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.

[3] 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.

[9] 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.

[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.

[13][20] 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.

[25] 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.

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.

Greenleaf first approached his existing business partner, James Watson, with an offer to finance the purchase of the lots and the construction on them.

[11] But when Appleton fell ill in September 1794, Greenleaf summoned his brother-in-law and friend William Cranch to Washington, D.C., to act as his sales agent.

[46][47] 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 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.

[60] 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.

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.

[22][67] 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.

[68] Many European companies and individuals which owed Morris money had declared bankruptcy, leaving Greenleaf with severe cash flow challenges.

[74] 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.

[81] 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.

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.

For the remainder of his life, he listed his primary residence as Washington, D.C., while Ann continued to live in the couple's mansion in Allentown.

The site was later the location of the Jefferson School, designed by local architect Adolf Cluss, and sheltered Major General William Tecumseh Sherman and some of his officers after the Second Battle of Bull Run in 1862.

[93] 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.

[22] In the final few years of his life, Greenleaf's assistant was Bushrod Robinson, later a lieutenant in the Union Army and a local businessman and Washington, D.C., socialite.

Robinson 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.

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.

[108] Having been ejected from Noah Webster's home, Greenleaf moved to Philadelphia[108] possibly because it was considered the halfway point between Washington, D.C., and New York City.

[110] 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.

[91] Although Greenleaf lived comfortably on his wife's income, in 1810[11] 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.

[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.