Xanthogranulomatous cholecystitis (XGC) is difficult to diagnose preoperatively because it often mimics gallbladder cancer. We present a case of a 64-year-old Caucasian male who presented with multiple intrahepatic abscesses, left portal vein and segmental right hepatic arterial thrombosis suspicious for extrahepatic cholangiocarcinoma who ultimately underwent an extended left hepatectomy and was noted to have XGC on final pathology. This case presents a new challenge in diagnosing XGC prior to final pathology results given the unique left portal vein, and later, right anterior portal vein thrombosis and occlusion. XGC should be in the differential diagnosis when diffuse gallbladder wall thickening is associated with involvement of biliary and vascular structures. While diagnosing these cases can be challenging, increased awareness of varied involvement of the liver and hilar structures associated with this diseases process may aid in the selection of the most appropriate surgical techniques.