James Greenleaf

James Greenleaf (June 9, 1765 – September 17, 1843) was a late 18th and early 19th century American land speculator responsible for the development of Washington, D.C., after the city was designated as the nation's capital following passage of the Residence Act in 1790. A member of a prominent and wealthy Boston family, he married a Dutch noblewoman, who he later abandoned and then divorced, and served briefly as consul at the United States embassy in Amsterdam.

After his return to the United States, Greenleaf engaged in land speculation in Washington, D.C., New York state, and other areas. His land business collapsed in 1797, and he spent a year in debtor's prison. He married a wealthy Pennsylvania heiress after his release, and spent the remainder of his life in genteel poverty, fending off lawsuits.

Early life and education Greenleaf was born on June 9, 1765, in Boston, Massachusetts to William and Mary (Brown) Greenleaf. He was the 12th of 15 children.

Greenleaf was a member of the committee of correspondence, which communicated secretly with other cities regarding British policy and military actions and was a core base of support for the American Revolution. In July 1776, following the signing of the Declaration of Independence, Greenleaf announced American independence from the balcony of the Old State House in Boston. Among the crowd assembled for the announcement in Boston were John Quincy Adams and William Cranch. Adams was later elected President of the United States; Cranch was appointed as Chief Justice of the U.S. Circuit Court for the District of Columbia and the second Reporter of Decisions of the U.S. Supreme Court.

The Greenleaf family was among the best connected in early American history. Greenleaf's sister Rebecca married Noah Webster, who compiled the first American dictionary. Another of his sisters married Nathaniel Appleton, the minister and trustee of Harvard University. His sister Margaret married Thomas Dawes, a member of the Massachusetts Governor's Council, and his sister Abigail married William Cranch. The family's descendants also played a large role in American literature. The poet John Greenleaf Whittier was descended from James' great-grandfather Stephen. The 20th century poet T. S. Eliot was a descendant of Abigail Greenleaf Cranch. However, little is known about Greenleaf's early life or education. In 1781, when he was 16, his father retired from business and the Greenleaf family moved to New Bedford, Massachusetts.

Career In 1788, Greenleaf left Massachusetts and moved to Philadelphia, where Noah Webster introduced him to businessman James Watson. The two men established an import business, Watson & Greenleaf, with offices in Philadelphia and New York City.

After his business was incorporated, Greenleaf traveled to the Netherlands in the mid to late 1780s, where he tried to sell American bonds. According to John Quincy Adams, who was in Amsterdam at the same time, Greenleaf rented a magnificent mansion and immediately began circulating in high society in the city. He sold nearly two million bonds during this time and $160,000 worth of stock in the Bank of the United States, a central bank established by the U.S. federal government. He amassed a fortune worth $1 million, a very large sum at the time.

Washington, D.C. land speculation

Greenleaf arrived in Washington, D.C., on September 17, 1793

Greenleaf quickly ingratiated himself with several of Washington's closest friends, including Tobias Lear, who served as Washington's secretary from 1785 to June 1793. Greenleaf provided seed money for Lear's mercantile venture, Tobias Lear & Co., Greenleaf also associated with Thomas Johnson, who Washington had appointed as one of three commissioners of the District of Columbia. Greenleaf purchased of Johnson's land in Frederick County, Maryland for $14,000 in September 1793.

The Residence Act of 1790, which established the site for the nation's capital, provided for the appointment of three commissioners by the President without the need for Senate confirmation to govern the Washington, D.C., survey its land, purchase property from private landowners, and construct federal buildings. On September 23, 1793, Greenleaf purchased 3,000 city lots from the commissioners. The city offered him the lots at $66.50 each, a significant discount from the going price of $200 to $300 per lot. To raise money to improve the lots, Greenleaf executed a power of attorney on November 2, 1793, with Sylvanus Bourne, the American vice consul in Amsterdam. Bourne, who served as vice consul in Amsterdam under Greenleaf, was empowered to sell lots or obtain mortgages on them.

On November 19, 1793, Greenleaf moved into the Pearl Street home of Noah Webster in New York City.

The September 23 agreement with the commissioners was superseded by a subsequent agreement on December 24, 1793, with Greenleaf and his new business partner, Robert Morris. Morris was a Philadelphia merchant and one of 56 signatories to the Declaration of Independence and also to the Articles of Confederation and the United States Constitution. He was Chairman of the Pennsylvania Committee of Safety during the Revolutionary War, a delegate to the Second Continental Congress, and was appointed Superintendent of Finance for the U.S. Next to General George Washington, Morris was considered "the most powerful man in America." At the time he became Greenleaf's business partner, Morris also was one of Pennsylvania's original U.S. senators (his term ended in 1795).

