James Greenleaf

James Greenleaf
James Greenleaf, painted by Gilbert Stuart in 1795
Born	(1765-06-09)June 9, 1765 Boston, Massachusetts, U.S.
Died	September 17, 1843(1843-09-17) (aged 78) Washington, D.C., U.S.
Nationality	American
Occupation	Land speculator
Known for	Developing Washington, D.C.

James Greenleaf (June 9, 1765 – September 17, 1843) was an important early American land speculator. A member of a prominent and wealthy Boston family, he married a Dutch noblewoman (whom he later abandoned and then divorced) and was briefly consul at the United States embassy in Amsterdam. Returning to the United States, he engaged in land speculation in the District of Columbia, New York state, and other areas. He was a central figure in the early development of Washington, D.C. 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

James Greenleaf was born on June 9, 1765, in Boston, Massachusetts, in the United States to William and Mary (Brown) Greenleaf.^[1][2] He was the 12th of 15 children.^[3] His father was William Greenleaf, a merchant who was later appointed sheriff of Suffolk County, Massachusetts during the American Revolutionary War.^[3] and was a member of the committee of correspondence which secretly communicated with other cities regarding British policy and military actions in the years prior to the American Revolution.^[4] William Greenleaf announced American independence in July 1776 from the balcony of the Old State House. In the crowd were John Quincy Adams and William Cranch. Adams would later be President of the United States; Cranch would be chief judge of the District of Columbia circuit court and the second reporter of decisions of the Supreme Court of the United States.^[4] The Greenleafs were Huguenots who fled France, anglicizing their family name (Feuillevert) to Greenleaf. Greenleaf's great-great-grandfather, Edmund, was born in 1574 in Ipswich, Suffolk, England. His great-grandfather, Stephen, was born there in 1628, and the entire family emigrated to Newbury, Massachusetts, in 1635.^[5]

The Greenleaf family became one of the best connected in early American history. His sister, Rebecca, married Noah Webster (who created the first American dictionary). Another married Nathaniel Appleton, the noted minister and a trustee of Harvard University. His sister Margaret married Thomas Dawes, a member of the powerful Massachusetts Governor's Council, while his sister Abigail married William Cranch. The family's descendants also played a large role in American literature. The celebrated 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.^[6]

Little is known about Greenleaf's early life or education. In 1781, when James was 16, his father retired from business and the Greenleaf family moved to New Bedford, Massachusetts. Seven years later, Greenleaf left Massachusetts and moved to Philadelphia, Pennsylvania. Noah Webster introduced him to businessman James Watson,^[7] and the two men established an import business, Watson & Greenleaf. The firm had offices in Philadelphia and New York City.^[8]

After his business was incorporated, Greenleaf traveled to the Netherlands, where he tried to sell American bonds.^[9][10] 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.^[8] Greenleaf was in Amsterdam from January 31, 1789, through August 1793, where he conducted business with Daniel Crommelin & Sons (a major Dutch investment banking house marketing American bonds).^[11] He sold nearly two million bonds during this time, as well as $160,000 worth of stock in the Bank of the United States (a central bank established by the United States federal government).^[12] He amassed a fortune worth $1 million, a very large sum at the time.^[13][14][15]

First marriage

Greenleaf married Baroness Antonia Cornelia Elbertine Scholten van Aschat et Oud-Haarlem in 1788.^[12][16] She was a member of a powerful Dutch banking family, and noble-born.^[17] Greenleaf said that, in 1796, he and the baroness made love soon after his arrival in Amsterdam. (He made it clear that neither had seduced the other.) When he returned to the United States, 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 also says 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.^[17] During his brief marriage, Greenleaf communicated to Noah Webster how unhappy he was with the baroness.^[18] Greenleaf returned to the United States, and a judge in Rhode Island granted him a divorce on September 3, 1796.^[19]

Greenleaf's contemporaries and modern historians dispute Greenleaf's account of his marriage and divorce. Historian Allen Clark, who in the late 19th century interviewed contemporaries of Greenleaf's, dismissed the account of deception and said that the couple fell in love and, after a three-month romance, married.^[20] 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.^[17] There is dispute about the divorce as well. Historians Joseph Smith and Julius Goebel claim the baroness divorced Greenleaf (not the other way around).^[21]

What is not in dispute is that 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).^[12][22][23]

On March 2, 1793, Greenleaf was named consul at the United States embassy in Amsterdam.^[24][25] He served only about six weeks, returning to the United States on April 29, 1793.^[26]

Land speculation in Washington, D.C.

