Maj. Gen. Sinclair Whittier, CSA

The commanding officer of the Richmond Special Legionnaires


b: May 17, 1839, Richmond, VA
d: February 10, 1911, Fire Island, NY

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Son of Phillip Whittier and Antonia Pendelton Whittier, Sinclair Whittier was descended from two prominent Richmond families.  His Virginia pedigree traces back to some of the earliest English settlers of the area; counted amongst his ancestors are William Byrd II, founder of the city of Richmond, and Francis Lightfoot Lee, signer of the Declaration of Independence.

William Byrd II and Francis Lightfoot Lee, Whittier’s (possibly gay?) ancestors

Whittier’s maternal grandfather, John Pendleton, claimed to have fought in the War of 1812, and his father and older brothers, Gerard and Paul, fought in the Mexican-American War.  With this auspicious background to live up to, it is no wonder that at an early age Whittier decided to pursue a military career.

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Whittier as a West Point cadet

transparentspacerAfter having brandished a toy sword for years, in 1856 he finally became a cadet at the US Military Academy at West Point.  It was here that he first entered into his tumultuous relationship Jonathan Franklin Hale, future commander of the 13th Rhode Island Infantry.Upon graduation from West Point in 1860, Whittier was stationed at Fort McHenry in Baltimore.

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With the outbreak of the Civil War, Whittier, like many of his Southern compatriots, resigned his commission with the US Army in order to fight for his home state of Virginia.  With the help of his family connections he was able to raise a regiment and secure a place as a Colonel in the Confederate Army.  Between June of 1861 and September of 1862 he took part in the battles of Big Bethel, 1st Bull Run, Dranesville, Kernstown, Crosskeys, and Chantilly.  In January of 1863 he was suddenly promoted to Major General (skipping several ranks) and placed in command of the Richmond Special Legionnaires, a specially formed secret force tasked with preparing a sneak attack on Washington.

Sinclair Whittier and a "friend", shortly before Whittier's promotion to Maj. General

Whittier and a “friend”, shortly before Whittier’s promotion to Maj. General

This came as somewhat of a surprise, as during his career prior to this Whittier had not particularly distinguished himself, nor was there anything obvious in his curriculum vitae recommending him for such an important duty.

It is conjectured that either his family pulled some strings to secure him the post, or that Whittier possessed certain, less obvious, qualities that made him ideal for the job.  In either case, by the beginning of February he had retired with his new army to a secret camp in the Shenandoah Valley.  In late June, after many months of training during which Whittier found himself less and less satisfied with his supposedly enviable commission, the R.S.L. were finally deployed with instructions to launch against Washington via Pussy Willow Gap.  It was there, along a creek baring that same name, that Whittier would suffer a most humiliating defeat at the hands of his former West Point classmate, Jonathan Franklin Hale.

Watch an interview with historian Natalie Molyneux on the choice of Whittier as RSL commander.

Watch an excerpt featuring Whittier’s unsent letter to Hale announcing his promotion to Major General .

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