Crohn's disease (CD) is a type of inflammatory bowel disease (IBD) that affects thousands of Americans, and it is commonly found in individuals aged between 20-30 years. Patients often present with abdominal pain and describe concerns of diarrhea, bloating, and weight loss. In this report, we discuss the case of a 21-yearold man who presented with diarrhea and intermittent hematochezia. He was admitted for a suspected lower gastrointestinal (GI) bleed. An abdominal CT scan demonstrated pancolitis with a mildly distended gallbladder. Subsequent sigmoidoscopy revealed a diagnosis of CD, which was confirmed with a biopsy. Following steroid therapy, the patient reported symptomatic improvement, although his alkaline phosphatase (ALP) levels continued to increase. Magnetic resonance cholangiopancreatography and endoscopic retrograde cholangiopancreatography (ERCP) revealed biliary strictures, which were suggestive of primary sclerosing cholangitis (PSC). This case highlights the importance of not ruling out CD in patients with PSC and understanding the differential clinical outcomes in patients with PSC with ulcerative colitis (UC) compared to those with CD. These differences include variations in colorectal carcinoma risk and severity of symptoms.