This is an essay from my undergraduate years at the London School of Economics. I thought maybe someone could use it, in whatever way. Beware academic language.
What is success? According to the Oxford Dictionary, it is the outcome of an undertaking, specified as achieving or failing its aims. In order to determine how successful Columbus really was, the outcome of his undertakings must be examined. One would instantly wonder how Columbus can even be considered successful when his original aim of reaching and finding a shortcut to India was not achieved. Although he did not find what he was initially looking for, the outcome of his undertaking was still positive by discovering a whole new landmass. Fernandez-Armesto reveals the historical debates on Columbus.
First, some scholars believe that he was not what he seemed and “his plan for an Atlantic crossing concealed some secret objective” . However there is a lack of evidence to support that and its mostly speculation. Second, Fernandez-Armesto indicates that some scholars use “imaginative reconstructions of what Columbus must have been thinking or doing at moments when the sources are silent.”  However, we are well-informed about Columbus because he has left many traces and writings of his own. Third, many scholars think of Columbus as a uniquely single-minded figure. According to Armesto this is false because he was plagued by doubts, his sense of divine purpose grew gradually and his geographical ideas took shape slowly. According to Cecil Jane his objective was undefined and confused. He acted secretively and his purpose was vague. “He invited the sovereigns to embrace an enterprise, the exact nature of which he refused to define.” 
Further the degree of his success is dependent upon how one sees and perceives him. His life as an explorer was very different to his life as a colonial governor. In addition, his contemporaries interpreted Columbus’s success in a different way than people do today with the benefit of hindsight by which the ramifications of his discovery are much more apparent. When Columbus was still alive, most of his contemporaries could not possibly foresee the chain of events that his discovery in 1492 would trigger. “It seemed as though Columbus might be doomed to oblivion… partly because the true significance of his achievement was itself so hard to grasp.”  Similar to a coin, there were two sides to Columbus.
First, I will focus on Columbus as an explorer and analyze whether his undertaking as an explorer was successful or not. Further I will focus on Columbus as a colonial governor and analyze his governance on Hispaniola. Then we can put his successes and failures in perspective and determine how successful his undertakings really were.
Columbus was successful as an explorer. Not for conceiving an idea, but for turning an idea into reality. Although there were others who were passionate about exploration and discovering and mapping the world, their ideas never materialized. The few who had the courage to take the risk of exploration were often not very successful in finding anything. “In 1487 the Fleming Ferdinand van Olmen set out with two ships from the Azores… he seems to have misjudged the prevailing winds, sailed off into the mists and was never heard of again.”  The fact that Columbus discovered something should be taken into account when determining whether he was successful or not.
Thus, it cannot be a compelling argument against Columbus to render him unsuccessful simply because he did not find what he was looking for. In fact, by discovering America, he indirectly found what he was looking for. Columbus was looking for a westward route to India in the first place, because the Ottoman Empire had cut off the land routes to India. As a result, European traders looked for new ways to access lucrative spices such as pepper. Thus, Columbus’s aim was to find a new trading route and by stumbling upon the Americas, he ensured a new trading route not in the short-term but at least in the long-term.
Unfortunately Columbus never realized that fact by himself, as Abulafla notes he “was obsessed with the certainty that he would discover a route to Asia.”. Parry further notes that “he claimed, and believed until his death , that he had found islands lying off the coast of Eastern Asia, and possibly part of the mainland, too.  He discovered America because he was driven by his passion to find a westward trade route to India, but tenaciously sticking to his original aim and not recognizing and embracing his new discovery, would later tarnish his success.
His background was humble and his father was a middle-class wool weaver. Columbus thus belonged to an artisan class, but in his heart he was an adventurer. He learned the ropes of a sailor when he was young while craving for the sea. He began to read and educate himself, and slowly established connections between the Mediterranean region and the Atlantic and undertook many commercial journeys before his first voyage to the Americas.
When he eventually discovered parts of the Americas on his first voyage in 1492, one could easily have said that someone else would have discovered it eventually. The validity of the argument can be tested by considering the following counterfactual. What if Columbus had never lived? Phillips indicates that undoubtedly someone else would soon have taken the step, even if Columbus had never lived. While it seems likely that the Americas would have eventually been discovered by someone else, this way of thinking would discredit any human discovery or invention.
