Orde Wingate: The Most Controversial British Commander of WWII

Orde Wingate enters Addis Ababa on horseback.

Orde Wingate was the most unusual British commander of World War Two. Loved by some of his colleagues and hated by others, his reputation remains controversial to this day.

An Unconventional Youth

Born to British parents in India in 1903, Orde Wingate grew up in Britain, living with other relatives at times when his parents were in India. His family was strict Plymouth Brethren – conservative, evangelical, non-conformist Christians. They worked hard to instill their values in Orde.

At school, he was friendless. Not playing games or attending assemblies singled him out as different. He had known few children when he was young and struggled to socialize. Coupled with a willingness to challenge authority, this left him isolated and lonely.

Orde Wingate in Palestine

Into the Army

In 1920, Wingate entered the Royal Military Academy at Woolwich. There he had similar problems to those he had at school. Harsh treatment by his fellow cadets left him determined never to be left at the mercy of mob rule.

In 1923, Wingate entered the Royal Artillery.

An encounter with a family member who had been Governor-General of Sudan encouraged him to look east, learning Arabic. In 1930, he became an officer in the Sudan Defence Force. There he gained experience of independent command, impressing his superiors but aggravating his peers, who found him personally unbearable.

The British Army was dominated by discipline and by the most conservative elements of the British upper class. It was not a place for dissent.


In 1936, Wingate was sent to Palestine as an Intelligence Officer.

The region was a mess. Its post-war carve-up by European powers had ignored local interests and broken promises. Jewish settlement created a backlash by Palestinians.

Wingate’s Old Testament upbringing and contacts in the Jewish elite led him toward Zionism. It further aggravated his fellow officers, who were mostly sympathetic to the Arabs.

Daniel Sandford, H.I.M. Haile Selassie and Wingate in Dambacha Fort

Worst of all, in army eyes, Wingate worked around the chain of command. By going straight to General Wavell, he got support for his rejected ideas. He set up, trained, and led Jewish militia units fighting against Arab terrorists.

In all of this, Wingate showed courage, intelligence, innovation, strong moral character, and an utter insensitivity to those who disagreed with him. These were the characteristics that would polarize opinions.


Wingate was back in Britain when WWII was declared. In 1940, he was sent to join forces fighting the Italians in Abyssinia. There, he impressed the local leader Haile Selassie with his enthusiasm for the fight.

Given command of Gideon Force, Wingate won significant victories against the Italians. He also learned a great deal about guerrilla warfare, including the value of effective radio communications and air supply.