Charles Carroll of Carrollton - America's First Entrepreneur
- Craig Rhinehart
- Aug 31
- 18 min read
Updated: 7 days ago
Project Backgrounder
The Remarkable 95-Year Life of America’s Founding-Era Entrepreneur
When Charles Carroll of Carrollton died in 1832 at the age of 95, the United States was almost unrecognizable from the British colony into which he had been born.
He had lived under three British kings. He had watched the colonies rebel, helped create an independent nation, served in its first governments, invested in its growing economy, supported canals and other transportation improvements, and finally helped launch the railroad age. Very few Americans witnessed these chapters of the country’s development. Only one American helped shape all of these chapters of the country’s development.
Most Americans know him for two things. He was the only Catholic signer of the Declaration of Independence, and the last surviving signer.
Most of the Founding Fathers are only remembered for what they wrote, said, or signed in 1776.
Carroll deserves more attention for what he continued to build, back, and help set in motion over the 50+ years that followed.
Project Lens
Charles Carroll of Carrollton - America’s First Entrepreneur examines the life of Charles Carroll of Carrollton (1737–1832) through a broader lens just being the only Catholic signer, and the last surviving signer, of the Declaration of Independence.
He had every reason to stay cautious with a famous name, inherited land, family standing, and enough wealth to drift into an easy life. But Carroll did not live passively from what he inherited.
He was expected to take over a family platform built by his father and grandfather.
Carroll had to learn it, operate it, protect it, and extend it. He had to think in terms of continuity, leverage, and long-term value.
He also had to learn to work through strategy, networks, and persuasion. This was especially true in a world where certain traditional paths were closed to him.
As a Catholic in colonial Maryland, he faced real social discrimination and legal limitations. He had to become skilled at debate, alliances, and influence. Rather than relying only on office or position.
He repeatedly took calculated risks by putting his capital, reputation, family security, and even his own life for larger causes and longer-term outcomes.
Seen through that lens, Charles Carroll begins to look like something more than a patriot and wealthy statesman. He looks surprisingly entrepreneurial.
Part of what drove him was that he always had something to prove. He lived in the shadow of his father and grandfather. He lived in the shadow of his own famous name that he had to share. He lived in the shadow of a great family fortune, and the very large shadow of a society that distrusted and excluded Catholics.
But that pressure became a kind of quiet advantage, or his superpower. He was not bombastic, or fiery, like some of the other founders. He possessed a quiet determination to accomplish what he set out to. I suspect had a bit of an “I’ll show you” chip on his shoulder underneath all that determination.
Carroll was unquestionably a Founding Father with an accomplished public service record. He served in the Continental Congress, spent more than two decades in Maryland government, and became one of Maryland’s first United States senators. But the traditional political biography captures only part of his importance.
Across a 95-year life, Carroll was also a large-scale landowner and estate manager, lender, investor, agricultural operator, participant in iron manufacturing, supporter of banks and educational institutions, advocate for transportation improvements, and ultimately a founder and director of the Baltimore & Ohio Railroad.
The project uses “America’s First Entrepreneur” as an interpretive lens rather than a literal claim of chronological primacy. Its purpose is to examine Carroll as a founding-era entrepreneur: someone who repeatedly combined capital, management, calculated risk, networks, political influence, and investment in systems capable of producing long-term economic value.
Viewed chronologically, his life follows a remarkable progression:
Preparation → Operation → Influence → Patriotism → Stewardship → System-Building → Philanthropy and Legacy
It also provides a bridge between two major periods of American development: the political revolution that created the United States and the transportation and industrial revolution that helped connect and develop it.
Historical Background
Charles Carroll (of Carrollton) was born in Annapolis on September 19, 1737, into one of colonial Maryland’s wealthiest families. That house still stands today. The economic foundation he inherited had been created over several generations.
His grandfather, Charles Carroll “the Settler,” arrived in Maryland from Ireland in 1688 and initially served as Attorney General under the Catholic Calvert proprietorship. Political upheaval following Maryland’s Protestant Revolution sharply reduced Catholic political power. The elder Carroll responded by building influence through commerce, property acquisition, lending, and estate development.