Greenleaf arrived in Washington, D.C., on September 17, 1793.^[27] He was present at the laying of the cornerstone of the United States Capitol on September 18,^[12][20] at which time he met President George Washington.^[28]

Greenleaf quickly ingratiated himself with several of Washington's closest friends.^[14] One of these was Tobias Lear, who had served as Washington's secretary from 1785 to June 1793.^[29] Greenleaf provided seed money for Lear's mercantile venture, Tobias Lear & Co.,^[12][14] in 1793.^[30] Another was Thomas Johnson, whom Washington had appointed as one of three commissioners of the District of Columbia. Greenleaf purchased 15,000 acres (61 km²) of Johnson's land in Frederick County, Maryland, for $14,000 in September.^[14][31]

The Residence Act of 1790, which established the site for the nation's capital, provided for the appointment of three commissioners by the President (and without the need for Senate confirmation) to govern the District of Columbia, survey its land, purchase property from private landowners, and construct federal buildings.^[32] On September 23, 1793, Greenleaf purchased 3,000 city lots from the commissioners.^[24][33] The city offered him the lots at $66.50 each,^[27][34] a significant discount from the going price of $200 to $300 per lot.^[14] To get this low price, Greenleaf was required to construct 70 homes on the lots before 1800, not sell any of the land before 1796, and lend the commissioners $2,200 a month until certain public buildings were constructed.^[35] 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.^[36]

On November 19, 1793, Greenleaf moved into the Pearl Street home of Noah Webster in New York City.^[37]

The September 23 agreement with the commissioners was superseded by a new one on December 24, 1793. For this agreement, Greenleaf had a new business partner, Robert Morris. Morris was already legendary in the United States. He was a merchant who signed the Declaration of Independence, the Articles of Confederation, and the United States Constitution. He was Chairman of the Pennsylvania Committee of Safety during the Revolutionary War, and was a delegate to the Second Continental Congress, and was Superintendent of Finance for the fledgling United States. Next to General George Washington, he was considered "the most powerful man in America."^[38] At the time he became Greenleaf's business partner, he was one of Pennsylvania's original U.S. senators (his term ended in 1795).

Partnering with Robert Morris and John Nicholson

Greenleaf first approached his existing business partner, James Watson, with an offer to finance the purchase of the lots and the construction thereon. Watson declined, and Greenleaf dissolved their partnership.^[39] 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^[40]—an area of western New York consisting of about 3,750,000 acres (15,200 km²)—in March 1791 for $366,333.33.^[41] This area now became known as the Morris Reserve. Morris quickly sold 1,000,000 acres (4,000 km²) of the reserve to The Pulteney Association in March 1791 for £75,000 (for a profit of $216,128).^[42] (This tract became known as the "Pulteney Tract".)

Morris' association with Greenleaf started in February 1792, when Morris sold 100,000 acres (400 km²) of the Morris Reserve to Greenleaf, Watson, and Andrew Craigie for £15,000 New York currency ($37,500).^[43] Morris sold another 1,000,000 acres (4,000 km²) to the Holland Land Company between December 1792 and July 1793 for £112,500, and his son sold 1,800,000 acres (7,300 km²) to the Holland Land Company for $500,000.^[44] Morris sold another 87,000 acres (350 km²) ("the Triangle Tract") to an investor group in January 1793.^[43][45] By 1794, Morris was also an investor in the Virginia Yazoo Company, which was using political influence to purchase from the state of Georgia vast tracts of land (in what is the modern state of Mississippi) at low prices for land speculation.^[12][46]

Greenleaf and Morris purchased 6,000 lots under the same conditions as the September agreement.^[47] At least 1,500 of these lots had to be in the northeast quadrant of the District of Columbia, 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.^[14] An additional clause required that the 6,000 lots include 428.5 lots on Buzzard Point owned by Notley Young (a plantation owner in Prince George's County, Maryland) and 220 lots on Buzzard Point owned by Daniel Carroll (a Founding Father and Maryland landowner whose farm was used to form the District of Columbia).^[48] 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.^[49] With these transactions, Greenleaf and his co-investors now controlled about half the federal government's salable land in the District of Columbia.^[50]

