What were some of the challenges facing the Holy Roman Emperors during the Middle Ages?
What errors in judgment, if any, did they make, and what alternatives might they have pursued?
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Another challenge was simply geography. Before the Empire, there really wasn't much infrastructure connecting different regions. The Empire sought to connect their lands with things like roads and buildings, but this was a difficult process. They didn't have the kind of technology that would exist in the years to come. It was difficult to control such a vast region that was separated by various geographic constructs. Actually, we can credit the Empire for much of the roads and other changes that would later help the regions of the Middle Ages develop.
The major challenge that these men faced was keeping a large empire together in circumstances that were not suited for large empires. The emperors didn't have the kind of military power or the legitimacy needed to keep their whole empire in line so they needed to rely on local nobles. These nobles would often get to the point of wanting power for themselves and therefore going against the emperors.
At various points, the medieval Holy Roman Emperors were pretty effective at securing noble support, as much as any other medieval monarchs, anyway. What they struggled greatly with was the growing power of the papacy. This was a far greater threat to their legitimacy than nobles. With papal reform in the eleventh century, popes began to challenge kings' right to lay investiture- appointing bishops to their offices. This was resolved, basically in favor of the popes, at Canossa, where HRE Henry IV begged forgiveness by kneeling in the snow before Pope Gregory VII. It was this controversy that basically emboldened nobles to seek to gain more autonomy, by controlling the election of the emperor. This is why the two most famous HRE's of the medieval period, Frederick Barbarossa and Frederick II, attempted to conquer the Italian peninsula. Frederick II was actually excommunicated for his campaign.
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