By the early eighteenth century, the Carroll family possessed extensive landholdings and had become one of the most economically powerful Catholic families in Maryland.
Charles Carroll of Annapolis, Carrollton’s father, expanded and consolidated this inheritance. Doughoregan Manor became the family’s principal country estate and the operational center of a large agricultural and property enterprise.
The result was an unusual environment for the younger Charles Carroll. He was born into enormous economic privilege while simultaneously belonging to a religious minority whose members faced substantial restrictions on voting, holding public office, practicing law, and participating fully in Maryland political life.
That contradiction became one of the central forces shaping his life.
1737–1765
Preparation: Enabling a Life That Matters
Carroll’s family prepared him carefully for leadership.
After early schooling in Maryland, he was sent to Europe in 1748. He studied at Jesuit institutions including St. Omer and Louis-le-Grand and later pursued legal studies in France and England.
As a result, he spent a significant portion of his youth and early adulthood overseas. During this time, he and his father exchanged numerous letters.
By the time he returned to Maryland in 1764 or 1765, Carroll possessed an unusually broad education for an American colonist. He understood law, European politics, commerce, classical thought, languages, and Catholic intellectual traditions. He also spoke French and was also thoroughly educated in Latin, Greek and Italian according to reviewed sources.
Yet Maryland’s religious restrictions prevented him from simply converting that education into a conventional political or legal career.
The normal route was blocked. His first important arena therefore became the family enterprise.
1765–1772
Operation: Learning and Running the Family Business
The years immediately following Carroll’s return were formative because they gave him practical experience managing wealth rather than merely inheriting it.
Doughoregan Manor and the wider Carroll property holdings constituted a substantial business organization largely based on tobacco. Their management involved agricultural production, tenants, leases, credit, accounting, land transactions, debt collection, overseas trade, and long-term property planning.
Carroll married Mary “Molly” Darnall in 1768 and began assuming greater responsibility within the family’s economic system.
Carroll recognized the significance of forming alliances. The Darnall family was clearly a crucial family ally. Other extended family members, like Charles Carroll "the Barrister," were significant in new business ventures.
Carroll built a strong and mutually beneficial business network that lasted his entire life. Apart from his family, he notably trusted and did business with a young and ambitious land speculator named George Washington and a visionary family of driven brothers from Bucks County, Pennsylvania, known as the Ellicotts. The Ellicotts had recently moved to the Patapsco River Valley in Maryland, near Carroll's base of operations at Doughoregan Manor.
This was also a period when Maryland’s economy was changing.
Tobacco remained important, but wheat and flour increasingly connected Maryland agriculture with larger Atlantic markets. When the Ellicott brothers established their milling operations on the Patapsco River beginning in 1772, they encouraged surrounding farmers to expand wheat production.
Carroll collaborated with the Ellicotts in four distinct ways and engaged in the agricultural and financial landscape emerging around Ellicott’s Mills.
This local relationship illustrates one of the project’s central themes:
Carroll increasingly understood economic value as the product of interconnected systems:
Goods produced on agricultural land needed markets.
Tobacco was a lower-value commodity, whereas wheat and other grains had higher value when processed.
When the crops were processed (milled), markets became more accessible and offered higher value.
Accessing markets increasingly demanded faster and more reliable transportation (such as better roads and canals).
Transportation required capital.
And capital depended upon financial institutions, credit, and confidence.
This way of thinking would remain visible throughout his life.
1772–1774
Influence: Becoming “First Citizen”
Carroll’s political emergence began not through elected office but through public argument.
In 1772–1773 he entered a major newspaper controversy with Daniel Dulany over Governor Robert Eden’s proclamation concerning government fees.
Writing as “First Citizen,” Carroll argued that government authority had constitutional limits and that executive officials could not impose charges without proper legislative authority.
The dispute made him widely known. It also made him more influential.
His essays demonstrated the legal training, disciplined reasoning, and controlled rhetorical style developed during his European education.
More importantly, they established a method Carroll would repeatedly use throughout his career:
When formal authority was unavailable, he built influence through knowledge, credibility, networks, and persuasion.
The politically restricted Catholic landowner had become one of Maryland’s most important public voices.
