Letters of a Countryman

“But would not the people be as safe, governed by their representatives assembled in New York or Philadelphia, as by their representatives assembled in Hartford or New Haven?”

Summary Overview

In 1787, the Constitutional Convention completed its work on the US Constitution and began the process of ratification. Each state legislature was approached to discuss and approve the tenets of the document. In Connecticut, delegate Roger Sherman wrote the “Letters of a Countryman,” a series of open letters addressed to the leaders and citizens of his home state to advocate for ratification. In the letter, Sherman—a longtime Connecticut resident, Federalist, and contributor to the Declaration of Independence—addresses the arguments of Anti-Federalists who expressed concern over the Constitution’s creation of a strong federal government and stresses the protections offered the states through federal union.

Defining Moment

In 1787, the United States of America set about the task of finalizing the Constitution, a document that laid the foundation of government for the new nation. Having undergone frequent changes during the Constitutional Convention, the final document was delivered to the states, whose legislatures were to review, debate, and ratify it.

The process of ratification was complicated, however, by the growing division between two main factions. On one side were leaders who believed in a strong centralized government that would focus on matters of national importance, such as international relations and defense. On the other side of the issue were the so-called Anti-Federalists. Most members of the latter camp felt that the United States should be decentralized, with the state governments playing the primary role in leadership. The group also believed that the Constitution should include language that identified the basic rights of all American citizens.

As the Constitution was delivered to each state legislature, both the Federalist and the Anti-Federalist factions launched public relations campaigns. A series of essays and open letters appeared in each state, written by authors using pseudonyms. The Anti-Federalists, including New York governor George Clinton, Pennsylvania legislator James Wilson, and Virginia’s Patrick Henry, wrote and spoke out against ratification. A major argument made in the Anti-Federalist Papers was that a strong centralized government had the potential to introduce domestic tyranny as a replacement for British tyranny. Additionally, the Anti-Federalists argued that the Constitution needed more emphasis on the rights of the citizens.

On the other side of the campaign were the Federalists, who, in response to the Anti-Federalist Papers, issued their own (and arguably better known) Federalist Papers. John Jay, Alexander Hamilton, and James Madison, writing under the pseudonym Publius, published and distributed a number of pamphlets advocating ratification and adoption of the federal style of government.

As the ideological debate took place, Connecticut’s situation added another challenge to the development of the Constitution. Under the Articles of Confederation (which, in 1777, established the state governments), the small state of Connecticut suffered economically—the state’s economy was weighed down heavily by war debts and large sums owed to New York. Sherman, Oliver Ellsworth, and William Samuel Johnson were sent by the state to the Constitutional Convention in the hopes that the new government would be respectful of the small states’ condition. The alternative was a system in which small states would continue to be beholden financially to large states (as Connecticut was to New York and Massachusetts).

As a result of the three delegates’ lobbying efforts, the Connecticut Compromise, as it was known, created a system of proportional representation in Congress, giving small and large states equal legislative footing. Sherman, Ellsworth, and Johnson returned to Connecticut to see the ratifying convention dominated by like-minded Federalists. Connecticut ratified the Constitution in a matter of only days.

Author Biography

Roger Sherman was born on April 19, 1721, in Newton, Massachusetts. Sherman’s father, William, was a farmer and a cobbler who taught him both trades. His childhood education was not of high quality, but his extensive reading strengthened his knowledge. In 1743, Sherman left the greater Boston area following the death of his father (an event that left Sherman’s family poor), relocating his mother and family to New Milford, Connecticut, where his elder brother had moved several years prior. There, Sherman established a small shoe-making business.

Not long after he moved to the area, Sherman assisted a friend in a legal matter. The attorney involved encouraged Sherman to pursue a legal career. Sherman began studying law, but he also remained in business, purchasing a store with his brother. Meanwhile, Sherman became heavily involved in local politics. At the age of twenty-four, he was elected county surveyor, the first of what would be many political posts.

