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How far can an individual’s influence and decisions affect the economy of a province? This paper endeavours to argue, through an individual level of analysis of Joseph R. Smallwood, for the influence of his 23-year reign on the political economy of Newfoundland. Smallwood’s intentions for Newfoundland’s economic development were of noble cause, but because of his urgency to “develop or perish” the plans just perished. Smallwood’s strong personality and nationalistic perspective led him to make irrational decisions that may have seemed potentially beneficial to the province in his mind, and in theory, but with a habit of going into a plan head strong and under researched, what started as an economically beneficial strategy would incur even more debt on the province.