from the get-go, garnering praise from even the most hard-to-please delegates. Notoriously prickly John Adams considered Sherman a friend and described him as “honest as an angel and as firm in the Cause of American Independence as Mount Atlas.” Thomas Jefferson described him as someone who “never said a foolish thing in his life.”

In Congress, Sherman contributed to committees on finance (preferring higher taxes to overprinting paper money) and on military affairs. He served on the Committee of Five that drafted the Declaration of Independence, working alongside primary penman Thomas Jefferson as well as Benjamin Franklin, John Adams, and Robert R. Livingston. He also helped draft the Articles of Confederation.

By the time of the Constitutional Convention, Sherman wasn’t quite ready to abandon the Articles of Confederation—he just wanted to make a few tweaks, and, more important, he wanted a legislature with the power to enforce the laws. At the convention, he spoke at least 138 times in a New England accent that was, for many delegates, incomprehensible; Sherman was a Connecticut Yankee in a well-bred and well-born court.

In his journals, Georgia delegate William Pierce observed that Sherman’s manner might be peculiar, but there was no doubting the man’s ability: “Mr. Sherman exhibits the oddest shaped character I ever remember to have met with. He is awkward, unmeaning, and unaccountably strange in his manner. But in his train of thinking there is something regular, deep and comprehensive; yet the oddity of his address, the vulgarisms that accompany his public speaking, and that strange New England cant which runs through his public as well as his private speaking make everything that is connected with him grotesque and laughable:—and yet he deserves infinite praise—no Man has a better Heart or a clearer Head. If he cannot embellish he can furnish thoughts that are wise and useful. He is an able politician, and extremely artful in accomplishing any particular object; —it is remarked that he seldom fails.”

Throughout the convention, Sherman was clear about his views. He believed that national government should address defense, foreign treaties, and trade while leaving most other matters to the states. He also opposed long term limits, warning that if politicians stayed in the capital for extended periods, they would start adopting the habits and priorities of other politicians and forget the people they represented. (We’re not sure that having two-year terms for representatives has done anything to address this problem.)

For all his concerns about politicians losing sight of their constituents, Sherman was against allowing every citizen to vote. He placed little faith in the average person to make a well-informed decision, saying, “They want [for] information and are constantly liable to be misled.” Sherman wanted the president to be elected by the legislature; if he bungled the job, the legislature would have the power to remove him.

Sherman made history by breaking the convention’s biggest logjam: the problem of representation. As discussed in the introduction, the convention was divided between large states favoring the Virginia Plan (which offered proportional representation based on population) and small states favoring the New Jersey Plan (which allowed for one vote per state, regardless of size). Sherman’s “Eureka!” moment became known as the Great Compromise: there would be two houses, one in which representation was based on population, and the other would be fixed, providing equal representation for every state no matter its size. The deal stuck and the tenor of the Convention changed dramatically, allowing the delegates to move forward together.

After signing, Sherman wrote numerous articles supporting the Constitution for newspapers back home in Connecticut. And this hard-working Puritan didn’t stop once ratification was achieved, despite his advancing age (the only signer older than Sherman was Benjamin Franklin). He went on to be a member of the House of Representatives in the first Congress and then worked as a senator, therefore serving in both chambers of the bicameral legislature whose existence he helped ensure. Few men could,
ahem
, fill his shoes.

Fans of Sherman could argue that the cobbler-judge-surveyor-writer-politician should be remembered as a “co-father” of the Constitution, along with Madison, if for no other reason than that the convention might have imploded without him. His famous descendants include editorial guru Maxwell Perkins and actor Perry King (best known for his role on the 1980s television series
Rip Tide
). Sherman was buried at New Haven Green, but his grave was later moved (as has often occurred with the remains of the signers) to New Haven’s Grove Street Cemetery.

IV. New York

The Signer Who Died in a Duel

BORN
: January 11, 1755

DIED
: July 12, 1804

AGE AT SIGNING
: 32

PROFESSION
: Lawyer

BURIED
: Trinity Churchyard, New York

Slight in size but big on brains, the prickly and persevering “Little Lion” is one of the most impressive and controversial framers of the Constitution. His list of enemies was nearly as long as his list of accomplishments, but the latter has certainly stood the test of time, establishing Alexander Hamilton as a major architectural force in the birth of the U.S. government.

Most of his fellow signers hailed from privileged backgrounds. Hamilton, however, was born out of wedlock to a French mother and a Scottish father in the British West Indies. His father split, his mother died, and by age thirteen Hamilton found himself alone in the world. But the boy was sharp. He apprenticed to a merchant in town, but his intellect and ambition craved more. When a great hurricane struck the islands in 1772, he wrote a letter describing it, which
ended up printed in the local newspaper. Hamilton’s writing was impressive, prompting Nicholas Cruger, one of his bosses, and local Presbyterian minister Hugh Knox to raise funds to send him to America. They packed him off with a bit of money and several letters of introduction. One was addressed to fellow Presbyterian William Livingston of New Jersey, who took in Hamilton for a spell, arranged for his education, and later signed the Constitution with him.

From an early age, Hamilton supported the revolutionary cause. When he was just eighteen years old, he made speeches in support of the Boston Tea Party and established his reputation as a pamphleteer. When the war came calling, it was like a siren’s song. He volunteered for the militia and was drafted by the state, with a commission as a captain. He fought in Long Island, White Plains, Trenton, and Princeton, but his most significant assignment came in 1777, when he became one of General George Washington’s aides-de-camp. The two men (separated in age by two decades) became fast friends and developed a relationship akin to father and son. (Not surprising since Washington fathered no children, and Hamilton had been abandoned so young.) Although the trusted confidantes later suffered a falling-out, Washington still trusted Hamilton enough to give him command of a battalion of light infantry in Yorktown. There, the young captain led a famous and tremendously successful nighttime bayonet assault on Redoubt 10, five days before the surrender of General Cornwallis.

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