Morris and Nicholson partnership

Greenleaf first approached his existing business partner, James Watson, with an offer to finance the purchase of the lots and the construction on them. Watson declined, and Greenleaf dissolved their partnership. Greenleaf then turned to Morris, then the richest man in America and a speculator in millions of acres of land.

Morris was already one of the most important land speculators in the Northeast. He purchased the western portion of the Phelps and Gorham Purchase. an area of western New York consisting of about —in March 1791 for $366,333.33. This area became known as Morris Reserve. Morris quickly sold of the reserve to The Pulteney Association in March 1791 for £75,000 for a profit of $216,128. This tract became known as the "Pulteney Tract".

Morris' association with Greenleaf started in February 1792, when Morris sold of the Morris Reserve to Greenleaf, Watson, and Andrew Craigie for £15,000 ($37,500). Morris sold another to the Holland Land Company between December 1792 and July 1793 for £112,500, and his son sold to the Holland Land Company for $500,000. Morris sold another (known as "the Triangle Tract") to an investor group in January 1793. By 1794, Morris was also an investor in the Virginia Yazoo Company, which was leveraging its political influence to purchase vast tracts of land from the state of Georgia (in what is the modern state of Mississippi) at low prices for land speculation.

Greenleaf and Morris purchased 6,000 lots under the same conditions as the September agreement. At least 1,500 of these lots were required to be in the northeast quadrant of Washington, D.C., but Greenleaf could take his pick of lots anywhere else in the city for the remainder. The monthly loan to the commissioners also increased to $2,660 per commissioner per month. The contract also included provisions identical to those in the September 23 contract, which required no down payment, did not require the first payment until May 1, 1794, required only annual payments of one-sixth of the total amount of the purchase price annually thereafter, and did not impose any interest. With these transactions, Greenleaf and his co-investors controlled about half the federal government's sellable land in Washington, D.C.

The December 24 contract with the city provided that Greenleaf and Morris could bring in a third partner, although the requirement to construct buildings was not binding on this partner. The partner they brought in was John Nicholson, who had served as comptroller general of Pennsylvania from 1782 to 1794. In 1792, Nicholson negotiated the purchase from the federal government of the tract known as the Erie Triangle. Along with an agent of the Holland Land Company, Aaron Burr, Robert Morris, and other individual and institutional investors, he formed the Pennsylvania Population Company. This organization, in turn, purchased all 390 parcels of land in the Erie Triangle. Nicholson was impeached in 1794 for his role in the company.

Financial strains and New York land speculation Greenleaf continued to expand his land holdings, purchasing of Anacostia River waterfront from various owners in December 1793, and near Alexandria, Virginia, in 1794. He also purchased 239.25 lots east of Georgetown from local landowners Uriah Forrest and Benjamin Stoddert. Another 1,000 lots of Notley Young's land were transferred to Greenleaf on April 24, 1794. Greenleaf bought out Watson's 25% interest in the Morris Reserve tract but was forced to sell his shares in the land to Oliver Phelps before the end of 1794.

Greenleaf's construction activities meant that, by 1794, he owned one third of the buildings for sale in Washington, D.C. Among the buildings he began constructing in that year were the four townhouses that became known as Wheat Row.

To finance these land acquisitions and construction activities, Greenleaf turned to Dutch financiers. Sources differ on whether Greenleaf traveled to the Netherlands in 1794 Whichever is the case, he was able to convince the Dutch government to pass legislation appointing agents and advocates for his business affairs. They began offering mortgages on the 6,000 Washington, D.C., lots. The guardians were authorized to accept mortgages not exceeding two million guilders ($8 million). But by July 1795, only 20,000 guilders ($80,000) had been raised.

Land deal with Aaron Burr

Greenleaf continued to be active in land speculation in New York state in addition to his speculation elsewhere in the U.S. In 1791, New York merchant Alexander Macomb purchased from New York state, a tract known as "Macomb's Purchase". Macomb sold to William Constable for £50,000 (in dollars). Six months later, Constable sold to banker Samuel Ward for £100,000 (in dollars). Constable and Ward agreed to sell to the British land speculator John Julius Angerstein. But New York state barred non-citizens from owning property in the state, so Constable and Ward argued that if the law was not changed they would buy the land back from Angerstein. The problem was that neither Constable nor Ward had the funds to do so. William Stephens Smith, son-in-law of President John Adams, held power of attorney for Angerstein, and in September 1794 he convinced Aaron Burr to buy of Angerstein's land for £24,000. Smith, in an obvious conflict of interest, assured Burr that he would provide half the sale price. But Smith withdrew from the purchase, leaving Burr to come up with the entire amount. Burr could not afford to do so. Either Ward or Burr (sources are unclear) sought out Greenleaf for financial assistance.

