In the 1780's, Monroe purchased land patents in 100,000 acres of land, primarily located in Fayette and Lincoln County areas of the Kentucky territory, which was then a part of Virginia. He had planned a joint purchase with James Madison of additional lands patents in the Genesee Valley in New York, but was forced to withdraw from that deal in 1785 due to a shortage of liquidity (Ammon 1971: 38-39, 78).

Monroe also received land grants for 5,333 1/3 acres in Kentucky as a result of his service in the military during the Revolutionary War. This was awarded in Land Bounty Warrant No. 2368 on February 2, 1784, to Monroe for his service as a Major in the Virginia Continental Army for a term of three years (Wilson 1953: 50).

Historians often state that Monroe was the last President of the United States who had fought in the Revolutionary War, and they refer to him as the "last of the cocked hats." However, some sources show that Andrew Jackson, a later President, also fought in the Revolution, even though he was an under-age teenager at the time.

Monroe joined the Third Virginia Infantry at the age of 18, in 1776, leaving his studies at the College of William and Mary. He fought with General George Washington, and was wounded in the famous attack on the Hessian forces at Trenton, New Jersey in December 1776. Monroe had attained the rank of Major, and was later commissioned as a Lieutenant Colonel by the Virginia legislature, a promotion endorsed by General Washington (Cunningham 1996: 1). His rank at the time relevant to the award of a land bounty by the Virginia legislature was that of a Major. Such officers typically received grants of 4,000 to 5,333 acres, while other ranks received higher or lower amounts. For example, Lieutenant Colonels received anywhere in the range from 4,500 to 6,666 acres, and Colonels 5,000 to 8,888 acres (Wilson 1953: 2).

Monroe would use a portion of the Kentucky land holdings as payment to George Nicholas in 1788 or 1789 for purchase of the 800-acre "Monroe Hill" tract and nearby town lots in Charlottesville. Some portion of the Kentucky lands were thus transferred to Nicholas as the equivalent of the purchase price was 2,500 pounds (Ammons 1971: 74, citing 1788 and 1789 correspondence of Monroe; Deed Book 10, pages 188-89). Other efforts in 1794 through 1796 by Monroe's uncle, Joseph Jones, to find purchasers willing to pay the prices sought by Monroe for portions of the Kentucky land proved unsuccessful (Ammon 1971: 116).

Monroe continued his acquisitions and sales of Kentucky land in the 1790's, often in coordination with his uncle Joseph Jones, believing that "'the profit [would] be immense, for be assured land there will soon rise greatly'" (Gawalt 1993: 257, quoting Monroe correspondence to Jones). He would later purchase and promptly resell 14,720 acres in of Kentucky land, exercise options on an additional 15,000 acres in the Licking Creek area, and purchase and sell a tract of 20,000 acres in the Clay County area of Kentucky (Gawalt 1993: 258, 260).

Aside from his personal investments in property in such territories, Monroe's service as a diplomatic officer for the United States government was instrumental to the purchase of the Louisiana and Florida territories from the French and Spanish. To see the effect of these purchases by the U.S., click here to see maps of the developments of boundaries of the states and territories over time. Then click on the "back" button on your browser to return to this Ash Lawn-Highland web site.

Last Modified: September 2, 2012