Compression of the left renal vein between the aorta and the superior mesenteric artery has been termed the nutcracker syndrome. Obstruction of left renal vein outflow results in venous hypertension with the formation of intra- and extrarenal collaterals and/or the development of gonadal vein reflux. To date, a variety of clinical symptoms due to mesoaortic compression of the left renal vein (nutcracker syndrome) have been described. It is not known what pathophysiological variables play a role in the different clinical manifestations of nutcracker syndrome. We report two patients representing the two different forms of the condition. In the first, hematuria and left flank pain resolved in a young man after successful renocaval reimplantation. In the second, symptoms of pelvic congestion due to pelvic varices improved in a middle-aged woman after successful embolization of the gonadal vein and pelvic collaterals. This report reviews the pathophysiology, presentation, diagnosis including radiographic findings, management options, as well as the current literature on nutcracker syndrome.