According to his son Fred, this man first tried smoking just because it was against the rules at West Point

The first Final Jeopardy of 2025 featured a fascinating clue in the category U.S. Presidents, delving into a personal anecdote about a leader known for his remarkable discipline. The clue read:

“According to his son Fred, this man first tried smoking just because it was against the rules at West Point.”

Who is Ulysses S. Grant?

The correct response was Ulysses S. Grant, the 18th President of the United States. This detail from his life provides an intriguing look into the young cadet’s personality, as described by his son, Frederick Dent Grant, in various interviews and recollections.

Ulysses S. Grant entered the United States Military Academy at West Point in 1839. While he eventually became known for his steadfastness and discipline, his time as a cadet revealed moments of youthful experimentation. As his son Frederick Dent Grant recounted, young Ulysses tried smoking cigars during his West Point years, not out of genuine interest but simply because it was against the academy’s regulations.

This small act of rebellion highlights the complexities of Grant’s character. Despite his later reputation for strict adherence to duty and order, this anecdote paints a picture of a young man navigating the same challenges and temptations many face during formative years. Though he initially failed to develop a liking for smoking, the habit would resurface later in his military career.

The Evolution of Grant’s Smoking Habit

While Grant’s early experiments with smoking at West Point were fleeting, his son’s accounts reveal how the habit became ingrained during his military service. According to Frederick, Grant’s smoking became more habitual during the Mexican-American War, when light cigars and cigarettes were widely available. However, it wasn’t until the Civil War that smoking became a prominent part of his public persona.

The turning point came during the Battle of Fort Donelson in 1862. After a meeting with Admiral Foote aboard a gunboat, Grant was seen carrying a cigar. This image of the general, cigar in hand, quickly captured the public imagination. When news of his victories spread, admirers began sending him cigars, leading to an astonishing stockpile of 11,000 cigars. Despite the popular image of Grant as a heavy smoker, his son clarified that he often allowed cigars to burn out and rarely smoked to excess.

Insights from Frederick Dent Grant

Frederick Dent Grant, who served as his father’s aide-de-camp during the Civil War, offered valuable insights into Ulysses S. Grant’s personality. He emphasized his father’s unwavering commitment to duty and his ability to remain calm under pressure. Even during critical moments, such as the surrender at Vicksburg, Grant approached decisions methodically, always striving to do his best.

Frederick’s reflections add depth to Grant’s legacy, portraying him not just as a military leader and president but as a man shaped by his upbringing and values. The anecdote about smoking, shared by Frederick in interviews, serves as a reminder of Grant’s humanity and the relatable challenges he faced.

A Glimpse into Grant’s Legacy

Ulysses S. Grant’s decision to try smoking at West Point, despite its prohibition, offers a unique perspective on his early life. This moment of youthful defiance contrasts with the disciplined and duty-driven leader he became, illustrating the growth and complexity of his character.

The story also underscores the importance of Frederick Dent Grant’s accounts in shaping our understanding of his father’s life. By sharing personal anecdotes, Frederick helped illuminate the qualities that made Ulysses S. Grant a revered figure in American history. From his days as a young cadet testing boundaries to his role as a decisive and resilient leader, Grant’s journey continues to inspire and fascinate