Philips’s assumption is based on the notion that the right conditions were created and for that matter anyone could have discovered the Americas since many other men had similar ideas, dreams of discovering the world and establishing new trading routes. While the environment in the later part of the 15th century was conducive for exploration, Philips does not take into account that it takes more to turn an idea or conception into reality.
Columbus was at the right time and the right place, and luck certainly played a role. The fact that ships and the capacity for such journeys existed certainly contributed to Columbus’s success. Isaac Newton once noted that he as a scientist has seen further only by standing on the shoulders of giants and the same is true for Columbus. As an explorer he has learned from Marco Polo’s literature and Paulo Toscanelli’s letter to Fernao Martins which served him as a blueprint in the early stages. Eventually Columbus turned his idea into reality because of his desire and persistence.
Although he was not the first to try, he distinguished himself by being the first successfully crossing the Atlantic Ocean. Many failed mobilizing resources by lacking experience and persistence to persuade the crown and investors to finance their venture. Columbus, as many other before him, faced many rejections. For example, when he went to Portugal, England, and France, neither of them would fund him. Spain was reluctant at first, as well. Although the Crown thought the undertaking was interesting, they did not find it worthwhile. However after appealing to the queen’s religious spirit, Isabella agreed to partly finance his ventures. Finally he had persuaded the Spanish to support his vision. When Columbus further secured funds by investors from Seville and Valencia, he began to build three ships, Nina, Pinta and Santa Maria, recruited men and set sail in 1492.
The subsequent journey which led to his discovery of the Americas was determined not only by luck, but also by having the right equipment, people, experience and skills. In fact, it is hard to single out any one factor that led to the discovery. However as soon as Columbus returned to Spain from his first voyage, some people were skeptical and thought what he achieved could not be rendered successful. Italian historian and traveler Girolamo Benzoni describes a situation in which Columbus joined Spanish nobles for dinner and one of them said:
Sir Christopher, even if your lordship had not discovered the Indies, there would have been, here in Spain which is a country abundant with great men knowledgeable in cosmography and literature, one who would have started a similar adventure with the same result. Columbus did not respond to these words but asked for a whole egg to be brought to him. He placed it on the table and said: My lords, I will lay a wager with any of you that you are unable to make this egg stand on its end like I will do without any kind of help or aid. They all tried without success and when the egg returned to Columbus, he tapped it gently on the table breaking it slightly and, with this, the egg stood on its end. 
Once he had discovered America, anyone knew how to get there. His passion for exploration when he was very young, and his persistence for not giving up when investors rejected him, were early signs that Columbus would succeed as an explorer. Besides, although few expected another large continent in the ocean, there was nonetheless a risk associated for undertaking the voyage and as a result Columbus deserves credit for taking that risk. From a Eurocentric point of view, he was the first to discover the Americas and thus as an explorer he was very successful.
Upon his return, the Crown endowed him with privileges as negotiated before his journey such as extensive commercial and financial rights. For example, revenues in terms of one tenth of all gold, pearls, and other cargoes. Further he was given the title of Admiral of the Ocean, as well as Viceroy and Governor General in the islands that he discovered and above all his privileges were perpetual and last forever. By granting Columbus hereditary titles, entry into the gentility and a share of the profits, the Crown at first considered him successful although they also expected him to return profits from his discoveries.
Columbus’s subsequent voyages would tarnish his early success as an explorer and he would prove inept to govern the islands that he had discovered. He understood that his future success was directly linked to the profitability of the land that he had discovered, but he also feared that his discoveries would not yield quick profits. So he exaggerated the amount of resources that were found and painted an ideal picture that depicted anything but reality. He basically invented riches that did not exist. As a colonial governor he indeed failed. “Great explorer, and sea commander, brilliant navigator though he was, Columbus had neither the experience nor the temperament of a successful colonial governor.”  In fact, his governance was plagued with disappointments.
Columbus would concentrate on the exploitation of Hispaniola and use the natives as a means to extract gold while holding other men responsible for its collection. However that system would not last very long. He overestimated the capacity of the natives to supply labor. Besides the natives perceived the Spanish as a threat to their existence and would certainly not have considered Columbus successful. “The natives greeted the return of Columbus with apprehension.”  In Columbus’s journal he writes about the natives: “they will make good servants of good understanding as I see that they repeat promptly what is said to them and I think that they will easily become Christians.” 
Eventually “the system of native tribute collected through the chiefs had broken down irrevocably with the destruction of the social structure of the central part of the island.”  There were also disputes between the Crown and Columbus because Columbus’s intention was to establish a trading route while Isabella and Ferdinand wanted the new discoveries to be colonized and yield profits.
