James Henry Dooley (17 January 1841–16 November 1922), attorney, financier, and philanthropist, was born in Richmond and was the son of Irish immigrants, John Dooley, a hat manufacturer, and Sarah Dooley. During the Civil War his younger brother, John Edward Dooley, kept a candid diary that was later published. James H. Dooley was educated in two of Richmond's premier boys' schools and entered Georgetown College (later University), in Washington, D.C., in September 1856. He graduated in 1860 and received a master's degree in 1865. Having enlisted as a private in the 1st Regiment Virginia Infantry on 5 April 1862, he was wounded and taken prisoner at Williamsburg on 5 May. After being exchanged and given a medical discharge on 17 October, Dooley served as a noncombatant lieutenant in the Confederate ordnance corps. He qualified to practice law before the Richmond court in November 1865. On 11 September 1869 in Staunton, Dooley married Sarah "Sallie" O. May. They had no children.
Dooley began a general law practice and won renown for his defense of an innocent man accused of murder. Elected to the House of Delegates in 1871 for the first of three consecutive two-year terms representing the city of Richmond, he served on the Committee on Militia and Police during his first two terms. He sat on the Committee for Courts of Justice during all three assemblies and was ranking member during his second and third terms. Dooley rapidly rose to prominence as a member of the Conservative Party majority and was ranking member of the influential Committee on Rules in his second and third terms. He also chaired the Committee on Propositions and Grievances during his final term in the House. While in the General Assembly, Dooley advocated paying off the full principal of the accumulated public debt with interest, and he supported bills to facilitate construction by the Chesapeake and Ohio Railroad Company. He did not seek reelection in 1877.
Dooley helped found the Commercial Fire Insurance Company of Richmond in 1875 and became its vice president. His knowledge of insurance and banking gained him seats on the boards of several other Virginia and national insurance companies, including Merchants and Mechanics Insurance Company of Virginia, the Petersburg Savings and Insurance Company, and the Continental Insurance Company of Chicago and New York. A respected student of finance, Dooley served on the boards of the Merchants National Bank, in Richmond; the Old Dominion Trust Company; and the Richmond Trust and Safe Deposit Company, of which he was a vice president.
In 1880 Dooley, Joseph Bryan (1845–1908), and Thomas Muldrup Logan joined Philadelphia ship-owners Thomas and William Clyde in acquiring controlling interest in the Richmond and Danville Railroad Company, and establishing the Richmond and West Point Terminal Railway and Warehouse Company, a railroad holding company. The Terminal, as it was called, made extending the Richmond and Danville into other southern states possible. It became the centerpiece of a 9,000-mile network of railroads and steamship companies as far as the Texas border. Dooley sat on the Richmond and Danville board and served as its vice president and associate counsel. In the 1890s Dooley joined the Richmond banker John Skelton Williams in transforming the Seaboard Air Line Railway into a trunk line connecting Richmond with Tampa, Florida. Dooley served as a director of the Seaboard, and in 1909 was elected to the board of the Chesapeake and Ohio Railway Company.
During the 1880s Dooley and his associates purchased a controlling interest in the Sloss Iron and Steel Company (later the Sloss-Sheffield Steel and Iron Company). He also served as president of real estate development companies in Virginia, Alabama, and Minnesota. Dooley was also one of several investors who purchased the patent for the telautograph, a forerunner of the modern fax machine that revolutionized the communications industry by allowing electronic transmission of handwriting and line drawings. In 1888 Dooley and his associates chartered the Gray National Telautograph Company, with headquarters in Richmond.
By the mid-1880s Dooley had become a respected financier. He lectured and published occasional essays on economic and political issues in Richmond newspapers and in pamphlets. Between 1886 and 1893, Dooley and his wife constructed and elegantly furnished a large Richardsonian Romanesque Revival mansion overlooking the James River just west of Richmond, where they created an arboretum, and Italian and Japanese gardens on the hundred-acre Maymont estate. In the 1910s they also built a palatial Italianate marble summer house, Swannanoa, on Afton Mountain, near Waynesboro.
Following his father's death in February 1868 Dooley became known as Major Dooley. While his father had earned the title on the battlefield, the younger Dooley carefully reminded others that he served as a private during the Civil War. An avid supporter of improving Virginia's public schools, Dooley served for many years as an officer of the Co-Operative Education Association of Virginia. He sat on the board of the Medical College of Virginia and was president of the Art Club of Richmond. Dooley was particularly generous to institutions that helped children. Beginning in 1916 he gave more than $50,000 to help build and equip a children's hospital that bore his name at the Medical College of Virginia, and he bequeathed $3 million to Saint Joseph's Academy and Orphan Asylum (later Saint Joseph's Villa), believed at the time to be the largest private bequest to a Catholic institution in the country. In 1920 Georgetown College recognized his lengthy legal career and community service by awarding him an honorary doctorate of laws.
James Henry Dooley numbered among the wealthiest men in Virginia; his estate was valued at between $5.5 and $6 million. He died in a Richmond hospital on 16 November 1922 and was interred in a vault at Hollywood Cemetery until March 1924, when his remains were re-interred in a newly completed mausoleum at Maymont. Swannanoa and Maymont were added to the Virginia Landmarks Register and the National Register of Historic Places in 1969 and 1971, respectively.
Biographies in Mary Lynn Bayliss, The Dooleys of Richmond: An Irish Immigrant Family in the Old and New South (2017), Catholic Virginian 7 (Nov. 1931): 15, 38–39, and Charles M. Caravati, Major Dooley (1978), with portrait on iii, and Dale Cyrus Wheary, Maymont: An American Estate (2015); Dooley family papers, Maymont House Museum Archives, Maymont Foundation, Richmond, Va.; Dooley correspondence and some business records in Branch and Company Papers, Virginia Historical Society, Richmond, Va.; Compiled Service Records of Confederate Soldiers (1861–1865), War Department Collection of Confederate Records, Record Group 109, National Archives and Records Administration, Washington, D.C.; State Corporation Commission Charter Books, Record Group 112, Library of Virginia (LVA); Richmond Daily Whig, 15 Sept. 1869; W. David Lewis, Sloss Furnaces and the Rise of the Birmingham District: An Industrial Epic (1994); Maury Klein, The Great Richmond Terminal: A Study in Businessmen and Business Strategy (1970); Richard E. Prince, Seaboard Air Line Railway: Steam Boats, Locomotives, and History (1969); Marriage Register, Staunton, and Death Certificate, Richmond City (with birth date), both in Bureau of Vital Statistics, Commonwealth of Virginia Department of Health, Record Group 36, LVA; bequests reported in Richmond News Leader, 27 Nov. 1922 (with text of will); obituaries in Richmond News Leader and Richmond Times-Dispatch, both 17 Nov. 1922; editorial tributes in Richmond News Leader, 27 Nov. 1922, and Richmond Times-Dispatch, 28 Nov. 1922; memorial by John Stewart Bryan in Virginia State Bar Association Proceedings (1923), 63–65.
Written for the Dictionary of Virginia Biography by Mary Lynn Bayliss.
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>Mary Lynn Bayliss,"James Henry Dooley (1841–1922)," Dictionary of Virginia Biography, Library of Virginia (1998– ), published 2017 (http://www.lva.virginia.gov/public/dvb/bio.asp?b=Dooley_James_Henry, accessed [today's date]).
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