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.^[51] The partner they brought in was John Nicholson, who had served as comptroller-general of the state of Pennsylvania from 1782 to 1794. In 1792, Nicholson had negotiated the purchase from the federal government of the 202,000-acre (820 km²) 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 front organization purchased all 390 parcels of land in the Erie Triangle. Nicholson was impeached in 1794 for his role in the company.^[52]

Financial strains, and land speculation in New York state

Greenleaf continued to expand his land holdings. He purchased 2,101 acres (8.50 km²) of Anacostia River waterfront from various owners in December 1793, and purchased 295 acres (1.19 km²) near Alexandria, Virginia, in 1794.^[53] He also purchased 239.25 lots east of Georgetown from local landowners Uriah Forrest and Benjamin Stoddert.^[54][55] Another 1,000 lots of Notley Young's land were conveyed to Greenleaf on April 24, 1794.^[51] Greenleaf relied on his brother-in-law, Nathaniel Appleton, for assistance with his land purchases.^[12] But when Appleton fell ill in September 1794, Greenleaf summoned his brother-in-law and good friend William Cranch to D.C. to act as his sales agent.^[56][57] Greenleaf bought out James Watson's fourth-interest in the Morris Reserve tract, but was forced to sell his shares in the land to Oliver Phelps before the year was out.^[58]

Greenleaf's construction activities meant that by 1794 he owned one-third of the buildings for sale in the Washington, D.C. Among the buildings he began construction on that year were the four townhouses which became Wheat Row.^[59]

To finance these land acquisitions and construction activities, Greenleaf turned to Dutch financiers. Sources are in conflict as to whether Greenleaf traveled to the Netherlands in 1794^[12] or stayed in Philadelphia and New York City during the year.^[60] Whichever is the case, Greenleaf 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 D.C. lots. The guardians were authorized to accept mortgages not to exceed 2 million guilders ($8 million), but by July 1795 only 20,000 guilders ($80,000) had been raised.^[36] Greenleaf's old friend, Sylvanus Bourne, attempted to find mortagees in Rotterdam, but was no more successful there: Seeking 1 million guilders in loans, he secured just 150,000 guilders ($60,000).^[61]

Land deal with Aaron Burr

Greenleaf continued to be active in land speculation in New York state as well. In 1791, New York merchant Alexander Macomb purchased 4,000,000 acres (16,000 km²) from the state of New York (a tract known as "Macomb's Purchase"). Macomb sold 2,000,000 acres (8,100 km²) to William Constable for £50,000 (New York money). Six months later, Constable sold 1,000,000 acres (4,000 km²) to banker Samuel Ward for £100,000 pounds (New York money).^[62] Constable and Ward agreed to sell 2,000,000 acres (8,100 km²) to the British land speculator John Julius Angerstein. But New York state barred non-citizens from owning property in the state. Constable and Ward agreed 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 210,000 acres (850 km²)^[63][64][65] 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.^[63][66] On November 25, 1794,^[64] Greenleaf agreed to contribute £12,000 (about $500,000 in 2012 inflation-adjusted dollars) to help Burr purchase Angerstein's land.^[66] Constable and Ward conveyed the deed to Greenleaf in December 1794.^[67] But Greenleaf was deep in debt. He had purchased a cargo of tea from Rhode Island merchant John Brown (whose family funded and leant 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.^[63][64] But the purchase agreement with Constable and Ward/Angerstein barred the land from being mortgaged. Greenleaf now defaulted on his agreement to help Burr. Burr was now facing the loss of his own £12,000 as well as the Angerstein property. Angerstein was unhappy as well. He was upset not only that Ward had sold 210,000 acres (85,000 ha) but also that Greenleaf had mortgaged the property. Angerstein hired attorney Alexander Hamilton (who had just resigned as Secretary of the Treasury) to press his case in America. A series of suits and countersuits lasting years followed, causing increasingly bad feelings between Burr and Hamilton.^[66] (Burr dueled with Hamilton over other issues on July 11, 1804. Hamilton was killed.) For his part, Greenleaf was unable to make his mortgage payments on the Angerstein land, and Livingston foreclosed in December 1798. Brown bought the mortgage for $33,000.^[64] (These 210,000 acres (85,000 ha) thus became known as Brown's Tract.)^[63]

In October 1794, Greenleaf moved out of Noah Webster's home in New York City. Rumors about Greenleaf's poor financial situation were made known to Noah Webster. When Greenleaf hosted a raucous party in the Webster home in October, Webster demanded that he move out.^[68]