In 1749, Sherman married Elizabeth Hartwell, with whom he had seven children (she died in 1760, and Sherman remarried in 1763). In 1754, he was admitted to the bar, having educated himself on the law. Between 1755 and 1761, Sherman held many political posts, including justice of the peace and county judge. In 1765, he became judge with the county court of appeals while serving as both treasurer and benefactor of Yale College (which gave him an honorary master’s degree thereafter).

In 1766, Sherman became a member of the colonial legislature, serving in the upper house until 1785. During this period, the colonial pursuit of independence from British rule intensified. Sherman was appointed a delegate to the Continental Congress in 1774. Among his accomplishments were membership on the committee dedicated to drafting the Declaration of Independence and his work on the Articles of Confederation. He also remained an active member of Connecticut’s legislature during this period.

Sherman served as a member of the Continental Congress from 1774 until 1781 and again from 1783 until 1784. He continued to be a prominent figure in Connecticut, however, holding the office of judge in the state’s superior court from 1777 to 1779. In 1783, he played a central role in the codification of Connecticut’s laws, and in 1784, he was elected mayor of New Haven.

While mayor, Sherman represented Connecticut at the 1787 Constitutional Convention. With his “Letters of a Countryman” and his presentations to the Connecticut legislature, he helped win ratification of the Constitution. In 1789, Sherman was elected to the US House of Representatives. Two years later, he was elected to the US Senate. He remained a senator until his death on July 23, 1793, in New Haven.

Roger Sherman.

(Library of Congress)

Document Analysis

The first of Sherman’s five letters, which were printed in the New Haven Gazette, reports to the readers that the new federal Constitution was complete and ready for ratification. Ratification entailed making what Sherman calls “important alterations” to the government that was then operating under the Articles of Confederation. Sherman’s letter suggests that the new form of government established in the Constitution would undoubtedly be advantageous to the people of Connecticut and therefore induce them to support ratification. Then again, he acknowledges that most of the provisions of the document might be well received while others might be less agreeable than those of the current government were. His stated hope is that the advantageous provisions would not be gained based on the sacrifice of the positive attributes of the confederate (state-oriented) government already in place.

Sherman recognizes that the risks incurred by ratification naturally and “justly” generate caution among those citizens considering new forms of government. It is typical, he suggests, for the parties considering such changes to focus on what might be sacrificed, however small, rather than what might be gained overall. While he expresses hope that the perceived benefits of the new national government would outweigh the risks in the minds of Connecticut residents, he appreciates their cautious perspective. This type of approach is, in the words of Sherman, a “wise provision in the constitution of man.”

Sherman then addresses one of the specific fears that had arisen regarding the formation of a strong central government. The citizens of large states are concerned about their territories being broken down into smaller states, a notion that, for many, seems akin to accepting “ruin.” Meanwhile, the citizens of small states worry about a loss of power when merging with large states. To illustrate the point, he adds that even a small, ten-square-mile section of land adjacent to (but historically independent of) Connecticut would resist the idea of joining Connecticut, out of fear that such an action would compromise the security of the people living therein. Opponents of joining a larger state would see a loss of security if their leaders, instead of staying within the land, were sent to represent them in the Connecticut legislatures in Hartford or New Haven. Sherman envisions that the people of the hypothetical parcel of land might even resort to violence in order to prevent integration into a larger territory. The people would resist with all of the defiance Scottish leaders demonstrated at a proposed union with Great Britain at the beginning of the eighteenth century. In fact, the small region might resist with the same vigor that the colonies had demonstrated against the British only a few years prior.

Of course, Sherman says of the hypothetical situation, the predicted loss of security from joining Connecticut would be minimal. In fact, stability and security might be enhanced, he suggests. To be sure, there would likely be minor differences in the level of security between the region’s independent status and its status as part of Connecticut. Sherman sees attitudes to the contrary as based on the rhetoric of opponents to ratification, not on matters of fact. If the fears manifest in the hypothetical situation were well founded, every town in the state might have remained independent and without any state government. Instead, the towns of Connecticut united, a decision that Sherman asserts has ultimately served those communities best.

