The Cantankerous, Eccentric Genius Whose Guerrilla Tactics Drove Italy Out of Ethiopia

It was the moment Ethiopian emperor Haile Selassie had dreamed of since Benito Mussolini’s army had taken over Addis Ababa and gained control of Ethiopia five years earlier. On May 5, 1941, the emperor jubilantly reentered the capital city in an open car captured from the Italians.

Leading the parade on a prancing white horse was Lt. Col. Orde Wingate, a small, fierce-faced man smartly turned out in a British Army uniform and sporting a pith helmet. Gleeful supporters poured down from the neighboring hills, while thousands of members of a local partisan group called the Patriots, as well as British, Kenyan, and South African soldiers, lined the streets, waving British and Ethiopian flags. Lt. Gen. Alan Cunningham, commander of the British forces in East Africa, welcomed Selassie in an official ceremony full of toasts and speeches. That night, the emperor slept in his own palace, the Little Ghebbi.

Haile Selassie’s triumphant return to Addis Ababa, carefully orchestrated by a Britain desperate for some good news in its lonely war against the Axis, symbolized the end of the Italian occupation of Ethiopia. Several weeks later, the Italians there would surrender to the British, a critical early Allied victory in World War II. And at the heart of that victory was the controversial, iconoclastic — and many would say brilliant — Wingate.

Wingate certainly had his faults and peculiarities. He had a penchant for conducting staff meetings while emerging naked from the bath, and often wore an onion on a cord around his neck, believing it to be medicinally imperative. Bouts of depression laid him low at the most inopportune times. His hypercritical views of the British Army rubbed many of his commanders and subordinates the wrong way, and even his admirers were struck by his visceral, often instantaneous unpopularity.

For all that, he was later referred to as a genius by no less than Winston Churchill for his daring exploits as the leader of the Chindits, the special guerrilla force in Burma that would play such a vital role in 1944 and 1945 in turning the tide in favor of the Allies in the Far East against a much larger Japanese army.

But it was in Ethiopia in early 1941, and to a lesser extent in Palestine in the 1930s, that Wingate developed the “long-range penetration” guerrilla tactics that would make his more famous exploits so successful. In Ethiopia he led a group of specially trained Anglo-Ethiopian guerrillas that he dubbed the Gideon Force, after the biblical hero who destroyed a much larger enemy with only a few hundred men. His men infiltrated Italian lines, provided critical intelligence to the British High Command, and sowed panic with swift, brutal night raids. Wingate capped off the campaign in May 1941 by persuading 12,000 Italian troops to surrender to his 2,000-man force. As his colleague Sir Wilfred Thesiger later mused, “Wingate deserved a knighthood for what he did in Ethiopia.”

Wingate’s unconventional youth

Orde Wingate’s upbringing shaped him into the cantankerous, intransigent character he became. Born in India in 1903, he was raised in England by a strict, fervently religious family with military roots (T. E. Lawrence, better known as Lawrence of Arabia, was a distant cousin). From a very young age, he was encouraged to be bold and self-reliant—which could and did foster rebelliousness.

At the Army Equestrian School at Weedon, Wingate annoyed his instructors by interrupting mealtimes with harangues on such polarizing subjects as Marxism, which he claimed to embrace. As one contemporary recalled, “He and I had one basic common belief: Regulations are made by sods for fools, and they are to be circumvented and not obeyed where inconvenient.”

By young adulthood, Wingate was suffering from undiagnosed clinical depression. Some have suggested that he exhibited classic symptoms of bipolar disorder. He would experience extreme highs and lows—flashes of confident exuberance, punctuated by what he described as “nervous attacks,” or his “particular curse.” Whatever the correct label, his mood fluctuations only underscored his growing reputation for peculiarity and unpredictability.

Early on, Wingate was greatly influenced by his father’s cousin, Sir Reginald Wingate, whom Orde called Cousin Rex. A retired army general who had served as governor-general of Sudan from 1899 to 1916 and high commissioner of Egypt from 1917 to 1919, Cousin Rex instilled in Wingate a keen interest in Middle Eastern politics and culture that over the years would curdle into obsession.

