Who was the most cowardly military leader in history?

There are several I could suggest. In the Jungles of Burma, Guadalcanal and Papua New Guinea the Japanese would get a soldier who could speak English to taunt the British, Australian and Americans throughout the night with things like.
“Tommy, we come kill you in the morning.”
“GI why you fight Japan, you die here soon?”
And such, the effect of this throughout the night had a serious effect on men’s morale, especially on raw troops, as it was meant to. The taunting had a secondary purpose, it sometimes caused Allied soldiers to shout a response. However hardened Japanese soldiers would then be able to pin-point their positions and infiltrate between them or sneak up and kill the soldier.
There is a story from the Burma Campaign in the fighting around Kohima in 1944 that a certain Japanese soldier was doing this, calling out to the British soldiers, when a Gurkha crawled over to the British commanding officer and said “Japanman, he make too much noise, many men not like,” and then disappeared into the darkness. A short while later there came a scream and then silence then the Gurkha returned, carrying a bag containing a Japanese head.
(A Japanese infantry from the Burma Campaign in 1942 uniform. Sometimes the Japanese would employ English speaking soldiers to shout taunts at the Allies from the depths of the jungle, this had a two fold purpose: to lower the morale of the enemy and to learn the whereabouts of those soldiers by getting them to shout back. His rifle is a Type 99 Arisaka.)
In North Africa and Italy the Free French colonial troops from the mountains of Algeria and Morocco called Goumiers had a fearsome reputation, they had a very nasty trick designed to lower the morale of the enemy. They would sneak up to an enemy position in the dead of night, kill only one soldier, decapitate him and then leave. The next morning the Germans would wake to find the headless body of their comrade. The message was clear, ‘we can kill you any time we want, it may well be your turn tonight.’
(Free French colonial trooper, a Moroccan Guomier. Recruited from the Atlas Mountains of Morocco and from Algeria they were widely feared by the Germans and Italian troops. They fought well in the mountains of Tunisia and Italy. Goumiers were also employed in the Allied invasion of southern France.)
Leaving WW2 we look at a tactic employed by the native Americans, especially the Comanche and the Apache in the old American west. To lower the morale of the enemy the Indians would take a captive and torture him throughout the night, the effect on the soldiers of hearing the screams of one of their comrades and being able to do nothing to help him can only be imagined. This tactic was not only employed by the Native Americans but also by the tribes of the Northwest Frontier (Pakistan and Afghanistan border) and by the Vietnamese and probably by the Japanese and others.
(Apaches would torture a captive for hours, hoping his screams would keep the soldiers awake and demoralize them.The rifle is a Trapdoor Springfield carbine.)
Another tactic that can only be used against an enemy that is vastly outnumbered is to simply display your army in full view of the foe, let them see your numbers and see how outnumbered they are. This is often done with a display of banners and military music from pipers and drummers. Let the enemy know that if they surrendered their lives would be spared but if they fought then not only the defending soldiers would be killed but if it was a city that was being attacked then every man, woman and child within the city would also be killed. Make an example of one city that had chosen to fight and then the next might well think twice about resisting, this was a tactic favoured by Genghis Khan and his Mongols.
(His Mongol Warrior, his weapon his the feared Composite Bow. The Mongols use terror as a weapon, wanting to avoid a siege if that was possible knowing that sieges were not only time consuming but also costly, they would make examples of cities that decided to resist by killing all the inhabitants and sparing those of cities that opened the gates to the Mongols. It was not unknown for the people to raise up and kill their own leaders if they had shown any inclination to fight)
Another people who preferred this tactic were the pirates from the Golden Age of piracy. Never knowing where or when they could get more men, pirates were understandably reluctant to get into a fight. It was much better if the pirates victim just gave up and allowed themselves to be plundered. Most pirates (there were exceptions of course) would spare the crew of a ship that did not resist. In fact it is known that 95% of Edward Teach’s (Backbeard) prizes were taken without a fight. Again it was not unknown for a ship’s crew to murder their captain if that captain was not determined to fight.
(Edward Teach, AKA Blackbeard. 95% of his prizes were taken without a fight. (As they were with most pirates.) His victims simply anchored and let him and his pirates board. His fearsome appearance and his habit of sticking lighted matches in his hair was also designed to cow any crew into compliance.)
Another tool is propaganda that can be broadcast to the enemy population by radio or by loudspeakers or by the dropping of leaflets. If properly done it can be effective but if it is crude (as it often is) is just provides the enemy with entertainment and something to laugh at.
It is known that during the fighting for Kohima one of the Royal Nepalese Brigades (these were not Gurkhas but regular soldiers from the Nepalese army sent to fight in Burma by the king of Nepal) deserted en masse after being bombarded with propaganda from Japanese loud-speakers. The Gurkhas must have been livid with shame by this display from their own countrymen, but Nepal’s army was poorly trained and motivated and in no way fit for the modern battlefield, some British staff officers had predicted their total collapse before they were deployed.
Propaganda can not only be used to lower the morale of the enemy but it can also be used to save lives and limit the shedding of blood. On Saipan and Okinawa thousands of Japanese civilians took their own lives rather than be taken captive by the Americans, yet thousands more were saved by careful propaganda from Japanese speaking Americans who persuaded them to surrender through loud-speakers, explaining that they would not be harmed and that they would be given food and medical attention.
(Americans use loud-Speakers on Saipan, trying to talk Japanese snipers and civilians hiding in caves on the seashore into surrendering. It had some success {Below} but many civilians and soldiers still took their own lives.)

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