The triad of acute osteomyelitis, deep venous thrombophlebitis, and septic pulmonary embolism is a rare, but life-threatening syndrome in children that requires prompt recognition and treatment. We report two cases of acute osteomyelitis complicated by septic thrombophlebitis and pulmonary emboli. Both patients required operative drainage to remove the septic focus. Recognition of any one component of the triad should prompt a search for the other associated disorders. Aggressive management with early antibiotic administration, anticoagulation, and surgical debridement can be life saving.