Evaluation of a 50-year-old man with benign but insidious development of chronic superior vena caval obstruction secondary to old pulmonary histoplasmosis is presented. The radiologic evaluation was done in stages to exclude involvement of other disease. Nuclear scintigraphy revealed the superior vena caval obstruction. Anatomical features are compared to dynamic findings using contrast venography, computed tomography, and magnetic resonance imaging to differentiate pulmonary vascular compression from neoplasm and pulmonary embolism. The combination of modalities reveals the character and extent of pathology without extensive interventional procedures.