Wingate’s Way – Leadership Lessons From Britain’s Maverick General Still Ring True Today

Orde Wingate reviews his troops during the battle of Ethiopia. (Image source: WikiCommons)

Orde Wingate (foreground) during the Ethiopia campaign of 1940-41. (Image source: WikiCommons)

“Orde Wingate’s experiences from World War Two offer lessons for 21st Century military planners, particularly in the areas of counter-insurgency, covert and special operations and proxy wars.”

Dr. Simon Anglim

MAJOR GENERAL Orde Wingate was the most controversial British commander of the Second World War, and can still split opinion even 70 years after his death.

This is unsurprising: a man who ate six raw onions per day, ordered all his officers to eat at least one themselves and who conducted press conferences in the nude while scrubbing himself with a wire brush is bound to leave an impression. However, much of the controversy runs deeper than this, stemming from his performance as military commander particularly in the years leading up do his death at the age of 41 in a plane crash in Burma in 1944.

Controversy surrounds his role during Palestine Arab Uprising of 1936-1939, when Wingate, a captain on the Staff of General Headquarters in Haifa, was ordered to train Jewish policemen, in British-organized counterterrorist units known as the Special Night Squads.

Wingate, a passionate Zionist, politicized this mission, turning it into the backbone of a personal campaign for a Jewish state. He deployed his Night Squads in politically explosive pre-emptive raids and reprisals against Arab villages believed to be hiding insurgents. He also used ‘robust’ interrogation methods to extract intelligence from prisoners.

Orde Charles Wingate (1903 to 1944). (Image source: WikiCommons)

Orde Charles Wingate’s role in the bloody suppression of the 1936-39 Arab Uprising remains controversial. Yet the lessons he learned in the dessert served the Allies well during the Burma campaign. (Image source: WikiCommons)

Despite this — or perhaps because of it — Wingate was summoned in late 1940 by General Sir Archibald Wavell, British commander-in-chief for the Middle East, to take over an operation organized by the MI(R) covert warfare branch of the British War Office aimed at escalating and steering guerrilla resistance in Italian occupied Ethiopia. Wingate succeeded far beyond MI(R)’s ambitions, raising and commanding ‘Gideon Force’, a purpose organized regular formation for operations deep inside hostile territory, which cooperated with local tribal irregulars in the Gojjam region of western Ethiopia to defeat an Italian force at least ten times its size. He also participated directly in restoring the Emperor Haile Selassie to the throne taken from him by the Italians five years before.

Yet he is best remembered in Britain for his command of the Long Range Penetration Groups in Japanese occupied Burma. These light infantry formations used ‘guerrilla’ methods. Supplied and supported by air, they conducted two major operations deep inside enemy territory: Operation Longcloth in 1943 and Operation Thursday in 1944.

These Long Range Penetration Groups are better remembered as the Chindits, a propaganda name derived from Wingate’s mispronunciation of Chinthey, the stone griffin figures which guard Buddhist temples in Southeast Asia. As part lion, part dragon, the Chinthey seemed an appropriate symbol for an air-land force, and their mythical significance to the people of the region was not lost on Wingate.

Wingate’s experiences in Burma and elsewhere are still relevant to this day, particularly in the light of likely future missions for the armed forces of many western democracies. His views on special operations, covert warfare, command and morale, among other things, speak to 21st Century militaries.

Wingate, an ardent Zionist, trained Special Night Squads to combat Arab guerrillas during the 1936 Palestinian Uprising. (Image source: WikiCommons)

Wingate, an ardent Zionist, trained Special Night Squads to combat Arab guerrillas (pictured here) during the 1936 Palestinian Uprising. (Image source: WikiCommons)

Wingate on Leadership

As a commander, Wingate embodied what could be described as the Sandhurst model of leadership — when a leader causes a group to perform a goal-related activity which the group would not have performed without the leader’s influence.

Moreover, in war, leaders also must think about their opponents’ likely goal-related activities and how best to thwart or disrupt them. An effective commander doesn’t just get his own soldiers to follow his will, but the enemy, too.

Indeed, Wingate was something of a pioneer of ‘effects-based operations’, a trendy buzzword for something that has actually been around for centuries. His first thought in any military scheme being the desired effect he wanted to have on the enemy. To the uninitiated this might seem ahead of its time, and while Wingate’s admirers claim he was a ‘military genius’, his papers suggest not so much a great original thinker than an astute cherry-picker and synthesizer of existing ideas who had no compunction about presenting them as his own.

However, where Wingate seems to have been original was in his view of what war and warfare actually were. And this brings us to his views on leadership. To Wingate, it was the hinge on which everything else swung. Because he saw war as a clash of cultures, dialectical and human-centred, people engaged in the fighting needed training, command and control and they also needed a degree of physical and mental conditioning.

A great deal of his approach to training was aimed not just at convincing the people under his command that they were actually capable of doing things they had previously thought impossible, but that they were better at it than others, especially the enemy. Subsequently, they would venture forth and demonstrate their prowess, not only to the enemy and third parties but to themselves as well.

Members of the British-trained Special Night Squad.

