Wednesday, November 23, 1861
My dear Brother Alfred,
I hope this letter finds you in good health and high spirits at White Plains, and I have confidence your education is progressing well. I wanted to share some news that I believe will be of great interest to you.
As you are well aware, I have long regretted the political circumstances that prevented me from entering the United States Military Academy at West Point. It pained me deeply to see the same obstacle standing in your way, my dear brother, for I know how ardently you wish to serve our country in the military. I could not stand idly by and let history repeat itself.
You will recall my friendship with Millard Fillmore. In the hopes of aiding your aspirations, I reached out to him, explaining your desires to attend West Point and the unjust political barriers that have hindered our family. Millard has expressed his willingness to use his connections and influence to advocate for your admission to the academy.
In the coming weeks, Millard will be in contact with key individuals at the academy and within the government, urging them to give your application the fair consideration it deserves. I have the utmost confidence that his efforts, combined with your talent and determination, will secure your place at West Point.
I want you to know, dear brother, that I am immensely proud of you and your accomplishments thus far. My efforts on your behalf are born from the love and admiration I have for you, and from my desire to see you achieve your dreams. It is my hope that by helping to clear the path for you, I can, in some small way, contribute to your future success in the military and beyond.
Please, do not let this knowledge weigh heavily upon you. Continue to focus on your studies and prepare yourself for the challenges that lie ahead. I have no doubt that you will rise to meet them and make our family proud.
I eagerly await your response and any news you may have regarding your application to West Point. Until then, know that you are in my thoughts and prayers.
Your loving brother,
Alfred Gibbs sat in the quiet corner of the library at his school in White Plains, reflecting on the letter he had recently received from George. The letter revealed the efforts George had always taken to help Alfred, this time to gain admission to the United States Military Academy at West Point, despite the political barriers that had once hindered George himself.
As Alfred pondered over the words, he couldn’t help but think of their family’s storied history and the impact it had on their lives. Their great-grandfather, Oliver Wolcott Sr., had been a prominent figure in the founding of the United States, while their grandfather, Oliver Wolcott Jr., served as the second United States Secretary of the Treasury, a judge of the United States Circuit Court for the Second Circuit, and the 24th Governor of Connecticut.
Alfred knew that his grandfather’s shifting political views—from Federalist to Toleration, and finally to Jacksonian—had ultimately played a role in George’s inability to attend West Point. Their family’s connection to the Whig Party had closed certain doors for them, and Alfred couldn’t help but feel a sense of frustration at the unfairness of it all.
Despite the weight of his family’s legacy, Alfred was determined to forge his own path in life. He was proud of his heritage, but he longed to make a name for himself on his own terms. He felt a calling to serve his country as a soldier and warrior, and he knew that attending West Point was a crucial step toward fulfilling that destiny.
As Alfred reread George’s letter, he felt a mixture of gratitude and resolve. He was grateful for the love and support that his brother provided, and for the efforts, George had made on his behalf by reaching out to Millard Fillmore. But he also knew that it was up to him to prove that he was worthy of the opportunity he had been given.
With renewed determination, Alfred would focus on his studies, preparing himself for the challenges that lay ahead. He knew that the road to West Point would be difficult, but he was committed to overcoming any obstacles that stood in his way. In the end, he was determined to show the world, and more to the point, himself that he was more than just the grandson of Oliver Wolcott Jr.—he was Alfred Gibbs, a man who would make his own mark on history.
Alfred couldn’t help but wonder what kind of leader he would become if he were to gain entrance into West Point. As he pondered his potential future, he questioned whether he would be able to distinguish himself from his peers and rise above the expectations placed upon him. Would he be able to display bravery in combat and lead his men with honor, or would the weight of his family’s legacy prevent him from realizing his full potential?
If he was honestly thankful for all his family name had given him, including the schooling he was receiving at that moment, then, why did he feel a twinge of resentment as he considered the privileges he had enjoyed due to his family’s prominence? While he was grateful for the opportunities that came with his heritage, he couldn’t shake the nagging feeling that these privileges had, his entire life, overshadowed his own identity as an individual. Alfred longed to break free from the constraints of his family’s reputation and prove to himself and the world that he was a man of his own making.
As the days passed, Alfred began to engage more with his classmates and instructors, seeking guidance on leadership and the qualities that he knew made for a great soldier. He hoped that by learning from those around him, he could develop the skills necessary to excel at West Point, should he be accepted, and eventually on the battlefield.
In quiet moments, he found himself reflecting on the stories he had heard about his great-grandfather, stories told by his grandfather, Oliver Wolcott Jr. Both men had faced their own challenges and hardships, and yet they had managed to leave their own mark on history. Their resilience and determination inspired Alfred, and he became increasingly made him even more committed to forging his own path.
As Alfred continued to prepare for the future, he began to view his family’s legacy not as a burden, but as a source of strength. He resolved to use the experiences and lessons of his ancestors as a foundation upon which to build his own unique story. With each passing day, Alfred grew more confident in his ability to overcome any obstacles that stood in his way, and he became increasingly determined to create a life and legacy that would be uniquely his own.
Alfred knew that it was up to him to define his own success. He understood that true courage and leadership would be measured not by his lineage but by his actions, his character, and his dedication to his country and fellow soldiers.
As the time for his West Point application drew nearer, Alfred took solace in the knowledge that he was taking control of his own destiny. He knew that the road ahead would be fraught with challenges and uncertainties, but he was committed to facing them head-on and emerging stronger on the other side.
The support of his brother George, the guidance of his instructors, and the lessons of his family’s past all served to inspire and motivate Alfred as he prepared to embark on a new journey, and so, with a mixture of anticipation and resolve, Alfred continued to prepare for his future at West Point, ready to embrace the challenges that lay ahead and to forge his own path.