Central venous cannulation is a widely used procedure in clinical medicine. Central venous catheters are inserted most often via the internal jugular and subclavian veins. One of the complications is malpositioning of the catheter, and some insertion sites carry a higher risk for that occurrence. We report a case of a malpositioned central venous catheter inserted via the left internal jugular vein in a patient with a ruptured diaphragm. Our objectives were to review the venous anatomy of the chest and the literature reporting malpositioned central venous catheters and to discuss the approach through the left internal jugular vein. Left internal jugular cannulation could carry a higher rate of malposition than reported, and anatomy gives a possible, simple answer. Contrast enhancement, although central venous catheters are radiopaque, is helpful when an approach through the left internal jugular vein is used and difficulties are encountered during insertion.