Land deal with Thomas Law

Greenleaf was back in Washington, D.C., in December 1794. He became acquainted with Thomas Law, a wealthy British merchant newly arrived in America. Law was the son of Edmund Law, the Bishop of Carlisle. His 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, 1st Baron Ellenborough, 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 many years in India, where he made a fortune in trade.^[69]

Law arrived Washington in the summer of 1794.^[70] He met Greenleaf in November or December 1794 and was deeply impressed with him.^[71] On December 4, 1794,^[72] 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 just a year earlier.^[12]

War in Europe and formation of the North American Land Company

Although Greenleaf continued to purchase land by promising that Dutch loans would be forthcoming, the prospect of Dutch money came to an end in January 1795. A coalition of states (the "First Coalition") had formed in 1793 to invade Revolutionary France and bring down the French First Republic. One of the largest of the First Coalition armies gathered along the Franco-Belgian border. Initial success by the First Coalition turned to stalemate, and France counterattacked by invading Belgium and the Netherlands in March 1794 in what became known as the Flanders Campaign. A majority of the Dutch people supported the French invasion, believing that this would mean the end of the authoritarian Orangist government.^[73] As the French approached Amsterdam, a pro-French republican revolution overthrew William V of Orange on January 18, 1795.^[74] The Amsterdam banking and investment community was suddenly no longer in a position to back any distant investment schemes.^[24][75]

Just when Greenleaf or his lenders knew of the Dutch revolution is unclear, but the war in Europe had already put Morris and Nicholson in deep financial trouble by 1794.^[76] Many of the European companies and individuals which owed Morris money were now bankrupt, leaving him with severe cash flow difficulties.^[77]

On February 20, 1795, Greenleaf, Morris, and Nicholson formed the North American Land Company (NALC) to finance their land speculation business.^[2][12] According to one historian of American land speculation, the NALC was "largest land trust ever known in America".^[78] The three partners turned over to the company land throughout the United States totaling more than 6,000,000 acres (24,000 km²), most of it valued at about 50 cents an acre.^[12] In addition to land in the District of Columbia, there were 2,314,796 acres (9,367.65 km²) in Georgia,^[79] 431,043 acres (1,744.37 km²) in Kentucky, 717,249 acres (2,902.60 km²) in North Carolina, 647,076 acres (2,618.62 km²) in Pennsylvania, 957,238 acres (3,873.80 km²) in South Carolina, and 932,621 acres (3,774.18 km²) in Virginia.^[80] NALC was authorized to issue 30,000 shares, each worth $100.^[12]

To encourage investors to purchase shares, the three partners guaranteed that a 6 percent dividend would be paid every year. To ensure that there was enough money to pay this divided, each partner agreed to put 3,000 of their own NALC shares in escrow.^[3][81] 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.^[3]

Collapse of the North American Land Company

The NALC encountered financial difficulty almost immediately. Only 4,479,317 acres (18,127.15 km²) of land was turned over to the NALC, which meant it could issue only 22,365 shares. This meant only 7,455 shares were put into escrow (instead of the required 9,000). Rather than paying creditors with cash, the NALC paid them with shares (8,477 shares in 1795 and 1796).^[82] On May 15, 1795, the 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. Furthermore, Greenleaf had co-signed for loans taken out by Morris and Nicholson. When these men defaulted, creditors sought out Greenleaf to make good on the debts—which he could not.^[83]

On July 10, 1795, Morris and Nicholson bought out Greenleaf's interest in the December 24, 1793, agreement.^[84] The commissioners began legal proceedings to regain title to the 6,000 lots owned by NALC and the 1,115.25^[54] lots owned by Greenleaf personally. The worsening financial problems of Greenleaf, Morris, and Nicholson led to increasingly poor personal relations among the three men.^[75] Nicholson, particularly bitter, began making public accusations against Greenleaf in print.^[75] Morris attempted to mediate between the two men, but his efforts failed.^[12]

In an attempt to resolve his financial problems, Greenleaf sold his shares in the NALC to Nicholson and Morris on May 28, 1796, for $1.5 million.^[82] Unfortunately, Morris and Nicholson funded their purchase by giving Greenleaf personal notes.^[3] Furthermore, they endorsed one another's notes.^[75] Morris and Nicholson, themselves nearly bankrupt, agreed to pay one-quarter of the purchase price every year for the next for years. Greenleaf's shares were not to be transferred to Morris and Nicholson until the fourth payment was received.^[82]

