This illustration showcases the venous drainage pathways from the left side of the body as they cross the midline to the superior and inferior vena cava, highlighting Nutcracker Syndrome and May-Thurner Syndrome, both resulting from venous compression. It also introduces the less commonly described Left Brachiocephalic Syndrome, caused by compression of the left brachiocephalic vein between the aortic arch and sternum, leading to venous congestion.