| Name |
Class year |
Notability |
References |
| Smith, Francis HenneyFrancis Henney Smith |
1833 |
Major General of Virginia Cadets and Colonel in the Virginia Militia; first and longest serving superintendent of Virginia Military Institute (1839–1889) |
|
| Hill, Daniel HarveyDaniel Harvey Hill |
1842 |
Lieutenant General in Confederate States Army; professor at Washington and Lee University and Davidson College; later the first president of the University of Arkansas (1877–1884) |
|
| Lee, George Washington CustisGeorge Washington Custis Lee |
1854 |
First Lieutenant US Army, Major General CSA; graduated first in his class at the Academy; father Robert E. Lee, class of 1829, graduated second in his class; President, Washington and Lee University (1871–1897) |
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| Webb, Alexander S.Alexander S. Webb |
1855 |
Major General; recipient of the Medal of Honor for his actions at the Battle of Gettysburg for personal bravery and leadership repulsing Pickett's Charge; president of the City College of New York (1869–1902) |
|
| Chaplin, Winfield ScottWinfield Scott Chaplin |
1870 |
Chancellor of Washington University in St. Louis (1891–1907), Dean of the Lawrence Scientific School at Harvard University. Faculty member at Maine State College, Imperial University in Tokyo, and Union College. |
|
| Mearsheimer, JohnJohn Mearsheimer |
1970 |
Served five years as an Air Force officer; political science professor at University of Chicago (1982–present); proponent of offensive realism |
|