Chaim Herzog, Israel's first Prime Minister, described him as "my favorite madman." As a British Intelligence Officer in Palestine in the late 1930's, he organized and led the Haganah Night Squads on deep strike missions against the fedayeen, adopting and adapting the Arab raiders' own tactics to use against them.
In Ethiopia (Abyssinia, at the time), Wingate formed the Gideon Force and led Ethiopian troops to their victory over the Italians in the early '40s. He put Haile Selassie (Ras Tafari, to you Bob Marley fans) back on the thrown. Having routed the Italians, he was ordered to stop short of entering Addis Abbaba with his indig forces; apparently British High Command was worried that his dusky warriors would celebrate their victory by raping all the white women in the ville. Wingate knew the symbolic importance of Salassie's taking the city and getting back on the thrown himself, so he asked his counterpart for his word that he wouldn't molest the ladies, it was granted, and Haile Selassie victoriously re-took Addis Abbaba.
Not long after his Italian campaign, Wingate had a total nervous breakdown and was institutionalized. He made a nominal recovery, and began trying to market an irregular warfare strategy for blocking the Japanese from reaching India with an unconventional combined force. Winston Churchill liked Wingate and his ideas and took him to meet Roosevelt on one of their secret rendezvous. Roosevelt saw the value of Wingate's plans and the two titular heads of the Western Allies turned him loose on Burma. Wingate organized and trained the Chindit force, and died in Burma.
"Wingate saw himself as a boot up the backside of Man. The fact that most of his ideas ran directly against those of his superiors did not worry him in the slightest."
Wingate's critics found him objectionable not only because of his commando-centric opinions of the waging of war, but also because of his personal eccentricities. During the after action debriefs of his Night Raid detachment in Palestine, he could often be found sitting on a camp stool in the corner of the command tent, naked, reading a Bible and munching on a raw onion. Officers that interviewed with him to serve with the Chindits in Burma entered his tent to find him naked on a cot, grooming his body hair with a tooth brush. They also documented that for physical training, he made the entire unit practice yoga (the guy was obviously a deviant).
It was in Burma that Wingate perfected the tactic of having his light, mostly indigenous forces execute deep penetrations behind Japanese lines, and then used his Allied air power to drop in the heavy weapons he needed to defeat the Japanese. This tactic was copied with great success by the OSS' Detachment 101.
Wingate is the archetype for letting a possible goofball run rampant in a military organization. Studying his campaigns and the maturation of his concepts of unconventional warfare is about as much fun as a student of military history is going to get. I apologize if this post isn't as detailed as one dedicated to Wingate should be; I don't have my stash of Wingate references to hand. Most of what's written here is pulled from memory from a Wingate article in No End Save Victory (which by the way, is an eclectic compilaiton of essays from notable historians on their favorite aspects of and vignettes from WWII with a slight tilt towards favoring Special Operations; this is one of those books that makes you smarter)
Many thanks to Bubby, who took a time out from his arduous PhD studies to find me the link above to a decent Wingate site on the web.