Stonewall and the Chindit I: On Character and Generalship

Contemporaries of British Major General Orde Charles Wingate, famed leader of the Chindit special forces in Burma and a noted guerrilla commander in Africa and Palestine before that, often searched for someone with which to compare him. They Thomas J. "Stonewall" Jacksonusually hit upon Chinese Gordon, Lawrence of Arabia, and . . . Stonewall Jackson. Wingate himself largely rejected the first two, but the third fit rather well. It still fits the best of all.


Thomas J. “Stonewall” Jackson (1824-1863) is well known to readers of Emerging Civil War for his exploits as a Confederate commander in Virginia from Manassas in 1861 to his mortal wounding at Chancellorsville in May 1863. Orde Wingate (1903-1944) is probably less known. He achieved infamy and fame fighting Arabs in Palestine in the late 1930s, later leading Anglo-Ethiopian forces into Addis Ababa against the Italians in 1941. His best-known achievement was his pioneering of what he called “Long Range Penetration” units (nicknamed Chindits) in Burma from 1943 until his death in an air crash in March 1944.

Outwardly, both Jackson and Wingate were very similar men – almost intentional close copies in some ways. Both came up through the artillery. Both held high command at a time when their successes were rays of hope in otherwise dark national pictures, used smaller forces to defeat larger enemy units, and were known for their daring and skill at maneuver.

In personality and outlook, both Jackson and Wingate showed strikingly similar tendencies. Both devoted to their wives, they each left a young child behind at their death –  Jackson’s daughter Anna was less than 1 in 1863, Wingate’s son Orde Jonathan was born 3 months after Wingate’s death in 1944. Both were deeply religious, subscribing to fundamentalist doctrines; indeed, neither man’s outlook, concept of war, or personality can be fully understood without taking their religion into account. For them, the world was black and white, and they were on the side of right – perspectives that strained relationships with superiors and subordinates alike. Each drove their men hard and themselves just as hard, sometimes to the detriment of their health.

Stonewall Jackson and Orde Wingate were also some of the greatest eccentrics American military history has ever encountered. Jackson sucked lemons, kept his hand in the air to balance his body, and avoided pepper. He famously almost never changed clothes, to the point where a new uniform on the eve of the Battle of Fredericksburg was cause for celebration. Wingate shared this latter trait with Jackson, famously showing up to a high-level strategy conference in Canada wearing the same stained uniform he used in the Burma jungle. He also would receive visitors naked, regularly ate onions because of their supposed curative properties, and ordered his officers to always move at a run.

None of this would have made either man much more than an object of derision; indeed, contemporaries of both questioned their sanity on more than one occasion. But they both possessed a will to win, a will to seize the objective, and a determination to see their operations through that carried down to the enlisted men and infused their units with a very high esprit d’corps. This translated to success on the battlefield.

To be sure, there were important differences between Stonewall Jackson and Orde Wingate, beyond simply time and national origin. Jackson was senior (Lieutenant General to Major General) and commanded more men (30,000 at peak to 15,000 for Wingate). Jackson spent most of his life in North America, while Wingate was born in India, grew up in Britain, and later served in the Middle East, Asia, and Africa. Wingate was also a failed suicide.

Nonetheless, these two men became two of the great subjects for biographers after their deaths. The discussion about each one continues, and shows no sign of abating. Why are these men such objects of interest and fascination?

Top: Stonewall Jackson in April 1863

Bottom: Orde Wingate in 1944


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