When You’re Outnumbered: Lessons from Two British Masters of Irregular Warfare


A British nudist who liked to give press briefings wearing only a pith helmet and boots and a dapper Scotsman partial to wearing kilts with his dress uniform in contravention of Army regulations have much to teach modern military strategists. During World War II these two British officers, Orde Wingate and Colin Gubbins, developed inventive applications of irregular warfare in high-intensity conflict against peer competitors. Their innovations provide constructive lessons for the U.S. military, particularly for the United States Marine Corps as it considers its new primary role as a counter-force in the Pacific as outlined in the recent Commandant’s Planning Guidance.

The interwar British Army found itself continuing to shoulder globe-spanning responsibilities, at the same time that much of the leadership could see the need to prepare to fight major power adversaries. After the Vietnam War the U.S. military largely chose to discard knowledge hard-won from jungle fighting to focus on Soviet hordes in the Fulda Gap. Similarly, after two decades of counter-terrorism, many reject the idea that there is anything to learn from these low-intensity conflicts (the wars in Afghanistan, Iraq, and other theaters of the “Global War on Terror”) and want to shift focus instead to conventional great power threats.



Nevertheless, lessons from Wingate and Gubbins’ irregular warfare experiences offer two models of continued relevance for future high-intensity warfare. First, relying on American special operations forces is not enough. Instead U.S. conventional forces should staff and train trusted partners and create hybrid units with foreign partners. U.S. officers and non-commissioned officers can provide the backbone for tactical command and staff work and can direct indigenous forces. In wartime these units could conduct operations against the adversary in enemy (or contested) territory using guerrilla-style attacks and sabotage in support of conventional operations. Working with, training, and preparing foreign forces now to conduct stay-behind operations would be a force multiplier in future conflict. Countries agreeing to such a partnership may also see a benefit from powerfully allying with the United States. Second, the U.S. military should establish specially provisioned, conventional forces in approximately company-sized units designed to conduct long-range penetration operations against enemy lines of communication. They should be able to operate for up to a month or longer without resupply.

Wingate and Gubbins, both artillery officers and graduates of Woolwich Military Academy, were influenced by their Scottish heritage and their experiences in various theaters on the edges of the British Empire. They had different personalities and leadership styles, but both came to see that unconventional warfare — including the use of auxiliary or foreign forces — could be a force multiplier in conventional warfare against peer adversaries. Wingate is most well-known for his activities in Palestine, Abyssinia, and later Burma with the famous Chindits. (The name was a corruption of the Burmese chinthe, a mythological lion-like creature that frequently guards Buddhist temples in pairs of statutes.) Gubbins’ great contributions were his development of doctrine and training for the Special Operations Executive, and later his operational contributions when he later became the head of the organization. The British Special Operations Executive directed subversion and sabotage against Axis forces in occupied countries and directly influenced the organization and training of the U.S. Office of Strategic Services, the progenitor of the CIA and U.S. Army Special Forces. (Unlike the U.S. Office of Strategic Services, the British Special Operations Executive did not have an intelligence component, and instead focused purely on subversion and sabotage).

Orde Wingate

The geographic span of Wingate’s influence is considerable. There’s an Israeli sports and military training institute named after him, in addition to dozens of streets, and an eponymous school in Ethiopia. His remains are interred in Arlington National Cemetery alongside those of the U.S. bomber crew with whom he died in India. He regularly alienated his superiors as well as his peers, but developed influential patrons including Winston Churchill. Churchill eulogized Wingate as “one of the most brilliant and courageous figures of the second world war.” The British prime minister claimed that he “recognized him as a man of genius, and I hoped he might become a man of destiny.” Israeli Prime Minister Yitzak Rabin credited Wingate as having possibly the “largest influence on Israeli military theory and practice.

Wingate was raised in an austere Protestant household, became an ardent Zionist (and was close to Chaim Weizmann, Israel’s first president), dabbled in Marxism, and broke a years-long engagement to marry a teenager more than a decade his junior. He was an eccentric who in the field often ate raw onions while naked but for foot and head-gear, and scrubbed himself with a rough brush rather than bathing, and did not believe in brushing his teeth. Wingate was also manic-depressive, and while wrestling with a bout of cerebral malaria stabbed himself twice in the neck in a suicide attempt in Cairo.

Like several other military geniuses and iconoclasts (such as Lt. Col. Earl “Pete” Ellis, Brig. Gen. William “Billy” Mitchell, and Col. John Boyd), Wingate had “‘amazing success’ in getting himself disliked by people who might otherwise have supported him,” according to Adm. Louis Mountbatten, the Supreme Allied Commander, South East Asia Command. Nevertheless, Wingate typically engendered great loyalty not only in his British subordinates, but also the foreign fighters he fought with in Sudan, Palestine, Ethiopia, and Burma.

