We report a rare complication of right brachiocephalic vein perforation during ultrasound-guided cannulation of the right internal jugular vein (IJV) in a patient with a tortuous common carotid artery (CCA). We suspect that the tortuous CCA displaced the IJV, which caused misplacement of the J-tip guidewire into the subclavian vein. The stiff dilator sheath introduced over the guidewire then perforated the wall of the brachiocephalic vein, causing massive hemothorax. This was diagnosed by videothoracoscopy. Anesthesiologists should be aware of the possibility of guidewire malposition during IJV catheterization in patients with a tortuous CCA.