Although Greenleaf had a net worth of $5 million (about $1.5 billion in inflation-adjusted 2010 dollars) in 1796, he was having trouble raising the cash to meet his obligations. Land sales were not occurring fast enough or at prices high enough to allow him to meet his debt payments. He offered Alexander Hamilton $1 million in July 1796 if Hamilton would lend his name and reputation to Greenleaf's attempt to raise money. Hamilton refused.^[85]

On September 30, 1796, James Greenleaf put 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 percent 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.^[86] 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.^[87] When the NALC did not issue its 6 percent dividend, Greenleaf transferred one-third of the shares in the "391 trust" to the trustees.^[88] The total number of shares transferred to the "381 trust" trustees was now 6,119.^[89]

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 D.C. real estate and all their NALC shares to the Aggregate Fund.^[77] The Aggregate Fund (which now held the vast bulk of the NALC's shares) was created to administer the NALC for the benefit of the 381 and 391 trusts. The Aggregate Fund was also to pay the debts owed to the D.C. commissioners and to Daniel Carroll, as well as $900,000 in debt incurred by Greenleaf.^[90][91] Greenleaf later purchased 541 NALC shares on the open market and was elected secretary of the company again.^[89]

Morris attempted to keep the NALC afloat. He sent agents throughout Europe to try to find investors, but found few takers.^[92]

Poor business practices were now dragging down NALC. For years, Morris and Nicholson had acted as personal guarantors for one another's notes. Now many of these notes were coming due, and neither man could pay them. Creditors began selling the notes publicly, often at heavy discounts.^[76] By 1798, Morris and Nicholson's $10 million in personal notes were trading at one-eighth their face value.^[77] NALC also discovered that some of titles to the 6,000,000 acres (24,000 km²) of land it owned were not clear, and thus the land could not be used for security. In other cases, NALC found it had been swindled, and the rich land it thought it owned turned out to be barren and worthless.^[76]

Debtor's prison

His funds exhausted and unable to pay just a single debt, James Greenleaf was sentenced to serve time in the Philadelphia Debtors' Prison. Although the exact date that he entered debtor's prison in 1797 is not known, he was definitely incarcerated by October 18, 1797.^[93]:74–75 His debt was eventually discharged, and he was released on August 30, 1798 (having served less than a year).^[94]:227

Morris and Nicholson were able to avoid debtor's prison for a time. Both men fled to their homes in Philadelphia. At the time, individuals serving notice of a court suit had to deliver the notice personally. So long as both men remained inside their homes, they could not be served—and thus could avoid being sued. For several years, creditors' agents camped out on Morris and Nicholson's doorsteps and in their gardens. Eventually both men were finally served, and both were sentenced to debtor's prison. Morris entered prison on February 16, 1798, and Nicholson in the summer of 1799.^[77][95] Nicholson died in prison on December 5, 1800.^[96] Morris left prison on August 26, 1801,^[75] and died a penniless and broken man in 1806.^[89]

Bankruptcies and second marriage

Greenleaf's speculations ruptured his relationships with his family,^[68] most of whom he had persuaded to invest in his land speculations. It also left impoverished the family of William Cranch (who had married Greenleaf's sister) and many Bostonians.^[97] But by early 1795, Greenleaf had mended his personal relationship with his old business partner, James Watson, and with other business associates in New York City. He also was reconciled to his sister, Rebecca.^[98]

Having been ejected from Noah Webster's home, Greenleaf moved to Philadelphia^[98] (possibly because it was considered the halfway point between Washington 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.^[3][99] (Penn built a luxurious mansion on the estate about 1773, and died on February 9, 1795).^[100] Then on April 15, 1795, Greenleaf purchased General Philemon Dickinson's house on Chestnut Street in Philadelphia for $28,000. On an opposite corner was Robert Morris' home.^[101] Greenleaf gave lavish parties at both homes.^[24]

Bankruptcies

Greenleaf did not live long in Philadelphia. Lansdowne was seized by the county sheriff for nonpayment of debts some time during 1797, and sold at auction for $55,100. Dickinson foreclosed on Greenleaf's other home for nonpayment of the mortgage on November 29, 1797. (Dickinson repurchased his home at auction for $15,733.)^[102]