Members of the British-trained Special Night Squad.

Wingate on Training

Following from this, when faced with a military problem, Wingate’s aim seems to have been to turn what he saw as the typical British military virtues — fundamentally stronger self-discipline, and more aggression and initiative from all ranks — into tactical advantages by exploiting enemy weaknesses in these same areas. This seems to have started in Palestine, where Wingate believed that the superior discipline, initiative and skill at arms of British soldiers, the leadership and tactical nous of British officers and NCOs, and the high intelligence and enthusiasm of police volunteers, if tied to an efficient intelligence and information network, would allow them to defeat many times their own number of badly trained and poorly coordinated terrorists. This might point to a certain degree of elitism, but Wingate was convinced that the qualities he was looking for were innate in any British, Jewish or Ethiopian soldier; they just needed the right kind of training and indoctrination and the right kind of leadership to bring it out.

The Chindits were British and Indian special forces that waged a guerrilla-style war against the Japanese during the Bruma campaign. (Image source: WikiCommons)

The “Chindits” were a British and Indian special forces unit that waged a guerrilla-style war against the Japanese during the Bruma campaign. (Image source: WikiCommons)

Wingate on Special Ops

Wingate’s view was that guerrilla warfare and special operations was dependent on strong, pro-active leadership from the front even more than other forms of warfare. When GHQ Middle East was gathering arms and personnel for insertion into western and southern Ethiopia, Wingate argued consistently and vociferously for teams of trained guerrilla warfare specialists to be inserted into Italian-controlled territory. In his view, irregular and insurgent operations hinged on an activist minority, a ‘hard core’ of leaders, and British forces would prevail by providing or enhancing it. This ‘corps d’elite’ would be more effective than ‘peddlers of war material and cash’ because resistance depended upon appealing ‘to the better nature, not the worse.’

“We can hope that the rare occasional brave man will be stirred to come to us and risk his life to help our cause,” he wrote “All the rest, the rush of the tribesmen, the peasants with billhooks, is hugaboo.”

Orde Wingate was highly critical of T.E. Lawrence. (Image source: WikiCommons)

Orde Wingate was highly critical of T.E. Lawrence. (Image source: WikiCommons)

Wingate on T.E. Lawrence

In a paper he wrote after the Ethiopian operation, Wingate disparaged the methods of guerrilla warfare associated with his distant relative T.E. Lawrence, for whom he seems to have nursed a lifelong contempt, often using the words ‘Lawrence’ and ‘wrong’ as interchangeable.

In this particular paper, he contended that Lawrence’s method of guerrilla warfare, consisting essentially of handing out weapons and money to local irregulars or tribal warriors who would then fight the enemy on their own terms and under their own local chieftains, would not only be interpreted as a sign of British weakness, but would result in cash and guns being misappropriated for the guerrillas’ own ends.

He then outlined the ‘right’ method:

Hitherto we had made the mistake of appealing to the cupidity and self interest of the Ethiopians by offering them money and poor quality war material. These qualities were all on the side of the enemy. Courage, faith and self respect, these were the qualities we could appeal to successfully because they were on our side. We had first to convince the Ethiopian, suspicious as he was of all white men, of our bona fides. This meant he must see us fighting not by his side but in front of him. His contact with our young officers must convince him that…we were not only brave soldiers but devoted to the cause of his liberties…[C]ease trying to stimulate the revolt from without, using agents, but…enter amongst the patriots using small columns of the highest fighting quality, with first class equipment, to perform exploits and to teach self sacrifice and devotion by example instead of by precept. By doing so we should not only fan the revolt to proportions that really threatened the enemy’s main bases, but should also assume its direction and control a most important factor in any future settlement.

A Chindit column marches off into the jungles of Burma, 1943. (Image source: WikiCommons)

A Chindit column marches into the jungles of Burma, 1943. (Image source: WikiCommons)

Wingate on Morale

Alongside this was what Wingate saw as the basis of good morale and combat motivation: all the nice rations and hearts-and-minds public relations in the world are a waste of time and effort if your soldiers and their local allies don’t think that you are serious about the cause you are fighting for — and serious about winning.

Against what was seen widely as good practice at the time, Wingate believed intensely that the soldiers under his command, even the long-service professionals, should have some understanding of the political objectives for which they were fighting, something which was grasped also later on by field marshals Montgomery and Slim, but taken further by Wingate.

Chindits board an Allied C-47 in preparation for Operation Thursday. (Image source: WikiCommons)

Allied commandos board a C-47 in preparation for Operation Thursday. (Image source: WikiCommons)

Wingate on Winning Hearts and Minds

From the Ethiopia operation onwards, Wingate argued that penetration forces must have what he called a ‘doctrine.’ This meant the political ‘message’ that military action should send to allies and potential allies in enemy-occupied territory, that Allied forces were ‘on their side’.

‘The force must operate with a definite propaganda… or creed of war… based on truth, and not lies. Lies are for the enemy. The truth is for our friends.’