Wingate was accepted into the Sudan Defence Force in April 1925 and posted to the East Arab Corps. The SDF was considered quite glamorous — in many ways a precursor to the British Special Air Service and other special ops forces that were created during and after the war. Wingate served on the Ethiopian border, where the SDF prowled for slave traders and ivory poachers.

As Wingate moved away from regular patrolling to conducting baited ambushes, he honed the tactics that he would later use so well in Palestine, Ethiopia, and Burma.

His efforts did not go unnoticed. After one such mission, in which Wingate’s men killed one poacher and captured 13 more, Sudan’s governor general praised him for his “great dash and judgment.”

Nonetheless, Wingate made a mixed impression on his fellow officers. While they lauded his performance, they were put off by his scruffy appearance, his habitual nudity, and his tendency to make known his extreme political views. At one point, the colonel in command of the East Arab Corps warned him to keep his opinions to himself: “I don’t like the things that you say, and I don’t like you.”

Although compromise was not in Wingate’s nature, he knew he had to be at least outwardly mindful of such rebukes, for he had come to believe that the army was his path to greatness. “I cannot be a nobody,” he wrote home from Sudan. “I cannot be nothing!”

In 1933, Wingate returned to Great Britain, where he was assigned to retrain British artillery units. Three years later, he was posted to Palestine as an intelligence officer. It was unquestionably a turning point for him, as his ideas on special operations employing irregular forces began to coalesce.

‘Special Night Squads’ formed

In Palestine, he also found an outlet for his passion and energy. Wingate immediately identified with Jewish political leaders and, though he was not Jewish, became an ardent Zionist committed to the creation of a Jewish state in Palestine. Wingate later explained that his empathy stemmed in part from bullying he had suffered as a young boy. He admired the Jews for refusing, like him, to give up in the face of persecution.

Wingate proposed using small assault units of heavily armed Jewish commandos to combat Arab uprisings, and Lt. Gen. Archibald Wavell, then a commander of British forces in Palestine, approved the idea. In June 1938, the so-called Special Night Squads were created, with Wingate assigned to train them and lead their patrols. Most of their actions consisted of ambushing Arab saboteurs who were attacking British pipelines, but Wingate also led brutal reprisal raids on villages suspected of harboring the saboteurs.

For his work with the Special Night Squads—which helped to quell Arab uprisings and taught a future generation of Israeli generals how to fight—Wingate was awarded Britain’s Distinguished Service Order. But his increasing involvement with Zionism disturbed some of his superiors, one of whom labeled him a security risk. When a fellow officer pointed out that there were two sides to the Palestine problem, Wingate replied, “I know that. I just happen to be on the right side.”

Once again undermined by his passion and personality, Wingate was removed from command in 1939 and ordered back to Great Britain.

ethiopia becomes pivotal

After Italy declared war on France and Great Britain on June 10, 1940, the Allies concluded that the liberation of Ethiopia was essential to their success in Africa — or, at the very least, to protecting the pivotal British supply routes on the Suez Canal’s Red Sea flank. In late June, the British government promised to restore Haile Selassie to the throne and transported him from England, where he had been living since the Italians banished him in 1936, back to Africa, where they hoped his arrival would galvanize his countrymen to fight back against the Italians.

The British regular forces needed the help: They were stretched thin and vastly outnumbered by the Italians. General Wavell had 80,000 British and Commonwealth troops at his disposal to handle potential conflicts in Libya, Iraq, and East Africa; the Italians had some 250,000 soldiers in East Africa alone. At a meeting in October attended by the emperor, it was agreed that irregular forces would be a critical part of the plan to seize Ethiopia from Italy.

Meanwhile, Wingate was commanding an antiaircraft unit in England and itching to get back into action, preferably somewhere he could put his theories on guerrilla warfare to use. Fortunately for Wingate, he had an admirer in Wavell, who requested his assistance with the upcoming Ethiopian campaign.

