24. Grover Cleveland – 144
In 1884, Grover Cleveland achieved a significant milestone as the first Democrat to win a presidential election since the Civil War’s end. Surprisingly, this victory was not the only one in his political career. Cleveland famously left the White House after his first term in 1889, but he made a remarkable return and served as president once again in 1893. Despite facing financial hardships that forced him to end his formal education at the age of 16, Cleveland persisted in part-time studies and eventually passed his bar exams, paving the way for his future leadership.