This ‘creed of war’ would shape the actions of penetration forces right down to the tactical level, including matters of planning, preparation, selection of objectives, the level of cooperation with local guerrillas, etc. It would also be the major source of combat motivation for all soldiers involved in what they would come to see as a common cause.

Wingate knew that this particular concept would make him unpopular among many of his superiors yet he pursued it regardless, convinced that not only was he right, but that his opponents were wrong, in some cases egregiously so.

He took serious personal risks for ideals he believed in throughout his life. For instance, he allowed the Jewish underground militia, the Haganah, to infiltrate his Night Squads to be trained by the British Army and then used them to secure the areas around Jewish settlements in pursuit of Zionist policy — something which the British colonial office had proscribed. Furthermore, he openly advocated a partition plan drawn up by the Zionist leadership, to the point of lobbying the Colonial Secretary while he was still a serving captain in an army which expressly forbade its members from active involvement in politics.

Not surprisingly, Wingate’s Jewish volunteers came to admire him; he made their cause his and more, he was willing to risk everything for it.

It was to Wingate’s lasting disappointment that the Ethiopian resistance did not live up to his expectations. He arrived in the region as a passionate supporter of the cause of Haile Selassie but soon discovered that the emperor was unpopular among his subjects. Indeed, Ethiopia under the Italians spawned an array of competing insurgent groups and even more ‘accidental guerrillas’, opportunists and bandits whose interest in the war was confined largely to what they could steal. It is interesting to read his correspondence from this time, seeing his growing cynicism and, indeed, towards the end, his requests to his theatre commander to be reassigned.

Chindits lived off the land in the remote jungle mountains of Burma. (Image source: WikiCommons)

Chindits lived off the land in the remote jungle mountains of Burma. (Image source: WikiCommons)

Wingate on Taking Risks

Wingate practiced leadership-by-example. He commanded from the front tactically as well as strategically, and expected those around him to do likewise. He never made his men do anything he wouldn’t do himself, but he was invariably better at the job. He personally took charge of his men’s training, even as a brigadier, demonstrating the techniques he wanted them to absorb, including strenuous physical activities like combat swimming. Because of this, as one former Chindit put it to me: ‘We knew what he wanted from us, and that he knew what he was talking about, from the moment he arrived.’

A key feature of his times in Palestine and Ethiopia was his taking personal command of patrols deep into enemy territory and even the occasional night-time assault, frequently coming under enemy fire, getting within grenade range on at least one occasion, and being wounded seriously.

Wingate on Setting Goals

Wingate set the bar high, perhaps too high.

During the Chindit’s first operation some 600 men out of an 1,800-strong force did not come back. Some were killed in combat, others fell to disease or exhaustion. Wingate drove his men as hard as he drove himself. He could not understand why they couldn’t march 40 miles a day through rugged jungles in 45 degree heat and 100 per cent humidity like he could. Likewise, his habit of leading from the front whenever he could caused problems earlier in Ethiopia where he effectively disappeared into the battle for almost a week, leaving the wider campaign in disarray.

Orde Wingate with his Chindit commanders days before his death in March, 1944. (Image source: WikiCommons)

Orde Wingate with his junior officers prior to his death in March, 1944. (Image source: WikiCommons)

Wingate on Trusting Subordinates

Good leaders must be good delegators. But this requires professional and trustworthy officers as well as recognizing and developing talent in others and being secure enough not to see others as competitors.

In Ethiopia, Wingate was saddled with inexperienced junior officers, many of them essentially civilians in uniform who were assigned because they had local knowledge. While he certainly believed in his liberationist mission, a couple of his officers lost perspective and became partisans for various Ethiopian warlords, often to the detriment of the mission as a whole. Fortunately, he had more success with his officers elsewhere.

In Palestine, among his Night Squads trainees and junior commanders was Lieutenant H.E.N. Bredin, who also rose to the rank of major general in the British army, two other officers who became battalion commanders in the Second World War, and three future generals in the IDF, including Moshe Dayan and Yigal Allon.

Likewise, in Burma he was fortunate in having as his principal subordinates Michael Calvert, a seasoned unconventional warrior who would go on to re-form 22 SAS after the war, and Bernard Fergusson, an experienced regimental and staff officer with superb personal connections and one who was unafraid to disagree with him in public.

This suited Wingate, who gave his Chindit commanders considerable devolved authority and expected them to show initiative at all times.

In Summary


Orde Wingate’s experiences from World War Two offer lessons for 21st Century military planners, particularly in the areas of counter-insurgency, covert and special operations and proxy wars, all of which are likely to be with us for some time to come. And he has a lot to say about the role of leaders in this sort of operation too. Above all, they should be ‘true believers’ in the cause, or at least understand it, they should command from the front, and they should be left alone to exploit the situation as they see fit.

Dr. Simon Anglim is a teaching fellow in the Department of War Studies at King’s College London. His latest book is Orde Wingate: Unconventional Warrior, published by Pen & Sword Books. This article was adapted from a piece published on The Strategy Bridge.

2 comments for “Wingate’s Way – Leadership Lessons From Britain’s Maverick General Still Ring True Today

  1. Veritas
    14 January, 2016 at 1:09 am

    Superb article.

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