The unique comparison between Jonah and the Son of Man in the First Gospel has been notoriously difficult for several reasons. First, “three days and three nights” cannot be fitted into the interval of Jesus’ burial in the tomb from Friday evening to Sunday morning; second, the resurrection of Jesus, which is understood by some as “the sign of Jonah,” was not witnessed by “an evil and adulterous generation,” but only by believers in Christ; third, an above sea-level tomb like the one that contained Jesus hardly qualifies as “the heart of the earth” in the sense of subterranean depth; and fourth, interpreting “the heart of the earth” literally as Sheol still does not resolve the chronological problem. However, the enigma of the Jonah saying unravels with a shift in perspective. This article will recognize that shift and propose a new understanding of this passage.