Cholesterol crystal embolism can be spontaneous or iatrogenic, and it can involve any organ of the gastrointestinal tract, presenting with common gastrointestinal symptoms such as bleeding, perforation, obstruction, and inflammation. It is therefore considered the "great masquerader," requiring a high level of suspicion because the condition is associated with increased morbidity and mortality. We present a 69-year-old man who presented with gastrointestinal bleeding and azotemia. He was found to have cholesterol crystal embolization in the kidney and a duodenal leiomyoma, the latter being an uncommon site to embolize.