On November 25, 1794, Greenleaf agreed to contribute £12,000 (about $500,000 in 2012 inflation-adjusted dollars) to help Burr purchase Angerstein's land. But Greenleaf was deep in debt. He purchased a cargo of tea from Rhode Island merchant John Brown, whose family funded and lent its name to Brown University. Greenleaf paid for the cargo partly in cash, and took out a mortgage with Philip Livingston in 1795 on the Angerstein land to pay for the remainder. He served only about six weeks, returning to the U.S. on April 29, 1793. In October 1794, Greenleaf moved out of Webster's home in New York City after hosting a raucous party in the Webster home in October, leading Webster to demand that he move.

Land deal with Law Greenleaf returned to Washington, D.C., in December 1794, where he became acquainted with Thomas Law, a wealthy British merchant who had just arrived in America. Law was son of Edmund Law, the Bishop of Carlisle. Law's brother John Law was Bishop of Clonfert and Kilmacduagh and Bishop of Killala and Achonry, and in 1795 was named Bishop of Elphin. His brother Edward Law served as Lord Chief Justice of England and Wales from 1802 to 1818. Another brother, George Henry Law, became Bishop of Chester in 1812 and Bishop of Bath and Wells in 1824. Thomas Law spent years working for the East India Company in India, where he made a fortune in trade.

Law arrived in Washington, D.C., in the summer of 1794, and he met Greenleaf in November or December of that year. Law was deeply impressed with Greenleaf, On December 4, 1794, and Greenleaf sold 500 city lots to Law for £50,000 (or $133,000). The price per lot was $297.60, a 372 percent increase over the $80 per lot which Greenleaf, Morris, and Nicholson had paid for them a year earlier. As the French approached Amsterdam, a pro-French republican revolution overthrew William V of Orange on January 18, 1795. The Amsterdam banking and investment community was suddenly no longer in a position to back any distant investments.

Just when Greenleaf or his lenders learned of the Dutch revolution is unclear, but the war in Europe already placed Morris and Nicholson in deep financial trouble by 1794. Many European companies and individuals which owed Morris money had declared bankruptcy, leaving Greenleaf with severe cash flow challenges.

On February 20, 1795, Greenleaf, Morris, and Nicholson formed the North American Land Company (NALC) to finance their land speculation business. The three partners turned over to the company land throughout the U.S. totaling more than , most of it valued at about 50 cents an acre. in Kentucky, in North Carolina, in Pennsylvania, in South Carolina, and in Virginia. NALC was authorized to issue 30,000 shares, each worth $100. Greenleaf, Morris, and Nicholson were entitled to receive a 2.5 percent commission on any land the company sold. Greenleaf was named secretary of the new company. On May 15, 1795, Washington, D.C., commissioners demanded their first payment from Greenleaf, Morris, and Nicholson for the 6,000 lots purchased in 1793. But Greenleaf had misappropriated some of the company's income to pay his own debts. Without the Dutch mortgage income and missing funds, there was no money to make the payment to the commissioners. Greenleaf also had co-signed for loans taken out by Morris and Nicholson. When these men defaulted, creditors sought Greenleaf to make good on all the debts, and he could not.

On July 10, 1795, Morris and Nicholson bought out Greenleaf's interest in the December 24, 1793, agreement. The commissioners began legal proceedings to regain title to the 6,000 lots owned by NALC and the 1,115.25

On September 30, 1796, Greenleaf placed 7,455 of his NALC shares in a trust known as the "391 trust" because it was recorded on page 391 of the firm's accounting book. The 391 trust was created to generate income from the 6% dividend to pay a loan given to Greenleaf by Edward Fox. A trustee was assigned to hold on to the shares. The same day, Greenleaf put 2,545 shares into another trust (the "381 trust"), as a guarantee against nonpayment of the dividend by Morris and Nicholson. Morris and Nicholson's made the first payment to Greenleaf for the one-third interest in the NALC by turning over title to several hundred lots in Washington, D.C. On March 8, 1797, Greenleaf executed the 381 trust. When the NALC did not issue its 6% dividend, Greenleaf transferred a third of the shares in the 391 trust to the trustees. The total number of shares transferred to the "381 trust" trustees was now 6,119.

