We present an unusual case of hypertrophic cardiomyopathy complicated by mitral regurgitation resulting from chordal rupture with flail posterior mitral leaflet. The diagnosis was suggested by the presence of an anteriorly directed mitral regurgitation jet on transthoracic color flow imaging, in addition to the typical posterolateral-lateral jet caused by systolic anterior mitral motion. The flail posterior leaflet was confirmed by transesophageal echocardiography, and the patient underwent mitral valve repair in addition to myectomy. This combination of hypertrophic cardiomyopathy and flail mitral leaflet usually requires surgical intervention, and prompt diagnosis is important. The presence of an anteriorly directed mitral regurgitant jet should always raise suspicion of posterior mitral leaflet abnormality.