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Dante Tieri, the billionaire benefactor of Chicago’s most exciting bash for military personnel, is also one of the city’s most sinful single men. Italian, driven, and unapologetically rich, Dante is in full control of his world—until his world is turned on its axis in the middle of his own party.

Lieutenant Celina Kouris, a Navy JAG officer, couldn’t care less about Dante’s clothes, looks, or bill...