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Few American presidents have earned a legacy quite as prolific and inspiring as that of Theodore “Teddy” Roosevelt. His bold, charismatic leadership style and his aggressive attitude toward government action resulted in an almost mythic persona that persists to this day. My respect for TR stems from a young age, because the house in which he spent thirty-four years of his life, Sagamore Hill, is located in my hometown of Oyster Bay, NY. Naturally, his legacy was ever-present. 

Later in life, I had the privilege of meeting TR’s most famous biographer, Edmund Morris. After having read Theodore Rex, the second volume of Morris’ trilogy, I discovered that the brilliant researcher and Pulitzer Prize winner happened to be the upstairs neighbor of my father’s good friends. A discussion with Morris and my longstanding book club was arranged, and it afforded me a deeper understanding of Roosevelt beyond the bully pulpits and teddy bears. Just before the book club disbanded for the night, my father presented Morris with a watercolor he had painted of Sagamore Hill. A parting gift between two individuals with prolific creative careers.

Mark Fasciano and friends meet TR biographer Edmund Morris

My meeting with Edmund Morris pictured here.

When I look to the past to learn from the core beliefs and practices of history’s most influential leaders like TR, I maintain that it’s just as important to analyze their failures as their successes. In doing so, we can pay well-deserved homage to inspirational leaders while still acknowledging their human limitations.


Growth & Development

As president, Theodore Roosevelt was constantly pushing the limits of his individual growth. He would have argued that true leaders are made, not born. He understood that the path to effective leadership was an ongoing process, one which was dependent in large part on self-reflection and self-improvement.

Individuals who occupy positions of leadership must avoid complacency, he insisted. Satisfaction with having met particular goals is a good sign, but leaders should strive to continually develop themselves in productive, meaningful ways so that they can effectively serve others and gain their trust.



Roosevelt’s success hinged in large part upon his passion for his work.The key to success (or one of several on the keyring of success) is allowing passion to run through everything that you start—every painting, every project.

TR’s passion was rooted in his values. Many of his executive decisions revolved around the values of fairness, equal opportunity, and economic growth. With such lofty ideals in mind, Roosevelt was able to enact major changes in the government’s relationship to big business, the role of the president as a whole, environmental conservation, and foreing affairs. 

Roosevelt directly oversaw the Panama Canal negotiations, and he intervened in the conflict between Venezuela and Santo Domingo for the sake of regional stability, His desire for national success and international peace guided him to make bold decisions that paid off tenfold.



Roosevelt’s impressive reputation and successful record can also be attributed to his masterful charisma and relatability. Despite holding such high-level positions as governor, Vice-President, and President throughout his career, he made a point to engage with the people, as well as with other politicians and media-makers, cultivating a bond of mutual communication and trust. For Roosevelt, leading the nation was never just about instituting political change; it was about understanding the needs and desires of the public, demonstrating genuine enthusiasm towards positive change, and connecting with others to understand and represent widespread opinion.


Theodore Roosevelt’s life and presidency validated my belief that collective success is a consequence of individual betterment. By embracing a growth mindset and multifaceted interests, while communicating consistently and authentically with those we serve, we can emulate Roosevelt’s leadership prowess in our daily lives.