This article studies why Jonathan Swift’s satirical works are characterized by many critics as uncertain, contradictory, ambivalent, ambiguous, paradoxical, or undecidable. Those words that describe troubling and vexing features can be traced back to Swift’s unique satiric imagination from which originate all the troubling and vexing features. In order to explores the nature of Swift’s satiric imagination, this article analyzes Swift’s attitude towards satire and how he uses satiric imagination. For Swift, satire and the imagination are the two fundamental constituents towards which he showed a deeply ambiguous or ambivalent attitude.