The hero of the play, Ivan Petrovich Voynitsky, or Vanya (a name so common as to be equivalent to "Jack" or "Johnny" in English) is a bitter, aging man who has wasted his life in toil for his brother-in-law Serebryakov. Functioning as the play's misanthrope, he offers a number of humorous caricatures of those around him and is thus privileged with a certain bitter insight, though one that lacks the deliberation of Astrov. Put more directly, he is the character who most explicitly points out the miserable nature of the other characters' lives.

Vanya is obsessed with his wasted years and the thought of what might have been—a major object of this jealous obsession being the professor's wife, Yelena. As Yelena notes, this obsession betrays a certain "destructive" impulse in his character. One also wonders if it might involve a hopeless fantasy to liberate them both from their bondage under Serebryakov.

Throughout the play, Voynitsky will find himself silenced, dismissed, and rejected. He suffers two major humiliations, both in Act III. First, he returns with a bouquet of roses for Yelena, only to witness her near-seduction by Dr. Astrov, and second, he fails to shoot his "bitterest enemy," Serebryakov, in the next scene. This botched murder is also the play's farcical pseudo-climax, as Voynitsky misses his foe twice at point blank range. Voynitsky thus emerges as less a tragic hero than a pathetically broken man.

Reduced to nothing by the fourth act, Voynitsky falls into a terrible depression and throws himself into his drudgery to keep his misery at bay. He speaks of madness, his dread before the empty years to come, and hopelessly dreams of a new life. In the end, he will find solace in no one—not his mother (who defers to the professor in all matters), nor the embittered Astrov, nor his niece, Sonya, who urges him to look toward death for peace.