Born a slave in Thomasville, Georgia, Henry O. Flipper (1856 – 1940) was the first African-American graduate of the United States Military Academy at West Point in 1877, earning a commission as a 2nd Lieutenant. 
Flipper’s owner lost his slaves in a bitter divorce to his wife, who took them to Atlanta and allowed them to be educated in blatant defiance of Georgia law. Influenced by his contact with Union soldiers during Sherman’s march through Atlanta, Flipper applied to West Point. 
After easily passing academic and physical examinations, that eliminated most black and white nominees, 17-year old Flipper officially became a cadet on July 1, 1873. Despite hazing, isolation, and general maltreatment, Flipper graduated 50th out of a class of 76, on June 4, 1877.
He served four years as a cavalry officer in the West, before being court-martialed and discharged for “conduct unbecoming an officer and a gentleman” (code for being an uppity nigger and keeping company with a white woman) in 1882. He spent the rest of his life trying to clear his name. 
In December 1976, four decades after his death, the U.S. Army granted Flipper an honorable discharge, dated June 30, 1882. A ceremony was held at West Point, where a bust was unveiled in his honor. President Clinton pardoned Lt. Flipper in February 1999.

Reginald F. Lewis (December 7, 1942 – January 19, 1993) was a Harvard educated Wall Street lawyer, financier, and philanthropist. He was the first African American to own a billion dollar company, with his 1987 leveraged buyout (LBO) of Beatrice Foods. In 1996, TLC Beatrice International had sales of $2.2 billion, ranking number 512 on the Fortune 1000 list of largest companies. Lewis chronicled... his exploits in the biography “Why Should White Guys Have All the Fun”.

Born in Baltimore, Maryland, Lewis earned a football scholarship to Virginia State College, graduating in 1965 with a degree in Economics. He graduated from Harvard Law School in 1968. After 15 years as a corporate lawyer, Lewis started the venture capital firm TLC Group LP in 1983. His first major deal was McCall Pattern Company in 1983, for $22.5 million. He later sold McCall for $90 million. After paying investors, his personal profit was $73.5 million.

In 1992, Forbes listed Lewis among the 400 richest Americas, with an estimated net worth of $400 million