19. Resulting in the loss of the Mediterranean island to the Axis powers, the Battle of Crete saw paratroopers used for the first time en masse by Nazi Germany to impressive and ultimately devastating effect
Garrisoning in Crete following the Italian attack on Greece, the Mediterranean island provided the British Royal Navy with strategically valuable harbors used to great effect, most prominently during the evacuation of 57,000 Allied soldiers following the fall of Greece in April 1941. Although opposed by German High Command, who preferred an undivided focus on Operation Barbarossa, both the Luftwaffe as well as Hitler himself strongly supported an attack on Crete to regain prestige following the Battle of Britain and deny the island to the Allies. Starting on the morning of May 20, 1941, the Battle of Crete begun with an airborne invasion led by German paratroopers.
Suffering overwhelming casualties on the first day, with one German company from the 1st Assault Regiment enduring 112 deaths out of 126 men deployed, by the end of the first day the Allies were confident the onslaught could be held back. However, on the second day the Germans successfully cut communication, leading Allied commanders in the east to believe the west had already fallen. Consequently declining to send reinforcements, believing the situation was futile, this tactical failing allowed the Germans to land additional troops and engulf Allied defensive positions. Forced to evacuate, by the end of the battle on June 1 the Allies had suffered a total of 23,000 casualties to less than 6,000 by the Germans.