Wise to stand guard at the hanging of John Brown at Harper's Ferry in 1859 under the command of VMI Majors William Gilham and Thomas J.
[3] Gregory became a prominent attorney, businessman and land developer in Richmond, Virginia, where he was an officer of Guaranty Trust Company, a predecessor of the modern Bank of America.
They made their home at "Granite Hall", which was located near the south side of the James River in Chesterfield County, Virginia, where he had a large mansion erected.
[5] Reverend Meeks held the first gay marriage ceremony in Virginia, on the lawn of St. Peter's Church in Richmond, in August 1978.
[6] In 1979, while serving on Richmond'’s Human Relations Commission, Gregory became a big proponent, albeit unsuccessfully, of adding sexual orientation to the city code's nondiscrimination policies.
Gregory was also involved in a scheme to extend streetcar service from Westhampton Lake (now part of the campus of the University of Richmond) across the Westham Bridge to the suburban resort community of Bon Air.
The land surrounding the Gregory family estate, Granite Hall, became the site of a golf course of the Bon Air Country Club after World War II, and a subdivision beginning in 1958.