Contarini’s Syndrome is a rare clinical entity characterized by bilateral pleural effusions arising from different underlying etiologies. We report a case of an 80-year-old male presenting with dyspnea, cough, abdominal pain, and fever. Imaging and diagnostic thoracocentesis revealed a right-sided exudative pleural effusion due to bacterial empyema (Staphylococcus aureus) and a left-sided transudative effusion associated with hypoalbuminemia and chronic liver disease. The patient was managed with targeted antibiotics and therapeutic thoracocentesis. This case underscores the importance of considering bilateral thoracentesis in patients with atypical clinical or radiological findings and highlights the diagnostic value of Hickam’s dictum in differentiating dual pathologies. Recognition of Contarini’s syndrome is essential to avoid misdiagnosis and ensure appropriate treatment.