Systems and methods are disclosed herein that generally involve a double pinch criterion for optimization of regenerative Rankine cycles. In some embodiments, operating variables such as bleed extraction pressure and bleed flow rate are selected such that a double pinch is obtained in a feedwater heater, thereby improving the efficiency of the Rankine cycle. In particular, a first pinch point is obtained at the onset of condensation of the bleed and a second pinch point is obtained at the exit of the bleed from the feedwater heater. The minimal approach temperature at the first pinch point can be approximately equal to the minimal approach temperature at the second pinch point. Systems that employ regenerative Rankine cycles, methods of operating such systems, and methods of optimizing the operation of such systems are disclosed herein in connection with the double pinch criterion.