In this paper, casting and winding dynamics of hyper-flexible manipulator is analyzed. Casting and winding with hyper-flexible elements like strings, ropes or wires should be a useful operation to capture a distant target object. A multi-link system connected by passive non-elastic joints is employed as a discrete dynamic model of hyper-flexible systems. Casting and winding dynamics is analyzed with the multi-link model. Casting and winding motion can be divided in several phases as casting, contacting, winding and capturing. This paper focuses on the casting motion suitable for winding onto a round target object. Simulations are executed to clarify a suitable casting motion to realize a good and firm winding. Several criteria as contact position, contact velocity, slack length and looseness on the target are employed to evaluate the winding results.