On June 26, 1797, Greenleaf, Morris, Nicholson, and the trustees of the 381 and 391 trusts executed a new agreement creating an aggregate fund. Morris and Nicholson turned over all their Washington, D.C., real estate and all their NALC shares to the fund. Greenleaf later purchased 541 NALC shares on the open market and was again elected secretary of the company. With poor business practices dragging down NALC, Morris and Nicholson acting as personal guarantors of each other's notes, and many of these notes coming due, neither man was able to pay them. Creditors began selling the notes publicly, often at steeply discounted prices. His debt was eventually discharged, and he was released on August 30, 1798, having served less than a year. Nicholson died in prison on December 5, 1800. Morris was released on August 26, 1801, Morris and Nicholson honestly believed that, if their cash flow problems were resolved, they could make payments on the property they owned and their shares would be returned to them. But this proved incorrect. On October 23, 1807, all stock in the company was sold at seven cents on the dollar to accountants managing the aggregate fund. By 1856, the company had produced just over $92,000 in income. Morris and Nicholson's heirs sued to recover the stock and gain access to the income; in 1880, each estate was awarded $9,962.49. Pratt v. Law & Campbell, 13 U.S. 456 (1815) Greenleaf v. Cook, 15 U.S. 13 (1817) Bayley v. Greenleaf, 20 U.S. 46 (1822) Greenleaf v. Queen, 26 U.S. 138 (1828) Greenleaf's Lessee v. Birth, 30 U.S. 132 (1831) Greenleaf v. Birth, 34 U.S. 292 (1835) Potomac Steamboat Co. v. Upper Potomac Steamboat Co., 109 U.S. 672 (1884)

Yet another case, Morris v. United States, 174 U.S. 196 (1899), involved a suit against the estate of Robert Morris, and helped resolve a long-running boundary dispute in Washington, D.C. The case discusses Greenleaf, Nicholson, and Morris' involvement in selling lots on Water Street in the city.

Return to Washington, D.C. Grave marker of James Greenleaf in Congressional Cemetery in Washington, D.C. As early as 1816 or 1817, Greenleaf made known to his wife, who was residing in their Allentown, Pennsylvania residence, his desire to return to Washington, D.C., full-time. Ann Greenleaf, however, expressed her unwillingness to leave Allentown. In an 1817 letter to her friend and trustee, William Tilghman, she wrote:

It would be unkind of me to say to Mr. Greenleaf, that I never shall be reconciled to a residence in Washington, D.C., and I believe that he does not suspect that such are my sentiments, but I say to you my dear Sir unhesitatingly, that I dislike Washington...I love retirement, particularly the retirement of Allentown.

Although he was not estranged from his wife,

The final years of Greenleaf's life were spent quietly. His few financial needs were met by his wife and by speaking fees. By the late 1830s, he had paid off or otherwise resolved almost all his debts and had extensive land holdings, though little of it was developed. He associated with childhood friends John Quincy Adams, William Cranch, and Cranch's wife Nancy, who was Greenleaf's sister, and attended the Unitarian Church. (Greenleaf owned 2,612 books, which was an extremely large library for the day.) When Greenleaf's sister, Nancy Cranch, died on September 16, 1843, however, he went into a state of shock on learning of her death. she died in Allentown on September 21, 1851. Her remains were later moved to North Laurel Hill Cemetery in Philadelphia. She was a member of a powerful Dutch banking family, and noble-born. Greenleaf said that, in 1796, he and the baroness had sex soon after his arrival in Amsterdam. He made it clear that neither had seduced the other. When he returned to the U.S., he learned she was pregnant. He claims he immediately returned to Amsterdam to marry her, and was told that she had miscarried. The van Aschat family convinced him to marry her anyway, and he did so in 1788. Greenleaf said that his wife's maid soon revealed that there had been no pregnancy. By this time, the baroness was pregnant, and she gave birth to a son. Greenleaf says his wife later tried to commit suicide after which he separated from her. Greenleaf returned to the U.S., and a judge in Rhode Island granted him a divorce on September 3, 1796.

Greenleaf's contemporaries and modern historians dispute his account of his marriage and divorce. Historian Allen Clark, who in the late 19th century interviewed Greenleaf's contemporaries, dismissed the account of deception and said that the couple fell in love and, after a three-month romance, married. But Greenleaf's critics in the 1820s and 1830s said Greenleaf seduced the baroness to gain access to Dutch banking circles and capital for real estate investing.

James and Antonia had two children before their marriage ended: William Christian James Greenleaf, born September 6, 1790, and Marie Josephine Wilhelmina Matilda Greenleaf (no date of birth known).