Sherman continues his argument for constitutional ratification by stating that if each city and town in the state retained its independence and did not unite to form a state government, political leadership in the region would be “weak and irregular.” While he acknowledges that each community sacrifices its independence and most of its administrative authority to the state, he sees no negative impacts. Rather, the people’s security, property, and general way of life had never been put at risk when states, large and small, were formed. Taxes remain equitable and not overly burdensome for the people, even in states that formed from the unification of many different towns and cities.

Sherman clearly prefers a small state over a large state, however. He maintains that single towns in smaller states such as Connecticut retain a much larger percentage of their self-governing authority than those that are part of large states, due to the greater proportion of legislative representatives serving the communities. As government grows, so too do the districts (in terms of geography and population) served by legislators. Sherman argues that Connecticut’s state government has reached a point at which its communities retain the ability to govern themselves with regard to local matters while maintaining control over their state legislators. Nevertheless, he asserts that the introduction of a national government need not place this balance between state and local government at risk.

Next, Sherman responds to the Anti-Federalist argument that a large federal government would present a greater danger of becoming a tyrannical and oppressive presence in America than would a confederation of state governments. However, the federal government model was based on the notion that those chosen to represent the people (as was also the case at the state level) were of strong moral character. Therefore, Congress would be composed of exceptional people, a characteristic that meant that the federal government would be of the highest quality.

If the government provided by the Constitution was as good as the state governments, Sherman argues, the federal government is in no more danger of becoming a tyranny than state governments are. In fact, he states, many “great men” have gone to the Connecticut legislature in Hartford and New Haven a few times a year, drafting and issuing new laws and regulations for the benefit of the people. Although they travel great distances to govern on behalf of local residents, the legislators, according to Sherman, remain upright, even from afar. For members of Congress to devolve into supporters of tyranny, they would necessarily veer from the high moral standards and upstanding character expected of state government officials. Sherman sees no evidence that the creation of the federal government would cause such a shift or that the people would allow such a change to occur.

To be sure, under the Constitution, fewer legislators from Connecticut would be sent to the national capital (which was then in New York and later Philadelphia) as would be sent to the state capital. Under the federal government, the geography covered by members of Congress was much larger than that covered by the state government and the number of members of Congress representing the regions was much smaller than the number of representatives at the state level. However, Sherman argues, the people would be just as safe with their legislators traveling to the nation’s capital as they would with their legislators traveling to New Haven or Hartford.

According to Sherman, in numerous historical instances, people have lived in poverty and otherwise unsafe conditions largely because their states were small and unaffiliated. By contrast, finding similar examples of poverty and instability caused by communities that joined to form larger states is difficult, Sherman argues. He cites the example of Scotland joining England at the beginning of the eighteenth century. The Scots did not become poor or overly dependent by joining Great Britain; rather, he claims they were “much more secure, happy and respectable.” By comparing the situation of Connecticut and other small states to the one between Scotland and England, Sherman assures his readers that American unity is nothing to fear, even if it means the country would be far greater in size than each of the states within it.

Sherman’s fourth letter appeals directly to the people, seeking to address the concerns they might have about handing power and authority over to a federal government. Sherman begins the argument by speaking to the concept of a representative form of government, which was not then a new one. He assures his readers that issues regarding the idea of entrusting leadership and governmental authority to a group of designated legislators arose during the drafting of the Constitution. Changing the size of the government is a matter of trust, Sherman suggests: The people need to trust those to whom they hand their sovereignty and must first determine if they can accept the concept philosophically, as they might place their freedom at risk.

However, the democratic model of government was not a new concept to the people, nor was the notion of surrendering freedom to legislative representatives. As Sherman reminds them, the Connecticut General Assembly was already entrusted with “all the powers of society.” Sherman asks the people if any other freedom has yet to be handed to the legislature to protect. The general assembly consists of leaders whom the residents of Connecticut have been deemed worthy, and he notes that the people have taken no issue with their leadership.