Colin Gubbins

Gubbins was in many ways Wingate’s polar opposite. He was described as genial, calm, charming, and soft-spoken, as well as energetic and efficient. At a time when his society was notoriously fixated on class, he was a rare general officer who mixed freely among all ranks, and was seen as ahead of his time in how he treated female staff. One of his principal secretaries remembered that he would not tolerate any discrimination in how women working for the Special Operations Executive were treated.

Gubbins was an experienced officer who fought for four years on the western front of World War I until he was wounded. Following the war he had a diverse series of assignments including service in the Archangel campaign aiding the White Russian forces; countering the Irish insurgency as British troops withdrew during the Anglo-Irish war; frontier duty in India; and leading an independent company tasked with slowing down the Nazi invasion in Norway. In designing doctrine for Special Operations Executive Gubbins studied history closely — drawing lessons from British adversaries, including the Irish, the Boers, and the German Col. Paul Emil von Lettow-Vorbeck’s successful World War I campaign against the allies in East Africa. He took on the Special Operations Executive mission despite knowing that the British bias against unconventional warfare service would likely negatively impact his promotion potential. (Wingate was conscious of this bias as well, which is why he was loath to fall under the Special Operations Executive, and fought to keep his forces conventional.) Gubbins’ son joined the Special Operations Executive and was killed at Anzio. Unlike Wingate he was gracious and took slights without complaint, notably after the war when his rank was reduced from brevet major general to his pre-war rank of colonel, impacting his pension and requiring him to seek additional work in his retirement.

Use of Local Forces

What relevance do Wingate and Gubbins have today? Both were products of an expeditionary army that had frequent practice in “small wars,” often leading native troops, and were used to fighting at a far remove from their supply lines or reinforcements. In the British Army lessons were shared by officers who had served in varied environments and applied in other areas of the empire. Wingate and Gubbins’ biographies well reflect the typical diversity of assignments officers could expect at the time. Drawing upon their experiences, both focused on the use of local forces supported by British advisers to support larger conventional missions in World War II.

Special Night Squads

Wingate developed and led the Special Night Squads in Mandatory Palestine during the Arab Revolt of 1936 to 1939. Each squad was made up of a handful of British officers and non-commissioned officers, and staffed by Haganah (Jewish defense force) fighters. The Arab Revolt was directed not only against the British government, but also against the growing Jewish communities spreading throughout Arab territory. Wingate arrived in Palestine having studied Arabic and led Arab troops in the Sudanese Defense Force, but he did not suffer from the latent antisemitism that much of the British officer class often exhibited. Wingate saw that British tactics were failing, with truck-borne troops spotted long before they got to the scene of an Arab attack. With headquarters approval, he recruited from the illegal Haganah to develop his Special Night Squads. Wingate focused on speed, physical fitness, training, and the ability to operate at night. His squads took the offensive, and focused on developing intelligence, to lead to raids to generate additional intelligence, in a virtuous cycle. (Seventy-plus years later, U.S. Joint Special Operations Command perfected a similar intelligence – raid – intelligence cycle in Iraq.) While technically a counter-insurgency force, the squads operated much like guerrillas.

The Gideon Force

Wingate’s next venture was leading the “Gideon Force” in Abyssinia (December 1940 to June 1941), where his indigenous unit made up of Ethiopian troops coordinated and supported a larger conventional British campaign against Italian forces. Wingate led the forces that triumphantly reinstalled Emperor Hailie Selassie to his throne. (Interestingly, at the time, Wingate fell under MI(R) – the War Office’s “Research” branch in Ethiopia, which later along with Section D from the British Secret Intelligence Service was combined into Special Operations Executive). The Gideons operated similarly to the Special Night Squads, crossing terrain assessed as impassible, using physically hardened troops, camels, and other pack animals to surprise the Italians. They employed hit-and-run tactics successfully in situations as lopsided as 300 versus a force of 12,000 Italian and colonial troops. With a focus on mobility and rapid action at decisive points, Wingate’s forces applied maneuver warfare. At one point, 1,000 Ethiopian and Sudanese troops in the Gideon Force with 500 in reserve drove 7,000 Italians into a rout. One final battle resulted in 7,000 colonial troops (of which 1,100 were Italian members of “black-shirt” battalions) surrendering to 35 Sudanese fighters. Ultimately, the Gideon Force was credited with defeating an Italian army more than ten times its own size as it liberated Abyssinia. While Wingate advocated for the development of British special forces (contemporaneously, others were establishing the Commandos and Special Air Service), his units of local volunteers were led by regular British troops — in many cases “territorials,” which approximate today’s U.S. National Guard or reservists. He also saw that his unconventional warfare forces were designed to operate in support of a larger conventional mission.