By late 1797, Greenleaf was on the verge of bankruptcy. But there was no national bankruptcy law; Congress would not pass one until the Bankruptcy Act of 1800.^[103] Greenleaf was therefore 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 discharged 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.^[104]

Second marriage

While Greenleaf was in bankruptcy court, he married Ann Penn Allen (nicknamed "Nancy") on April 26, 1800.^[94] Allen was known to Greenleaf as early as 1795 (Thomas Law mentioned her in a letter about Greenleaf that year).^[105] She came from a wealthy and famous family: Her father was James Allen, a prominent businessman and political figure in Allentown, Pennsylvania. 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).^[2]

Ann was also heir to her father's large estate.^[24] To protect herself from Greenleaf's creditors, Ann established a trust for all her property before her marriage. William Tilghman (who in 1805 would become Chief Justice of the Supreme Court of Pennsylvania) and John Lawrence were appointed the trustees.^[3]

Life in Allentown

After their marriage, Greenleaf and his wife divided their time between homes in Allentown and Philadelphia.^[24] In 1802, Ann gave birth to a daughter, Mary Livingston Greenleaf. Mary married her cousin, the merchant Walter C. Livingston of New York (son of Henry W. Livingston), on July 28, 1828. A second daughter, Margaret Tilghman Greenleaf, was born the following year. Margaret married Charles Augustus Dale of Allentown in July 1832.^[3] Mary had eight children, but only one of them married (and this daughter had no children of her own).^[106] 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.^[107]

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.^[107] A replica by Gilbert Stuart of the Lansdowne portrait of George Washington hung in the mansion.^[108] Although Greenleaf lived comfortably on his wife's income, in 1810^[12] he purchased small amounts of land in and around the city, subdivided it, developed it, and sold it. Because of this development, many of the streets in Allentown bear the names of Greenleaf's relatives and associates: Law, Livingston, Morris, Pratt, Priscilla, Tilghman, and Webster.^[108] Greenleaf also helped promoted the construction of a bridge across the Lehigh River.^[24]

From 1807 to 1828, Greenleaf listed his primary residence as Philadelphia.^[108] Although he continued to reside in Allentown until 1826,^[108] Greenleaf spent most of his time in Philadelphia.^[24]

Washington, D.C., continued to draw Greenleaf. Greenleaf spent much of the last 40 years of his life defending himself from lawsuits,^[109] and he returned to Washington regularly to defend himself in these cases.^[24] Greenleaf made his first trip back to Washington on August 17, 1799, and returned repeatedly to the city between 1800 and 1828. He usually stayed two weeks, advertising in the National Intelligencer his arrivals and departures. He usually stayed at either Davis' Hotel on Pennsylvania Avenue NW, Captain Wharton's boarding house on F Street NW, or Miss Heyer's boarding house on New Jersey Avenue SE (near Thomas Law's home).^[108]

Return to Washington and death

As early as 1816 or 1817, James Greenleaf made known to his wife his desire to return to Washington, D.C., to live full-time. Ann Greenleaf, however, was unwilling to do so. 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."^[24] Nonetheless, Ann accompanied her husband to the District of Columbia for short periods. They spent Christmas 1821 in the city, and during the winter of 1826 they rented a home (owned by William H. Crawford) on 14th Street NW just north of Thomas Circle. They also spent the summer of 1828 in the city, living at Washington House at 222 North Capitol Street.^[108] During the first two decades of the new century, Greenleaf continued to repair many of his personal relationships. By 1830, he had reconciled with most of his family. He spent Christmas 1830 at the Washington home of his brother-in-law, William Cranch. During this stay, he also reunited with Noah Webster for the first time in years.^[110]

Although he was not estranged from his wife,^[111] James Greenleaf moved permanently to Washington in 1831. For the remainder of his life, he listed his primary residence as Washington, while Ann continued to live in the mansion in Allentown.^[3] In 1831 (or shortly before), Greenleaf constructed a two-story wooden house on the corner of 1st and C Streets NE (lots 17 and 18)—just around the corner from William Cranch's home. His property included a stable with two horses and some cows. He grew mulberry trees, a widower acted as his housekeeper and cook, and her son-in-law worked as his gardener. Greenleaf also owned a small farm of perhaps an acre or less situated at 6th Street and Virginia Avenue SW. (The site was later the location of the Jefferson School, designed by noted local architect Adolf Cluss). The house sheltered Major General William Tecumseh Sherman and some of his officers after the Second Battle of Bull Run in 1862. It was razed around 1870.^[111][112]