In December 1940, Wavell convened a conference in Cairo on the upcoming East African offensive. Wingate elaborated there on the guerrilla tactic he proposed: long-range penetration, which he described as “regular warfare behind enemy lines.” He called for the creation of a small force of well-armed, highly disciplined men that could paralyze much larger forces. The troops would need to have a unified command and a clear objective— in this case, ejecting the Italians from Ethiopia and restoring Selassie to the throne.

Wavell approved the plan, and so was born the Gideon Force—composed of 2,000 veteran Sudanese and Ethiopian soldiers, several mortars, and 18,000 camels (to carry men and supplies), and led by some 70 British officers and NCOs. On New Year’s Eve, an ebullient Wingate dashed off a two-and-a-half-page letter to British headquarters reflecting on his vision and his hopes for what lay ahead: “Every weapon, every round, every vehicle, gall of petrol, pound of gelignite, that comes now is going to its destination under the enemy’s ribs.”

By the beginning of 1941, the British had orchestrated a plan of attack in Ethiopia. Lt. Gen. William Platt, who commanded the Sudan Defence Force, would move in from northern Sudan, and General Cunningham would advance from Kenya into southern Ethiopia. Wingate would press forward into the Gojjam Province in northwest Ethiopia, isolating and taking several fortresses and cutting the road between Addis Ababa and Debra Markos, the capital of Gojjam. The Gideon Force would also escort Haile Selassie back into his country in a series of staged moves. In Gojjam, Wingate would meet up with Col. Daniel Sandford, who was already leading a force of native partisans known as the Patriots in an operation called Mission 101.

By now Wingate’s fondness for Haile Selassie—whom Wingate had first met in Sudan in 1940, and whose temporary residence some 30 miles south of Khartoum, the Pink Palace, he visited regularly—had deepened into a zealous protectiveness. Wingate was inspired by the David-and-Goliath aspect of the emperor’s mission and by its motifs of resurrection and rebirth. Convinced that Haile Selassie had been unjustly robbed of his kingdom, Wingate preached to his officers the moral imperative of liberating small, oppressed nations like Ethiopia, and gave a similar message to the emperor.

“I told him,” Wingate later wrote, “that he should take as his motto an ancient proverb found in Gese, ‘If I am not for myself, who will be for me?’ and trust in the justice of his cause.”

Gideon force mobilizes

In the first weeks of 1941, the Gideon Force moved into the Gojjam Province. Leading the way was Wingate, occasionally wearing an alarm clock on his wrist as a lesson to his soldiers in punctuality. On January 20, Haile Selassie planted the royal flag on Ethiopian soil for the first time in five years. Wingate was at his side, having choreographed every aspect of the emperor’s historic return—down to insisting on a proper flagpole.

“The Emperor proposes to haul the flag up himself, so we don’t want anything to go wrong,” he warned his men.

In early February, Selassie and Wingate arrived in Belaya in the Gojjam Province, where the emperor established his headquarters. From there, the Gideon Force launched its Ethiopian campaign in earnest, intimidating the Italians with a shrewd blend of propaganda and force, of surprise and bluff. For starters, Wingate’s men rallied the Ethiopians by speaking through powerful loudspeakers and megaphones, as well as distributing tens of thousands of handbills (printed on the Gideon Force’s portable press) to announce the emperor’s return. The tactic not only encouraged Ethiopians to desert the Italian army but further rattled the already skittish Italians.

Wingate knew that they must move as quickly as possible toward Debra Markos, some 100 miles to the southeast. A delay might give the enemy a chance to decipher the Gideon Force’s weaknesses, namely, its inferior numbers. His goal was to besiege the Italian garrisons with nighttime attacks in the hope that the Italians — whom he despised as soldiers — would assume they were facing a far greater force than they actually were.

“The vivid imagination of the enemy was always ready to picture a company as a division for the first two days following its appearance,” he explained. “It was essential to maintain the element of surprise, if benefit were to be obtained from his credulity and cowardice.”

