Stalingrad is often described as the turning point of the German war with the Soviet Union, or perhaps even the entire European war. This paper argues that the actual turning point was probably earlier in the Barbarossa campaign, and that the decision to hold Stalingrad, while a serious mistake, followed several other strategic blunders of Adolf Hitler. Given that, this essay reflects a study of primary source material collected from key German commanders, as well as numerous documents collected in 1956 as part of the "Karlsruhe Collection." The focus was to determine where the airlift failed, why it failed, and what could have been done better. Ultimately the failure could be attributed to the lack of a survivable and more capable transport aircraft, difficulties operating out of poorly prepared airfields which were under constant threat from the Red Army, the absolutely miserable weather which frequently prevented any flying at all, enemy action which prevented daylight flights by much of the fleet, supplies which were not ideally suited for airlift, and finally difficulties organizing the airlift at both ends. Many commanders involved knew it was bound to fail and warned Hitler and Paulus, to no avail. In the end, what could have been a tremendous feat ended as tragic folly.