Born: 1789-XX-XX Scotland, United Kingdom
Died: 1842-09-03 Philadelphia, Pennsylvania
Reeside moved with his parents shortly after his birth to Baltimore County, Maryland. Due to his family's limited resources, Reeside received limited formal education. Before the War of 1812, he began his professional career as a waggoner transporting merchandise between Baltimore, Philadelphia, and Pittsburgh. He later hauled goods in Ohio between Columbus and Zanesville. He eventually bought his own teams of horses, and obtained a contract with the U.S. Army to haul artillery. During the War of 1812, Reeside received a commission as forage master for troops under the command of General Winfield Scott. At the Battle of Lundy's Lane, he fought alongside the troops he supplied. After the war, he entered into the stagecoach business, operating a line from Hagerstown, Maryland to McConnellstown, Pennsylvania. He also won his first government mail contract. In 1818, he helped establish the first mail route along the Cumberland Road between Baltimore and Washington, DC. He moved to Cumberland, Maryland, where he managed his mail and stage lines and operated a tavern. In 1820, he sold the tavern to concentrate on expanding his stage and mail lines. In 1827, he moved to Philadelphia to manage mail service between Philadelphia and New York City. Over the next several years, he expanded his stage and mail lines, becoming the largest mail contractor in the country, with over 400 employees and 1,000 horses, earning him the nickname "Land Admiral."
During the administration of Andrew Jackson, Reeside became embroiled in a financial scandal, largely due to the malfeasance of Postmaster General William T. Barry. Barry was incompetent, and the Post Office suffered under his stewardship, but President Jackson retained him due to his loyalty to the administration, particularly during the scandal over John H. Eaton and his wife, Peggy O’Neill Timberlake Eaton. On March 29, 1834, the Senate adopted a resolution calling on the Committee on Post Offices and Post Roads to investigate conditions in the Post Office. On June 9, the committee reported, among other things, that the department was insolvent to the amount of $803,625; that Barry had borrowed large sums of money without authorization; and that he had eschewed competitive bidding in granting mail contracts, assigning many to political allies of the administration. Reeside raised money to help Barry, and he also lent him money from his personal funds. A legal battle ensued when Amos Kendall, Barry's successor, refused to repay Reeside. Reeside sued the U.S. Government for repayment, and in 1841, a jury awarded him approximately $190,000 in compensation. The legal battle continued, however, delaying repayment of the debt until 1857. When his mail contract ended in 1836, Reeside left the mail delivery business. He returned to his stage line business, purchasing a line on the Cumberland Road from Cumberland, Maryland to Wheeling, Virginia. In 1839, he sought all his interest in the Cumberland Road lines to concentrate on his suit with the government. He died shortly thereafter.
U.S. Senate Journal. 1833. 23rd Congress, 1st sess., 199; U.S. Senate Register of Debates. 1834. 23rd Congress, 1st sess., Appendix, 215-29; Pamela Baker, "Reeside, James," American National Biography, ed. by John A. Garraty and Mark C. Carnes (New York: Oxford University Press, 1999), 18:288-89; Robert V. Remini, Andrew Jackson and the Course of American Democracy, 1833-1845 Volume III (New York: Harper & Row, 1984), 175, 241-42.