1774–1776
Patriotism: Taking Action
As conflict with Britain intensified, Carroll moved rapidly from public commentator to revolutionary leader.
In 1774, Maryland’s revolutionary conventions bypassed, rather than formally repealed, the colonial laws excluding Catholics from office, enabling Charles Carroll to carefully enter public life as a delegate.
He participated in Maryland committees supporting colonial resistance and became associated with figures including Matthew Tilghman, Samuel Chase, William Paca, Thomas Johnson, and other leaders of Maryland’s revolutionary movement.
He was present during the 1774 Peggy Stewart controversy in Annapolis and participated in Maryland’s emerging revolutionary political organizations.
In early 1776, the Continental Congress selected Carroll for its diplomatic mission to Canada alongside Benjamin Franklin, Samuel Chase, and Father John Carroll (his cousin who later became the nation’s first Catholic bishop).
His selection was revealing.
Carroll’s Catholic identity, French fluency, European education, social standing, and political credibility made him particularly suited to dealing with French-speaking Catholics in Quebec.
The mission failed to bring Canada into the American cause, but it moved Carroll decisively into national affairs.
Upon his return, Maryland’s position on independence became critical.
Maryland had earlier directed its Continental Congress delegates against voting for independence. However, on June 28, 1776, under the influence of Carroll and Samuel Chase, the Maryland Convention ultimately lifted those restrictions, permitting its delegation to endorse separation from Britain.
Carroll was then appointed to the Continental Congress. He took his seat on July 18, 1776 in Philadelphia and was almost immediately trusted with serious work.
Writing later of Carroll’s appointment .. John Adams called him “an excellent member .. whose education, manners, and application to business did honor” to what Adams called “the greatest fortune in America.”
The Declaration of Independence
He arrived after Congress had approved independence on July 2 and adopted the Declaration on July 4, 1776.
A number of signatures were still needed and he arrived in time for the formal signing.
On August 2, 1776, he signed: Charles Carroll "of Carrollton"
The geographic designation distinguished him from the many other Charles Carrolls in Maryland.
It also ensured there could be no ambiguity concerning which Charles Carroll had committed himself to independence.
Carroll was the only Roman Catholic among the 56 signers.
For a man possessing one of the largest private fortunes in America, the decision represented substantial personal exposure. If the Revolution failed, his life, property, family fortune, and social standing could all have been endangered.
Under the entrepreneurial framework of this project, the signature represents perhaps Carroll’s greatest calculated risk.
He did not merely advocate independence.
He put his capital, reputation, and identity behind it.
1776–1800
Stewardship: Building Effective Government
After independence, Carroll’s career became less dramatic but arguably more important to the long-term functioning of the new nation.
Carroll served on the committee that drafted Maryland’s 1776 constitution, helping design a government with separate branches, a bicameral legislature, and an elected senate. Maryland’s use of electors to select senators became an important precedent that was = incorporated into the U.S. Constitution eleven years later.
He served in the Maryland Senate beginning in 1777 and became its president in 1783. He also returned periodically to the Continental Congress.
His work focused heavily on the machinery of government: finance, taxation, debt, military supply, property, law, public credit, and institutional stability.
Carroll was not primarily remembered as a great floor orator.
His strength was closer to that of an operator.
He drafted reports, prepared legislation, worked through committees, negotiated institutional problems, and dealt with the complicated financial issues facing Maryland after the Revolution.
He increasingly supported a stronger national government and became associated with the Federalist movement. His deepened relationship with George Washington involved exchanging political intelligence.
When the proposed Constitution reached Maryland, Carroll participated in the process that placed it before a state ratifying convention.
In 1789 he became one of Maryland’s first United States senators.
He served until 1792, when Maryland law required him to choose between continued service in the state legislature and service in the U.S. Senate.
He chose Maryland.
Carroll remained in the Maryland Senate until approximately 1800.
The significance of this period is central to the project.
The Declaration created political independence. Carroll then spent decades working on the less celebrated challenge of making independence function.
Maryland formally honored Carroll’s service by commissioning his monumental State House portrait in 1834 and, in 1903, selecting him as one of the state’s two representatives in the U.S. Capitol’s National Statuary Hall Collection, ensuring that his “useful life and glorious example” would be remembered by future generations.