Special Operations Executive

Gubbins arrived in Poland just days before the Nazi and Soviet invasions as a liaison officer to prepare to conduct guerilla warfare, but quickly had to retreat. A similar attempt to coordinate with the Czechoslovakian and Polish general staffs in Paris failed. He helped plan internal British resistance to a Nazi invasion, and then served in Norway. After these initial back-foot efforts, Gubbins came to MI(R), the War Office’s “research” branch — which developed into the Special Operations Executive and was placed in charge of doctrine and training. Gubbins devised a strategy to work with governments in exile to identify and train locals for sabotage operations in their home countries. A central element of Special Operations Executive was its focus on coordinating attacks to support overarching strategic goals. Ultimately, Special Operations Executive pursued a two-phased approach. To begin with, small units of well-trained elite saboteurs carried out specific missions to damage enemy infrastructure (such as critical plants for war materiel). In the second phase Gubbins envisioned moving to larger formations of less-trained resistance forces (much like Mao Zedong’s theory of insurgency), who would attack enemy lines of communication in support of the allied theater commander’s offensive operations as nations were liberated.

During phase one, native units also created covert smuggling “rat-lines” into occupied territories. One such Special Operations Executive maritime unit was the “Shetland Bus” — a fleet of Norwegian fishing vessels used to infiltrate and exfiltrate men and equipment in occupied Scandinavia. Gubbins’ doctrine focused on surprise, maneuver, and peripheral attack. Plans for breaking contact and escape were essential. He recommended pinprick night attacks to sap the morale of the enemy. Successful guerrilla attacks cause an enemy to disperse forces to protect their rear areas and supply-lines.

U.S. Special Operations Command units do train partner forces, and thus it may be argued that the British example has already been adopted. In addition to the standard foreign internal defense missions, so-called “127 Echo missions” allow units to develop foreign counter-terrorism forces in this manner. Per 10 U.S. Code Section 127e, the Pentagon can spend up to $100 million annually on support to foreign forces for counter-terrorism operations. In these programs foreign units conduct combat operations with US operational guidance. However, unlike 127e programs the Special Night Squads and the Gideon Force in Ethiopia were directly led by conventional British officers and non-commissioned officers embedded in those units.

The famous Special Operations Executive Jedburgh teams of 1944-45 (in which a British or American officer, a radio operator, and a local translator parachuted into occupied territory to coordinate with local partisans — primarily in the European theater, but also in the last months of the war in Asia) — similarly provided a trained component embedded in an indigenous force. Like the British imperial army, the Marine Corps history has been that of an expeditionary force, frequently used as an “imperial constabulary” and fighting “small wars.” Conventional Marine units have often found themselves partnering with local forces. Many argue that their embedding with indigenous partners in initiatives such as the “Combined Action Program” in Vietnam were successful force multipliers for American efforts in that conflict.

Establishing partner forces in the Pacific now may allow greater operational flexibility for American forces in a future Asian war. At a minimum U.S. Marines should train foreign units that would allow Marines to fall into leadership billets during a conflict, and/or preparing them to conduct sabotage missions. Similarly, partner forces in the Baltics could address European security needs. A Pacific conflict is expected to be quick and brutal, and the United States will not have an opportunity to move forces into theater to extensively train partner forces. Marines will have limited resupply, and be required to operate for extended periods on their own. Thus, developing trained units now who have local knowledge may be crucial for future success.

Long-Range Unconventional Forces

Wingate may be most famous for his Chindits program, which should be considered as two separate campaigns in which British forces conducted long-range penetrations of Burma, directed against Japanese lines of communication. The first was more of a proof of concept to show that, properly equipped and trained, a brigade-sized British force dispersed into smaller columns could operate in the jungle against the enemy more than 100 miles from friendly forces. In February 1943, Wingate led his first foray against the Japanese. This first campaign showed that the Chindits were able to carry out ambushes, destroy bridges, and harass the enemy. They used air-drops for resupply, and without organic artillery assets instead called for air strikes. They lost nearly a third of the men who started the campaign and of those who returned roughly a quarter who survived were still combat effective, but the first Chindit force had a psychological effect — damaging Japanese morale, and lifting British spirits as a first successful offense in the Far East.

