Short story is one of the popular literary genres in today’s world. Anton Chekhov is considered one of the greatest short story writers ever. Like all humans, he was not always wise in all phases of his life, but he was wiser than most of the Russian intelligentsia. The question Readers and writers often ask is "why?" The simplest answer seems to be that he revolutionized the short story by transforming the narrative. He made short stories appear agonizingly, almost unbearably lifelike. Chekhov abandoned the beginning-middle-and end-plot that was so popular in his time. By refusing to judge his characters, and by not striving for a climax or seeking neat narrative resolution, he completely turned the short story around. Imagery is one of the key tools of his short stories. Chekhov’s most outstanding wisdom characteristics were his humility, his tolerance, and his compassion. His compassion was not only for his contemporaries of various classes, especially the unfortunate, but also for future generations. This study has a strong effort and attempt to focus Chekhov’s contribution in world literature, especially in short stories by exploring imagery.