Samso was a writer and politician in Northern Song Dynasty, whereas Yoon-gi was a writer from the Nam-in group (then political party) in the mid-18th century of Joseon Dynasty. They both left a relatively large amount of historical essays, due to historic and personal causes. A historical essay is usually included in the genre of criticism, rather than history, and contains allegories about contemporary affairs through historic criticism. The reason why the two men stuck to the genre was the system of national exam (called "Gwa-keo"). They had to practice their skills to compose historical essays to show their historic knowledge, literary talents and statesmanship. However, not all historic essays were created for the purposes. In particular, while Samso`s essays focused more on contemporary affairs, Yoon-gi`s ``inadvertently`` let his lament out. They once dealt with the same person in their essays, which could be examined from comparative perspectives. For sure, both essays show common traits, like in-depth discussions about king`s machinations and humanism. However, Samso focused on success and failure by discussing how the king govern his nation, whereas Yoon-gi, who was trained as a student of Sung Gyun Gwan (then University) for 20 years but ended up with no power, focused on allegories about the king himself, out of the writer`s expectations about the king`s personality and statesmanship. Yoon-gi`s criticism failed to show the king`s strategic thinking and practice or his commitment to the people`s livelihood, which Samso described well, but tried to present a new type of criticism about a person by looking into the person`s psychology and reading between lines and by deciding humanism as a criteria of statesmanship. Considering that a king should understand what his subordinates think and have humanism, Yoon-gi`s essays demonstrate some aspects of the era.