Wingate sought to sell his concept of long-range operations to British leadership and succeeded in reaching Churchill’s attention. The prime minister brought Wingate with him to the August 1943 First Quebec Conference between the United States, the United Kingdom, and Canada to brief the participants about the first successful Chindit mission. Having gained the prime minister’s support, Wingate returned to the British Army headquarters in India, and was given the equivalent of an Army Corps for his second Chindit mission. Training and organizing commenced in late 1943. Wingate again divided his units into “columns” roughly approximating a reinforced rifle company of 250 soldiers along with a command element, a recon platoon, heavy machine-gun platoon, mortar section, and indigenous troops from the Burma Rifles. In February 1944, Lt. Gen. William “Bill” Slim, commander of the British Fourteenth Army, gave Wingate the order to carry out attacks against the Japanese rear and their lines of communication, and to cause as much havoc as possible to support the larger British offensive. This Chindit mission was aerially inserted with gliders, landing 9,000 men and 1,000 mules, to create strong points in occupied territory. The second Chindit campaign may be seen as a historical antecedent to two examples from the war in Afghanistan: the Operation Rhino raids by U.S. Army Rangers in October 2001 in Kandahar, and the use of Camp Rhino by Marine Task Force 58, which conducted an “amphibious” assault from the Persian Gulf. Wingate’s death in a plane crash ended his plan to use the Chindits as a long-range force and they instead became regular infantry for the remainder of the campaign.

Gubbins employed a concept similar to the Chindits when tasked with operating against the Nazis in Norway. Gubbins led an “independent company,” designed to engage in mobile harassment of the enemy with sufficient logistics to self-sustain for one month. The unit had its own engineers, signals, mortars, and anti-tank capabilities. They successfully slowed the German invasion and exfiltrated from Scandinavia with minimal casualties.

Certainly, U.S. forces have the capability for deep insertion into hostile territory and have done so in modern conflicts (e.g., the 101st Airborne’s 2003 air assault into northern Iraq during Operation Iraqi Freedom). The issues facing the United States in a potential war in the Pacific are not only those of “the tyranny of distance,” but also that adversaries have learned not to allow the United States to build up its logistics or operate from large land bases or carrier strike groups, and have greatly invested in anti-access/area denial weapon systems to keep U.S. forces from being able to operate effectively. The U.S. Marine Corps Expeditionary Advanced Base Operations is already an initial recognition of the need to distribute the force in the Pacific in smaller units to reduce their footprints.

For these reasons, there is value in examining Wingate and Gubbins’ use of small units that can operate independently with self-sustain logistics (or minimal outside logistic support) against numerical odds — inside the adversary’s anti-access/area denial curtain, on the enemy’s terrain or land he has captured — for extended periods of time, often with the coordinated assistance of local forces.


Both Wingate and Gubbins faced many of the same problems that modern planners face in designing units that can operate against a numerically superior enemy. Two insights appear to have particular salience still today. First, the use of irregular forces largely made up of foreigners with a backbone of British officers and non-commissioned officers was a force multiplier that had dramatic impacts in multiple theaters for the British. Local troops intuitively knew their environment, and were willing to defend their home country. The addition of the professional British staff-work and resources immeasurably improved their capabilities. Wingate’s Special Night Squads in Jerusalem and the Gideon Force that liberated Abyssinia, or Gubbins’ sabotage operations in occupied Europe and later resistance campaigns supported by the Jedburgh teams, all repeatedly demonstrated the utility of this approach. Second, the development of self-supporting maneuver units designed for long-range penetration operations in support of a conventional mission — as demonstrated by the Chindits and Gubbins’ independent company in Norway — helped contribute to the United Kingdom’s strategic goals and to the Allied victory against the Axis powers. Lessons from these two Pax Britannia practitioners remain salient for today’s centurions guarding Pax Americana.



Christopher D. Booth is a career national security professional, and formerly served on active duty as a commissioned U.S. Army armor and cavalry officer. He has extensive experience abroad, including assignments in war zones and austere environments in the Middle East, Central Asia, South Asia, and Europe. He is a distinguished graduate of Command & Staff College – Marine Corps University, where he was a fellow in the General Robert H. Barrow Fellowship for Strategic Competition from the Marine Corps University and the Brute Krulak Center for Innovation & Creativity, and a scholar in the Gray Scholars Program – Advanced Studies on Social & Political Conflict. He graduated from Vanderbilt University Law School, and received a BA from the College of William & Mary.

Image: IDF Archive