The Business Portfolio
Carroll never separated his public career completely from his private economic activities.
He remained involved with the management of land, leases, lending, agriculture, investments, and other enterprises.
His documented interests included the Baltimore Iron Works, private lending, banking, milling, and transportation ventures (including bridges, canals, and evenutally a railroad).
His surviving correspondence demonstrates continuing attention to investment performance, debt collection, rents, bank dividends, land values, agricultural conditions, and broader economic developments.
By around 1800, the larger Carroll property portfolio extended across Maryland and into Pennsylvania and New York.
This does not mean Carroll personally created all of the wealth he controlled. Much of his economic platform was inherited.
The more important question for this project is what he did with that inherited platform.
He diversified it, managed it and optimized the overall performance.
He also used it to finance other ventures.
And increasingly he directed capital toward systems intended to improve the movement of goods, people, and commerce.
Transportation and Internal Improvements
From Rivers to Railroads
Carroll’s interest in transportation predates the Baltimore & Ohio Railroad by decades.\
He subscribed significant capital to efforts to improve navigation on the Potomac and participated in Maryland efforts involving the Susquehanna. The Potomac project eventually developed into the Chesapeake & Ohio Canal movement.
These ventures reflected a basic economic problem facing the young United States.
The country possessed enormous agricultural and natural resources, but those resources had limited value unless producers could reach markets economically.
Transportation therefore became an economic multiplier.
Carroll understood this from experience.
He had watched, and benefitted from, farms connected to mills around the Patapsco.
He had participated in regional commerce.
He had invested in land whose value depended partly upon access.
He invested in ventures that complemented each other, such as iron forges, bridges, and canals, all catering to the same need.
He had lent money and invested in banks whose success depended upon expanding commercial activity.
Transportation was not separate from these investments.
It connected them.
Banking and Capital
Carroll also became increasingly involved in banking and finance as the American economy developed beyond colonial forms of private lending.
He owned bank shares and followed national debates surrounding financial institutions closely.
He helped found the Bank of Maryland and was involved with the First and Second Bank of the United States. By 1820 he reported holding 236 shares in the Bank of Columbia and described bank dividends, rents, and interest payments as important components of his income.
This provides another connection between the earlier and later Carroll.
In colonial Maryland, wealthy individuals frequently functioned as private lenders because formal banking institutions scarcely existed.
By Carroll’s later life, banks increasingly performed those capital-allocation functions.
Carroll participated in both worlds.
His 95-year lifespan therefore overlaps not only the transition from colony to nation, but also the transition from a largely land-and-credit economy to one increasingly organized around banks, corporations, industrial enterprises, and large infrastructure projects.
Liberty and Slavery
Any interpretation of Charles Carroll’s accomplishments must acknowledge that slavery was deeply embedded in the system that created and sustained his wealth. Doughoregan Manor and other Carroll properties depended extensively upon enslaved labor.
The contradiction is unavoidable.
Carroll was a forceful advocate of political liberty and the only Catholic signer of the Declaration, yet he denied liberty to hundreds of people held in bondage within his own economic system.
He did take actions that demonstrate some recognition of the problem.
In 1797 he introduced unsuccessful legislation for the gradual abolition of slavery in Maryland according to the Maryland State Archives although there are questions about this claim.
He expressed is point of view in letters he wrote. “ .. why keep alive the question of slavery? It is admitted by all to be a great evil.” This example from 1825.
Later he became associated with the American Colonization Society as he sought practical ways to support its gradual abolition through resettlement.
But Carroll did not abolish slavery on his own estates during his lifetime.
The project therefore treats slavery neither as a footnote nor as a reason to disregard the rest of his career. It is part of the same history.
Carroll’s life illustrates one of the central contradictions of the American founding. A nation could articulate extraordinary principles of liberty while continuing to maintain systems fundamentally incompatible with those principles.
1800–1827
From Politician to System-Builder
Carroll largely withdrew from elective politics around 1800. He did not withdraw from public affairs.
Carroll still possessed an exceptionally disciplined and agile mind, retaining his keen judgment, intellectual curiosity, and remarkable memory well into his nineties.