Columbus did not succeed as a colonial governor but as an explorer. “He felt more deeply, perhaps, the interruption of his work as an explorer — more frustration of his continuing efforts to get to the fabled Orient.”  However the various problems on Hispaniola prevented Columbus from exploring further. In the seven years that Columbus would govern, he promised much but delivered little.
As a leader, he failed to keep the men loyal to him and he could not assign a proper task to many that he brought. He managed to alienate his own people rather than having them on his side. For example, when Bobadilla and Roldan triggered revolts, there was little that Columbus could do. Columbus did not have the ability to improve himself as a leader and adapt to changing circumstances. Additionally he believed strongly in God and thought his journey was dependent on God’s blessing.
“He was, he professed, divinely elected to execute a part of God’s plan for mankind, by making the gospel audible in evangelized parts of the earth.”  Further, when he thought that he was temporarily out of favor with God, he justified using the natives as slaves to extract more gold. In general, when there were problems, he blamed others but never himself when in fact most of the problems can be traced to human error caused by his own mistakes.
Columbus was both a success and a failure, and it depends what vantage point is used to look at his achievements and undertakings. The ambition that drove him and never allowed him to enjoy his success did not bring him happiness in the end. “His sights were always fixed on unmade discoveries, unfinished initiatives, imperfect gains, and frustrated crusades. Instead of being satisfied with his achievements, he was outraged by his wrongs.”  As Armesto highlights he “died a magnificent failure: he had not reached the Orient. His failure enshrined what, in the long term, came to seem a greater success: the discovery of America.” 
However we cannot blame his contemporaries for not considering him successful, because the crossing from Europe to the New World was simply beyond most people’s conception. Nonetheless, his success as an explorer and his discovery of America remains his one single victory that outshines all his other failed undertakings. “A weaver’s son had died titular Admiral, Viceroy, and Governor; that he should have become the founder of an aristocratic dynasty and have established a claim to fame which has made and kept his name familiar to every educated person in the western world.”  Columbus’s merits need to be judged not only by his accomplishments but also by his contribution to mankind.
Columbus was far from perfect as a human being, and was seen more heroic than he really was. For example, on Columbus Day successful achievements are rather overemphasized and his failures overlooked. Thus, when drawing a picture of Columbus, one has to take into consideration both his virtues and vices. In the end how successful he really was depends on what vantage point is taken to judge his successes and failures both as an explorer and colonial governor.
Armesto, Felipe (1991) Columbus. (Oxford: Oxford UP, 1991)
Benzoni, Girolamo (1565) History of the New World. (London: Hakluyt Society, 1857)
Elliot, J.H. (1970) The Old World and The New. (Cambridge: Cambridge UP, 1998)
Hawker, Sara and Soanes.(2006) Oxford English Dictionary. (Oxford: Oxford UP
Livermore, H.V. (1957) ‘Portuguese Expansion’, in The New Cambridge Modern History,
Vol.1 (Cambridge: Cambridge UP)
Parry, J.H (1957) ‘Spaniards in the New World’, in The New Cambridge Modern History,
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Phillips (1992) The Worlds of Christopher Columbus. (Cambridge: Cambridge UP, 1992)
Sauer, Carl (1966) The Early Spanish Main. (Berkeley: University of California Press, 1981)
 “Success”. Oxford English Dictionary. 2nd ed. Oxford UP, 2006. Print.
 Fernandez-Armesto, Columbus, preface
 Fernandez-Armesto, Columbus, preface
 Fernandez-Armesto, Columbus, x
 Sauer, The Early Spanish Main, 15
 Elliot, The Old World and the New, 10
 Abulafla, The Discovery of Mankind, 12
 Abulafla, The Discovery of Mankind, 12
 Parry, The New Cambridge Modern History, 430
 Phillips, The Worlds of Christopher Columbus, 98
 Girolamo, History of the New World, 10
 Parry, The New Cambridge Modern History, 432
 Sauer, The Early Spanish Main, 72
 Sauer, The Early Spanish Main, 32
 Sauer, The Early Spanish Main, 98
 Fernandez-Armesto, Columbus, 151
 Fernandez-Armesto, Columbus, x
 Fernandez-Armesto, Columbus, 192
 Fernandez-Armesto, Columbus, 92
 Fernandez-Armesto, Columbus, 184