It is well known that Western Europe has enjoyed a longstanding fascination among scholars and students. So much so that calls to move beyond the region towards a global focus in academia are increasing daily. Yet, much of Western Europe's history beyond England, France, and Germany remains unexplored. Spain has enjoyed a resurgence of interest, but Portugal has largely been ignored. Indeed, many do not even consider the two Iberian nations and their entangled histories with Islam and North Africa as part of Europe proper despite their many contributions to the western tradition. Even more isolating is the fact that much of the recent effort at recovering the Portuguese past remains confined to studies within the Portuguese language. This piece, therefore, aims at tackling both lacunae by examining the deeds and achievements of an important but forgotten hero of an often-forgotten nation, Geraldo the Fearless. Geraldo the Fearless was a marauding knight who lived on the edge of conflict between the young Kingdom of Portugal, the Spanish kingdom of Leon, and the Muslim realms with his band of motley knights. Working with the King of Portugal, Geraldo launched an offensive campaign against the neighboring Christian and Muslim kingdoms, rapidly conquering many cities in the Muslim South, causing new alliances, and creating political turmoil in a bid to conquer Badajoz. Later, Geraldo continued his mission in Morocco, where he attempted to take possession of several cities with the assistance of the Berber tribes for the Kingdom of Portugal. This article utilizes numerous Portuguese, Spanish, Latin, and Arabic sources to methodically gather the many pieces required to recreate a comprehensive view of Geraldo and his life. Moreover, this research, by employing additional evidence, attempts to infer events and fill historical gaps. By creating a clear narrative of the life of Geraldo, it then becomes possible to fully see his influence on Portuguese history as a critical lens into the forming of the Portuguese Empire and its later imperial expansion. Had Geraldo succeeded in his designs, the borders of Spain and Portugal would have been drastically different; furthermore, if he had succeeded in Morocco, Portuguese expansion out of Europe would have begun nearly 240 years earlier. An earlier Portuguese conquest of North Africa would likely have tipped the balance of power in the Iberian Peninsula, which could have elevated Portugal to a more prominent role among the other European monarchies. As intriguing as it is to consider hypotheticals, there is no way to know what would have occurred for sure. What is certain is that Geraldo the Fearless rose from obscurity and left an indelible mark on Luso-Hispanic history before disappearing once again.