The Gideon Force thus pursued enemy encampments along the road to Debra Markos with one piercing night attack after another. Wingate’s men functioned much like the World War I trench raid teams: crawling up to the enemy camp, unleashing grenades and mortar shells, and then evaporating into the night.

Wingate himself leads raids

Wingate led as many raids as he could. Some in the British High Command criticized this practice as heedless showmanship. But Abraham Akavia, Wingate’s aide in Ethiopia, insisted Wingate’s leadership by example was sound, because it raised the “morale and the fighting abilities of such a small force, by providing men with his personal example and the officers with continual tactical training. In addition, as the record of these operations clearly proves, the chances of success were much higher when Wingate personally took part in the action.”

In fact, Wingate built up a strong camaraderie with those in his force. As Akavia wrote after one attack: “As usual, Wingate demanded fast movement, mobility being one of the main advantages of the Gideon Force, and he rushed from one place to the other, goading everybody to superhuman effort…and his shouts seemed to have an immediate effect on the soldiers who admired so much this strange Britisher, who had led them so successfully to battle and had shared in all of their perils and discomforts throughout the fighting.”

After a brief battle at a fort near Debra Markos, the Italians finally deserted the city on April 3, 1941. At the same time, Italian forces under Prince Amedeo, the Duke of Aosta, pulled out of Addis Ababa and headed north toward the mountains of Amba Alagi. On April 5, after the South African Air Force had bombed Addis Ababa, British regular troops under General Cunningham occupied the city. The next day, Haile Selassie entered Debra Markos.

By May 1941 the Italian efforts were falling apart all over Ethiopia. But other strategic issues were weighing on the British: Greece had fallen to the Axis, and Gen. Erwin Rommel was advancing into the western desert. A speedy resolution to the Ethiopian campaign was imperative.

The Gideon Force concentrated on ensuring Haile Selassie’s safe and celebratory march from Debra Markos to Addis Ababa early that May, on the fifth anniversary of the city’s capture by the Italians. Wingate wrote part of the conclusion of the speech that Haile Selassie gave to his followers in the capital— a testimony to how close the two men had become:

“St. George who slew the dragon,” he wrote, “is the patron both of us and of our allies. We should therefore fasten our friendship forever in an indissoluble bond, to defeat this ungodly and newly appointed dragon that vexes mankind. Our allies are our friends and our own blood. Take them to your hearts!”

Selassie warmly returned the sentiment: After the East African campaign, the emperor sent Wingate four gold rings in appreciation of all that he had done.

Bluffing the italians

With the emperor firmly installed, the Gideon Force left Addis Ababa to join Mission 101, which was harassing Col. Severio Maraventano’s withdrawing troops. But the Patriots faced a debilitating shortage of food and arms, and just as he reached them, Wingate received orders to stop chasing Maraventano and help British forces elsewhere.

Instead, he pretended that he could not decipher the message and continued to fight.

Maraventano, too, was running out of food, arms, and medical supplies, setting the stage for Wingate’s final triumph in Ethiopia. Nearly out of ammunition himself, though, he could not rely on the Gideon Force to take the Italians by arms.

It was time to bluff.

Wingate sent Maraventano a letter indicating that he was about to be joined by many additional troops, as well as large-scale air reinforcements. He also stressed that unless Maraventano surrendered, his troops would be left to the mercy of the Patriots, thus playing on the Italians’ deep-seated fear of the partisans: brutal captors who were said to castrate their prisoners.

Maraventano pondered the message, but not for long. On May 23, 1941, he surrendered his 12,000-man force to Wingate. It was a spectacular bluff: not only were no reinforcements of any kind expected, but Wingate’s force of 2,000 men was dwarfed by the size of the Italian army. Within days, the Duke of Aosta and Gen. Guglielmo Nasi surrendered also, and the Italian reign in Ethiopia was over.

