A system and method for end-to-side anastomosis to an anatomical passageway is disclosed. The system and method are particularly useful in coupling an LVAD pump to an aorta. The system and method include using a tubular graft member having a skirt flange that engages the side of the aorta, a seating assembly and a flanged stent for securing the tubular graft to the side of the anatomical passageway. An assembly for creating an opening in the side of the anatomical passageway and an assembly for delivering the tubular graft is also disclosed.