Nutcracker Syndrome (NCS) is a rare cause of pelvic venous congestion syndrome and is secondary to either compression of the left renal vein (LRV) in its normal anatomic position by the Superior Mesenteric Artery or, more infrequently, when the LRV is in a posterior aortic position being compressed by the aorta against the spine. Often difficult to diagnose, NCS is classically characterized by chronic left flank and left lower quadrant abdominal pain, pelvic congestion syndrome, lower extremity edema and venous varicosities. We present a unique case of NCS in a 30 year old woman with a 3 year history of chronic pelvic pain and venous congestion. A transperitoneal approach was utilized to isolate and mobilize the posterior LRV and transpose it to an anterior position, thus relieving the compression. The left gonadal vein was also ligated.