It should have been a victory to relish. Wingate’s long-range penetration tactics had proven extremely effective, the emperor had been reinstalled, and he had beaten vast and potentially overwhelming forces. But his temperament again tarnished his success. Wingate’s behavior, unpredictable and often uncalled for, had instigated clashes with several British colleagues throughout the campaign, and once, infuriated by a minor transgression, Wingate shocked onlookers by smacking his Ethiopian translator in the face.

wingate pens appalling report

Ultimately, Wingate’s renegade exploits in Ethiopia only reinforced the view held by many of his superiors that he was arrogant and defiant, and should be kept on a very short leash. As soon as Wingate and the Gideon Force delivered their Italian POWs to Addis Ababa, he was summoned to headquarters in Harar, where he was informed that the Gideon Force was being disbanded immediately, and was ordered to leave for headquarters in Cairo. It was an ignominious end, and Wingate was particularly incensed that he was forced to leave East Africa without saying goodbye to Haile Selassie.

In Cairo, Wingate was for the most part ignored, if not outright ostracized. And he did himself no favors by writing a self-serving, vitriolic report on the Ethiopian campaign. In highlighting his stringent views on the use of long-range penetration, he also indicted the entire British campaign. He portrayed the British NCOs who served under him as “the scum of the army,” described some of his commissioned officers as “mediocre and inferior,” and called his signalers “lazy, ill-trained and sometimes cowardly.” And he labeled generals Cunningham and Platt “military apes” for having the gall to shut down his Gideon Force.

Even Wingate’s staunchest supporters were appalled. The document “would almost have justified my placing him under arrest for insubordination,” Wavell later said.

By the summer of 1941, all Wingate’s thoughts and hopes were falling on angry, deaf ears. In early July, ill with the malaria he had contracted in Ethiopia and deeply depressed, he stabbed himself in his hotel room, but was discovered before he bled to death. Word of Wingate’s suicide attempt reverberated throughout Cairo, fueling the empathy of those supporters who felt that he had been shabbily treated — and the unmitigated contempt of his enemies. One of his superiors visited him in the hospital, only to hiss, “You bloody fool. Why didn’t you use a revolver?”

Wingate traveled back to England in September 1941. Unbowed, his first words to his doctor were, “You know, I am not the only great soldier who has tried to commit suicide. There was Napoleon, for instance.”

wingate reapplies tactics with chindits

At the urging of several backers — Cousin Rex included — who were in a position to help Wingate resurrect his reputation as an innovative leader and tactician, he toned down his report on the Ethiopian campaign and resubmitted it. The new version, which jettisoned much of the inflammatory language of the first and stressed his recommendations for future guerrilla operations, was then circulated at the highest levels, eventually reaching Winston Churchill.

Impressed with its insights, Churchill referred it to Wavell, by then commander in chief of the Far Eastern theater.

It was the reprieve of a lifetime for Wingate — and a stroke of good fortune for the Allied forces there. In early 1942, Wavell called Wingate to Burma and asked him to command irregular forces that would operate behind Japanese lines, much like the Gideon Force had done in Ethiopia. Wingate quickly formed what some historians consider the most controversial British unit of the war, the Chindits.

Over the next three years the Chindits would refine the concept of long-range penetration Wingate had conjured in Palestine and Ethiopia, sending hardcore special forces (including Americans) deep into the jungle, often behind enemy lines, to cut Japanese lines of communication, collect intelligence, and otherwise wreak havoc.

Despite their successes in Burma, however, the Chindits suffered heavy casualties, leading many to question the unit’s overall strategy and relative merit. But Wingate would never have to defend his brainchild. In March 1944, the Chindits were several weeks into a major operation—and at the height of their popularity with the British High Command—when Wingate was killed in a plane crash as he was flying from Burma to a conference in India.

It seems that it was only in death, and even then a bit obliquely, that Wingate finally received the admiration and appreciation he had so intensely desired. “There was a man of genius,” Churchill told the House of Commons after Wingate’s death, “who might well have become also a man of destiny.”

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Originally published in the April 2010 issue of World War II magazine.