Cholesterol emboli syndrome is a rare syndrome of tissue ischemia and necrosis caused by the embolization of cholesterol crystals from atherosclerotic plaques, leading to vascular occlusion. This report documents a case of cholesterol emboli syndrome in a 72-year-old male with multiple cardiovascular risk factors including end-stage renal disease, atrial fibrillation, hypertension, hyperlipidemia, and type 2 diabetes. We describe this patient's atypical presentation with upper extremity rather than lower extremity digital ischemia as a presenting sign and significant subsequent functional decline exacerbated by his comorbidities. In addition, we review the available treatment options for cholesterol emboli syndrome, including medical management, and discuss the risks of surgical intervention, including death and limb loss. This study concludes that atypical manifestations of cholesterol emboli syndrome can result in particularly morbid outcomes due to loss of fine motor skills in their hands, reducing patients' independence and exacerbating other medical conditions.