The modification of hard jets in an extended static medium held at a fixed temperature is studied using three different Monte-Carlo event generators (LBT, MATTER, MARTINI). Each event generator contains a different set of assumptions regarding the energy and virtuality of the partons within a jet versus the energy scale of the medium, and hence, applies to a different epoch in the space-time history of the jet evolution. For the first time, modeling is developed where a jet may sequentially transition from one generator to the next, on a parton-by-parton level, providing a detailed simulation of the space-time evolution of medium modified jets over a much broader dynamic range than has been attempted previously in a single calculation. Comparisons are carried out for different observables sensitive to jet quenching, including the parton fragmentation function and the azimuthal distribution of jet energy around the jet axis. The effect of varying the boundary between different generators is studied and a theoretically motivated criterion for the location of this boundary is proposed. The importance of such an approach with coupled generators to the modeling of jet quenching is discussed.