Greenleaf's land and financial speculations ruptured his relationships with his family, But by early 1795, Greenleaf mended his personal relationship with his old business partner, James Watson, and with other business associates in New York City. He also was reconciled with his sister Rebecca. possibly because it was considered the halfway point between Washington, D.C., and New York City. On March 9, 1795, Greenleaf purchased the Landsdowne estate of John Penn, the last colonial governor of Pennsylvania, for $37,000. Penn built a luxurious mansion on the estate in or around 1773, and died February 9, 1795. Then, on April 15, 1795, Greenleaf purchased General Philemon Dickinson's house on Chestnut Street, on a corner opposite Robert Morris' home, in Philadelphia for $28,000. Greenleaf held lavish parties at both homes.

By late 1797, Greenleaf was on the verge of bankruptcy. But there was no national bankruptcy law. Congress did not pass one until the Bankruptcy Act of 1800, so Greenleaf was forced to apply for bankruptcy in each state where he had conducted business. He first applied for bankruptcy in Pennsylvania on March 10, 1798, although his debts were not settled and his case was not discharged there until March 1804. He then applied for bankruptcy in Maryland on February 9, 1799, and his case was discharged on August 30. In 1802, Greenleaf applied for bankruptcy under the new federal bankruptcy law. His federal case was discharged on March 17, 1804.

Second marriage

While Greenleaf was in bankruptcy court, he married his second wife, Ann Penn Allen (nicknamed "Nancy"), on April 26, 1800. Allen was known to Greenleaf as early as 1795; Thomas Law mentioned her in a letter about Greenleaf that year. She came from a wealthy and famous family; her father was James Allen, a prominent businessman and political figure in Allentown. Her grandfather was William Allen, former Chief Justice of the Supreme Court of Pennsylvania and founder of Allentown. Her mother was Elizabeth Lawrence, daughter of Tench Francis Sr., a prominent lawyer in colonial Maryland and Pennsylvania, and her uncle was Sir Philip Francis, the Irish-born British politician and political pamphleteer who authored the Letters of Junius. Margaret's marriage to Dale was a short one. Her parents forbade her to marry, but she eloped. The couple returned to Allentown, where Ann Greenleaf all but imprisoned her daughter in the Greenleaf home and refused Dale entry. Dale forced his way into the Greenleaf home, and James had him arrested. The disgrace of imprisonment proved too much for Dale, who committed suicide after his short imprisonment. Margaret, who was pregnant with Dale's child, gave birth to a son, Allen, in 1833. Allen Dale accidentally drowned in the Delaware and Raritan Canal in 1895. Margaret died in 1898.

The primary Greenleaf home from 1800 to 1807 was a large mansion in Allentown located at the corner of 5th and Hamilton Streets. It was situated in a small park full of trees, and the Greenleafs entertained lavishly and frequently there. Although Greenleaf lived comfortably on his wife's income, in 1810 and he returned to Washington regularly to defend himself in these cases. Little of Greenleaf Point was developed by the time Greenleaf was forced into bankruptcy. The city grew not on Greenleaf Point, as he anticipated, but around the White House, around the United States Capitol, and between the White House and Georgetown. By 1800, Greenleaf Point was still almost completely undeveloped. The only finished road through the area was New Jersey Avenue, on which two large buildings were constructed. Twenty half-finished structures, begun by Greenleaf, clustered around high land on South Capitol Street. The city's first Methodist church meeting was held in one of the "20 Buildings" in 1802. By 1824, however, the 20 Buildings were in ruins.

Another historic structure erected by Greenleaf was what is now known as the Thomas Law House, built in 1795 on 6th Street SW. Thomas Law and his new wife Elizabeth Parke Custis Law lived there from March through August 1796 after their marriage, and while waiting for their own house to be completed. This structure still stands in 2012, and has been listed on the National Register of Historic Places since 1973. It is one of the few early Federal-style houses still standing.

Greenleaf also at one time owned the land on which the Washington Arsenal and the District of Columbia Penitentiary were later built. In 1871, an existing red brick schoolhouse at that location was renamed the "Greenleaf Building" a name "suggested by [its] location" in the Greenleaf part of Washington. That building was replaced in 1896, but in later school documents, as early as 1909, it was referred to as the "James Greenleaf School". The school was razed in 1960.

Greenleaf also played important roles in American politics and literature. He bankrolled Noah Webster's newspaper, American Minerva. This newspaper played an important role in supporting the Federalist political movement in the 1790s. Greenleaf also provided critical financial support to Noah Webster during Webster's financially distressed early years. Without such support, Webster would have been unable to continue writing or sustain his interest in his dictionary.

Although James Greenleaf is not well-remembered two centuries after he was most active in business, historians Thomas P. Abernethy and Wendell H. Stephenson nevertheless call Greenleaf "the most important land speculator that the United States has produced."