For the next quarter century, he continued to manage property, evaluate investments, participate in enterprises, correspond with national leaders, follow political developments, and support institutional projects.
His letters and business ledgers are a fascinating lens into the management and operations of a large decentralized enterprise from that period of time.
His interests increasingly mirrored the developing American economy. He achieved great success, though he was not without mistakes. While most of his investments were profitable, some were not.
For instance, his participation in the Alum Works Company turned out to be an unsuccessful venture.
That is useful to, and supports, the entrepreneurial interpretation.
Carroll was never simply an heir protecting inherited wealth.
Constantly in search of more effective and efficient ways to reach markets, he continued placing capital into ventures whose outcomes were uncertain.
By the mid-1820s, however, the transportation problem facing Baltimore (the port most of business depended on) had become urgent as the country was expanding westward and the competition to reach it was significant. Faster, more capable, and reliable transport systems were needed.
1825–1827
Baltimore's Impossible Challenge
The completion of the Erie Canal in 1825 fundamentally changed American transportation.
New York now possessed an efficient commercial route connecting the Atlantic with the interior.
By 1826, approximately 19,000 boats had already transported goods between the Midwest and New York. The cost of shipping freight from Buffalo to New York via canal decreased to around $10 per ton, compared to $100 per ton by road, representing roughly a 90% reduction. It was also faster.
Steamboats rendered the Mississippi River navigable, enhancing the value and urgency of accessing the Ohio River to reach the interior.
Philadelphia was developing a competing public works system designed to link Philadelphia to Pittsburgh and the Ohio River headwaters
Washington's ports (Alexandria and Georgetown) were backing the Chesapeake & Ohio (C&O) Canal, resurrecting George Washington’s decades old venture, after they had lost about half of their export trade.
Baltimore faced the possibility of losing western commerce to its competitors. Erie Canal trade was already drawing business away from the port and other Canals were being planned closer to home.
Baltimore's deep water port was an advantage being further inland by over 100 miles then the other major ports.
But the Patapsco River was not suitable for a western canal and the canal routes to the north and south were already claimed by competitors.
Baltimore’s merchants and civic leaders therefore proposed something extraordinary:
A railroad from Baltimore toward the Ohio River.
Railroads existed elsewhere, particularly in Britain, but the technology was immature. Those railroads were short distances and flat.
Nobody had demonstrated that a railroad could successfully cross the distances and mountainous terrain contemplated by the B&O Railroad.
From a modern perspective, the project resembled an enormous technological startup.
The market opportunity was clear.
The technology was not.
The route was uncertain.
The engineering challenges were immense.
The required capital was substantial.
And no established American railroad industry existed to provide a proven model.
Yet Baltimore moved forward.
1827–1828
The Baltimore & Ohio Railroad
The Baltimore & Ohio Railroad was chartered in 1827. Charles Carroll of Carrollton became a member of its first Board of Directors.
His involvement was partly practical and partly symbolic. Few Americans possessed greater public credibility. Carroll represented business success, wealth, political legitimacy, revolutionary prestige, and the founding generation itself.
He was a living legend by now .. the only signer of the declaration still alive when Adams and Jefferson both passed away on the same day (July 4, 1826).
The railroad also fit naturally within the pattern of his earlier life. For decades he had supported systems intended to connect production with markets.
The B&O proposed to accomplish that at an entirely different scale. Instead of improving a river or building a road, Baltimore proposed creating an entirely new transportation network.
Then came the ceremony that defines the final phase of the Carroll project.
July 4, 1828
The First Stone
The B&O selected July 4, 1828, to begin construction. The date was deliberate.
Fifty-two years had passed since the Declaration of Independence. Charles Carroll was now 90 years old. He was chosen to perform the ceremonial act of laying the railroad’s First Stone.
The historical symbolism is difficult to improve upon.
In 1776, Carroll had helped establish the country’s political independence by lending his name to the Declaration of Independence.
In 1828, he helped establish credibility for an never before attempted project designed to strengthen its economic independence by lending at same name.
The connection was not merely ceremonial. The railroad addressed one of the fundamental problems Carroll had encountered throughout his economic life:
How do you connect resources with markets?