Therefore, Sherman asks the people of Connecticut why they might take further issue with putting aside a portion of the freedom they had already given to representatives in the state’s general assembly and reallocating it to the new federal congress. In Sherman’s opinion, placing trust in the hands of Congress, rather the state assembly, is better for the people. If the members of Congress are worthy of the trust of the residents of Connecticut, then there should be no concern about placing political authority in the hands of elected national figures.

Next, Sherman analyzes the differences between the general assembly and Congress. First, he asks his readers what forms the basis of security that the general assembly provides. In Sherman’s estimation, security derives from the fact that the interests of the members of the legislative body are the same as the people they serve.

Then, Sherman focuses on what he considers the two main differences between Congress and the general assembly. First, Congress is much larger than the general assembly because it is, after all, responsible for governing a much larger tract of land than the state government is. Thus, Sherman admits, Connecticut residents’ share of the national government will be considerably smaller than the share they possess at the state level. He refers to his first letter, wherein he cites his preference for smaller states and the considerably greater share of government those entities feature, which, he acknowledges, is significant, demonstrating “all the force as an objection against the powers of Congress.” Then again, the issue was also visited when communities were considering unifying into states, sacrificing their municipal “sovereignty” to form larger state governments.

Sherman also addresses a concern among the people that the six to eight leaders that would be sent to New York are expected to be members of high society, owning great sums of property and feeling little of the burdens other residents of the state experience. Sherman dismisses this notion, saying that there is no evidence the legislators sent to represent the people will somehow detach themselves from the less affluent people they represent. Rather, the legislators will be of the people, paying their own taxes and being careful about further burdening the poor with tax liability.

The trustworthiness of affluent representatives was of greater concern in the past, when the issue of giving up power or authority to any form of government was being debated, Sherman alleges. When the municipalities considered merging to form state governments, for example, they might have used such an argument, particularly when railing against the idea of giving candidates of stature (but perhaps no fiscal discipline) the authority to spend the people’s money outside of the community. Sherman reminds readers that this fear was never realized. Rather, evidence from that period suggested that the legislators sent to Hartford or New Haven to work in state government were careful spenders, mirroring the behavior of any other person: They spent the money necessary to pay debts and deposited whatever sums into a bank to gain interest. There is no difference in this regard, Sherman concludes, between a state legislative body and a church or school district, both of which would only spend what was necessary to survive.

Sherman continues his discussion by stating that, for the most part, the people are the representatives, working through those whom they vote into office. Although not everyone could vote, all pay taxes in some form or another, and these spent by their elected officials; thus, in essence, the people’s votes are used for the purposes of spending the people’s money.

Not all regions levy the same amount of taxes, Sherman adds. In smaller communities, taxes have been levied more “willingly” than at the state level; local tax revenues, he suggests, are more immediately vital to the community governments to fund the development of infrastructure and sustain a growing population. Meanwhile, state governments are less inclined to apply statewide taxes with such vigor, he claims, because these institutions opt to live within their means, taxing the public just enough to pay their annual debts. Sherman further states that the general assembly of Connecticut would never allow itself to spend more than its annual debts required, and he points to the general assembly’s history for examples of its fiscal discipline.

Sherman provides an example of a man who is owed money by the town in which he lives: The man simply needs to apply for a hearing at the annual town meeting. In all likelihood, Sherman claims, the man would succeed in his application. However, if the man filed a similar case at the state level, he would likely find resistance from the legislature or executive agency, which would prefer to retain the money if at all possible. In Sherman’s estimation, the state would attempt to lessen the amount of money owed by as much as half.

As the level of government widens (from local to national), the level of willingness to spend the taxpayers’ money beyond what is expected would decrease proportionally, Sherman maintains. He suggests that the members elected to represent Connecticut in Congress would carry the characteristic of fiscal responsibility to an even greater degree. Sherman adds that the people have likely seen evidence of their respective elected officials’ careful spending habits and that the voters have no reason to believe that Congress would take a different approach. Because many legislators are owners of property or otherwise independent of government when they become leaders, Sherman believes they could therefore be trusted to spend taxpayer money in the same frugal and conservative manner in which they conduct themselves. The skeptical view to the contrary, Sherman suggests, is therefore neither valid nor possible.

