A 25-year-old previously healthy man presented to our Emergency Department with shortness of breath and epigastric pain after swallowing a boneless chicken nugget one hour prior to presentation. Physical examination revealed epigastric rigidity and tenderness. Serology was normal except for mildly elevated bilirubin and amylase. Computed tomography (CT) scan of the chest revealed a distal esophageal rupture with accompanying pneumomediastinum and left-sided pleural effusion. Treatment was initiated with administration of intravenous fluids and broad-spectrum antibiotics. Subsequently, an esophageal stent was inserted endoscopically in addition to VATS (Video-Assisted Thoracoscopic Surgery) drainage of the left-sided pleural space. This case illustrates an unusual presentation of Boerhaave's syndrome: a rare and life-threatening form of noniatrogenic esophageal rupture most often preceded by forceful vomiting. Our case demonstrates that physicians should maintain an index of suspicion for spontaneous esophageal rupture in patients presenting with shortness of breath and epigastric pain even in the absence of preceding vomiting, cough, or seizure. Additionally, ingestion of boneless, shell-less foods may be sufficient to cause rupture in individuals without underlying esophageal pathology. CT scan of the thorax and upper abdomen should be performed in these patients to rule out this rare and life-threatening diagnosis.