The B&O Railroad represented a radically new answer by attempting to connect Baltimore to the Ohio River at Wheeling, West Virginia (then Virginia).
Railroad construction proceeded west from Baltimore through the Patapsco Valley.
In 1830 the railroad reached Ellicott’s Mills completing the first 13 miles.
Nearly sixty years earlier, Carroll had watched the Ellicotts establish the milling community and help transform the surrounding agricultural economy.
The B&O Railroad reached Wheeling in 1853, completing it's original mission.
The C&O Canal reached Cumberland in 1850, eight years after the B&O did.
The C&O Canal never reached the Ohio River.
Now a new transportation technology connected that same industrial corridor directly with Baltimore.
1829–1831
Philanthropy and Institutional Legacy
Carroll’s final years also demonstrate another form of long-term investment. Education and religion had shaped his own life profoundly. Carroll gave to his faith throughout his life and supported numerous churches and Catholic institutions financially and in other ways.
Notably, during the 1780s with his cousin Daniel Carroll, he supported efforts to establish a Catholic college at Georgetown (Georgetown University).
Near the end of his life he provided substantial support for St. Charles College near Doughoregan Manor, intended to educate Catholic clergy. He donated land and financial assets to the institution. In July 1831, at approximately 93 years old, Carroll participated in laying its cornerstone.
There is an important symmetry here. The young Carroll had been sent abroad because opportunities for Catholic education in colonial America were limited.
The elderly Carroll used his own resources to help create those opportunities in the United States.
1832
The Last Signer
Charles Carroll of Carrollton died in Baltimore on November 14, 1832 at the Lombard Street home of his daughter, Mary Caton, in Baltimore, He was 95 years old.
His death marked the final closing of the Revolutionary generation. There was national mourning upon his passing. Flags across Maryland were lowered, courts were adjourned, and President Andrew Jackson ordered all federal government offices in Washington to close as a mark of supreme respect.
The funeral Mass was celebrated three days later, on November 17, 1832, with immense solemnity. It took place at the Baltimore Cathedral, now known as the Basilica of the National Shrine of the Assumption of the Blessed Virgin Mary. The service was packed with high-ranking dignitaries, including the Governor and Senators of Maryland, the Mayor and City Council of Baltimore, U.S. Congressmen, and aging Revolutionary War veterans.
The funeral procession departed the Basilica in a severe storm. The solemn procession moved through four hours of constant, pouring rain. Despite the miserable weather, the procession pressed on in absolute silence to honor the nation's last living patriot.
The funeral procession continued by B&O train from Baltimore to Ellicott's Mills where his remains were returned to Doughoregan Manor and interred in the family chapel there.
The country he left behind bore little resemblance to the colony in which he had been born.
When Carroll entered the world, Maryland Catholics could not participate fully in public life.
When he died, he was remembered nationally as one of the founders of the republic.
When he was young, Maryland’s economy revolved heavily around plantations, tobacco, private credit, sailing vessels, and poor roads.
When he died, banks, corporations, manufacturing, canals, steamboats, turnpikes, and railroads were transforming the economy.
Carroll had participated in both worlds.
The Best Form of Entrepreneurship
He left a very public imprint. Carroll’s name and memory appears in many forms .. way too many to list them all here. Not all legacy is contained in speeches, statues, buildings, schools, forts, bridges, monuments or famous moments.
And the best entrepreneurship is not merely inventive, it is durable. In some cases, it can even be monumental. The monuments named after him are too numerous to list.
That may be the best test of entrepreneurship in the deepest sense.
Not simply whether you were bold enough to begin, but whether what you helped build was strong enough to last.
Carroll’s faith lasted.
His family platform evolved and lasted.
The republic lasted.
The railroad age he lived long enough to help launch lasted.
That is one last reason why Charles Carroll of Carrollton can be seen as America’s First Entrepreneur .. not only because he took the risks, but because he built for permanence.
Project Status
Currently, live historical presentations covering the remarkable life of America’s founding-era entrepreneur are happening thoughout the rest of 2026.
Coming in early 2027, a well researched book with recently discovered information, unpublished stories and a new point of view will be published and made available through wherever books are sold. Those details will be made available as we get closer to 2027.