Essential Themes

For a number of reasons, Sherman’s five letters to the people and leaders of Connecticut (together dubbed “Letters of a Countryman”) were presented to an already captive audience. Sherman and his fellow delegates to the Constitutional Convention had successfully addressed, through what would later be known as the Connecticut Compromise, a number of issues that placed small states at a perceived disadvantage in comparison to larger states such as New York. The Constitution that was placed before the people of Connecticut for consideration already had a number of provisions that small states would find agreeable.

Then again, the fervent campaigning of the Anti-Federalists in each state led the Constitution’s Federalist framers to generate a response. In letters 1 and 4 of his series, Sherman attempts to address a number of concerns about a perceived loss of state sovereignty and the quality and size of the proposed federal government. Here, Sherman writes not as an agent of the federal government but as a resident of Connecticut. His approach is important, given that he had an understanding of how Connecticut’s unique form of government had developed since the Articles of Confederation and how it would be affected by the introduction of a federal system.

Sherman’s first letter addresses the issue of state sovereignty. He acknowledges that Connecticut’s state government would sacrifice some of its authority to the federal government, but he argues that the sacrifice would not negatively impact the people’s way of life. Sherman also discusses the idea that a federal government would open the door for a return to tyranny. He dismisses the idea, reminding Connecticut residents that they sent to Hartford and New Haven legislative representatives who were of the highest character and who demonstrated the utmost respect for the people they serve. Sherman asserts that there is no reason to believe that the people of Connecticut would send corruptible individuals to New York if they have sent good leaders to the general assembly.

Sherman’s fourth letter explores the differences between the general assembly and Congress. He reiterates that the change in government would be significant, involving a “sacrifice” of certain aspects of state sovereignty. He notes, however, that Congress, in taking up matters of national importance, would demonstrate the same quality of public administration as its state counterparts. Specifically, Sherman argues that congressional representatives would show a strong sense of fiscal discipline reflective of the approaches of small businesses, churches, and financially successful individuals.

Consistent throughout Sherman’s letters is an acknowledgement that the Constitution would bring significant changes to the American style of government. However, these changes were not to be dreaded, he argues, nor were they completely alien in nature. The transition to a federal system would not, in Sherman’s opinion, threaten the rights or interests of the people (or the states in which they live). Ultimately, a vote in favor of ratification would benefit the new country and have few adverse effects.


  • “America’s Founding Fathers: Delegates to the Constitutional Convention.” The Charters of Freedom. US National Archives, 2012. Web. 25 July 2012.
  • “Connecticut Ratifies the Constitution.” American Memory. Lib. of Cong., 13 Oct. 2010. Web. 25 July 2012.
  • Johnston, Hillary. “Sherman, Roger.” Pennsylvania Center for the Book. Pennsylvania State University, 2011. Web. 28 June 2012.
  • “Roger Sherman.” Roger Sherman Society. Roger Sherman Society, n.d. Web. 25 July 2012.

Additional Reading

  • Collier, Christopher. Roger Sherman’s Connecticut: Yankee Politics and the American Revolution. Middletown: Wesleyan UP, 1971. Print.
  • Ketcham, Ralph, ed. The Anti-Federalist Papers and the Constitutional Convention Debates. New York: Signet, 2003. Print.
  • Lynch, Joseph M. Negotiating the Constitution: The Earliest Debates over Original Intent. Ithaca: Cornell UP, 2005. Print.
  • Maier, Pauline. Ratification: The People Debate the Constitution, 1787–1788. New York: Simon, 2011. Print.
  • Stewart, David O. The Summer of 1787: The Men Who Invented the Constitution. New York: Simon, 2007. Print.