[2] A successful planter, capitalist, banker, director, and early Thoroughbred breeder/importer, he was considered the "wealthiest man of his day".

"He succeeded to the largest estate in Virginia"[8] upon his return to the United States in 1790; as he was the only surviving son after his father's death in 1779.

[9] In addition to shipbuilding at Neabsco Iron Works, Tayloe had other dealings in Prince William County, Virginia.

He served as a county postmaster for a time, and his stagecoach lines stopped in Occoquan, giving passengers a chance to disembark here.

On March 25, 1812, at the Davis Hotel, he founded "The Produce Bank of the Potomac" with again John Van Ness, Charles Carroll of Bellevue, Elias B. Caldwell, Tench Ringgold, C.W.

On the breaking out of the War of 1812, Tayloe was made lieutenant colonel of the cavalry of the District of Columbia and saw active service.

[17] "Another invitation recalls one of General Washington's closest friends, whom he persuaded to become a resident of Washington in its infancy, and who built the spacious mansion on the corner of New York Ave and Eighteenth Street, which is one of the surviving relics of the primitive city, not having been destroyed by the British in 1814 - Col. Tayloe: "Mr. Tayloe requests the favor of Mr. Van Rensselaer to dine with him on Sat next at 4 o'clock.

[19] His son, Henry Augustine Tayloe, founded the Fair Grounds Race Course in New Orleans with Bernard de Marigny in 1838.

Like his father, John Tayloe III was a successful horseman, and was one of the first breeders to import Thoroughbred foundation stock to the United States from England in the 1780s, keeping some at the Belair Stud.

The inaugural match featured John Tayloe III's Lamplighter and Gen. Charles Carnan Ridgely's Cincinnatus, for 500 guineas, ran in 4-mile heats, and won by the former, a son of Imp English bred stallion Medley.

[21] The site of today's Eisenhower Executive Office Building, this first course's history was short lived as it stood in the path of L'Enfant's city plan.

In 1802 the Club sought a new site for the tract, as the current one that lay the rear of what is now the site of Decatur House at H Street and Jackson Place, crossing Seventeenth Street and Pennsylvania Avenue to Twentieth Street-today the Eisenhower Executive Office Building-was being overtaken be the growth of the Federal City.

P. Custis, John Threlkeld of Georgetown and George Calvert of Riversdale, Bladensburg, Maryland, the contests were moved to Meridian Hill, south of Columbia Road between Fourteenth and Sixteenth Streets, and were conducted at the Holmstead Farm's one-mile oval track.

The Tayloes raised a family of 15 children:[12] sons Benjamin, Edward, Charles, William Henry, John, Henry Augustine, George, Lloyd, Robert Carter; daughters Henrietta, Catherine, Rebecca, Ann, Virginia, Ann Ogle, Elizabeth.

His wife was esteemed for sincerity and kindness of heart, graceful and dignified manners, and true and unaffected piety."