The final years of Greenleaf's life were spent quietly. His few financial needs were met by his wife and by speaking fees. He had almost no debts by the late 1830s, but retained extensive land holdings (although little of it was developed).^[113] He associated with childhood friends John Quincy Adams, Judge William Cranch, and Cranch's wife Nancy (Greenleaf's sister), and attended the Unitarian Church.^[111] He otherwise had few friends and did not socialize much, preferring to spend most of his time sleeping, eating, and reading in the library on the ground floor of his home. He continued, however, to make the occasional visit to Allentown to see his wife.^[24] In the final few years of his life, his assistant was Bushrod Robinson—later a lieutenant in the Union Army, an important local businessman, and famous socialite in Washington. At the time he knew Greenleaf, Robinson was still in his early 20s. He described Greenleaf as 5 feet 7 inches (1.70 m) tall, about 140 pounds (64 kg), blond haired, clean shaven, courteous, and a great lover of children and books.^[114] (Greenleaf owned 2,612 books, which was an extremely large library for the day.)^[113]

Death

Around the first of September 1843, Greenleaf fell ill. His health did not decline too much, however, and the illness seemed minor.^[115] Greenleaf's sister, Nancy Cranch, died on September 16, 1843. After learning of her death late in the evening, Greenleaf went into shock.^[24] Greenleaf's health deteriorated rapidly over the next few hours, and he died in the early morning hours of September 17.^[115]

James Greenleaf was interred in Congressional Cemetery in Washington, D.C.^[3][24]

Ann Greenleaf continued to live in her Allentown mansion for the next eight years. Blind in the last few years of her life,^[116] she died in Allentown on September 21, 1851.^[3] She was originally buried in the family vault in the Christ Church cemetery in Allentown.^[117] Her remains were later removed to North Laurel Hill Cemetery in Philadelphia.^[116]

Resolution of the North American Land Company

The North American Land Company stayed in existence until 1872.^[89]

Morris and Nicholson honestly believed that, if their cash flow problems were fixed, they could make payments on the property they owned and their shares would be returned to them. This proved incorrect. On October 23, 1807, all stock in the company was sold at 7 cents on the dollar to the 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.^[93]

From 1797 to 1843, James Greenleaf was a party, plaintiff, or defendant in six lawsuits which went all the way to the Supreme Court of the United States. He successfully defended himself all six. In another seven suits regarding the Aggregate Fund which also went to the Supreme Court, he was either completely or partially successful.^[109] The Supreme Court cases which name James Greenleaf directly are:

• Knox v. Greenleaf, 4 U.S. 360 (1802)
• O'Neale v. Thornton, 10 U.S. 53 (1810)
• Fletcher v. Peck, 10 U.S. 87 (1810)
• Pratt and Others v. Carroll, 12 U.S. 471 (1814)^[118]
• 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)

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 the District of Columbia. The case discusses Greenleaf, Nicholson, and Morris' involvement in selling lots on Water Street.

Legacy

Greenleaf Point in Washington, D.C., is named for James Greenleaf.^[2][119] 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.^[120] 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.^[121] Twenty half-finished structures, begun by Greenleaf, clustered around high land on South Capitol Street.^[122] The city's first Methodist church meeting was held in one of the "20 Buildings" in 1802.^[123] By 1824, however, the 20 Buildings were in ruins.^[124]

Another historic structure erect by Greenleaf was the Thomas Law House, built in 1795.^[125] This structure still stands in 2012, and is listed on the National Register of Historic Places.

Greenleaf also at one time owned the land on which the Washington Arsenal and the District of Columbia Penitentiary were later built.^[2] This was the site where George Atzerodt, David Herold, Lewis Powell, and Mary Surratt were hanged on July 7, 1865, for their role in assassinating President Abraham Lincoln. Both sites are now part of Fort Lesley J. McNair.

Greenleaf School, a former D.C. public school located on 4th Street SW between M and N Streets SW, was accidentally named for James Greenleaf.^[126] 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.^[127] That building was replaced in 1896 and sometime by 1911 the school name was mistakenly attributed to James Greenleaf. The school itself 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.^[128] 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.^[129]

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."^[130]

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