Orbital evolution is a critical process that sculpts planetary systems, particularly during their early stages where planet–disk interactions are expected to lead to the formation of resonant chains. Despite the theoretically expected prominence of such configurations, they are scarcely observed among long-period giant exoplanets. This disparity suggests an evolutionary sequence wherein giant planet systems originate in compact multiresonant configurations, but subsequently become unstable, eventually relaxing to wider orbits—a phenomenon mirrored in our own solar system’s early history. In this work, we present a suite of N-body simulations that model the instability-driven evolution of giant planet systems, originating from resonant initial conditions, through phases of disk dispersal and beyond. By comparing the period ratio and normalized angular momentum distributions of our synthetic aggregate of systems with the observational census of long-period Jovian planets, we derive constraints on the expected rate of orbital migration, the efficiency of gas-driven eccentricity damping, and typical initial multiplicity. Our findings reveal a distinct inclination toward densely packed initial conditions, weak damping, and high giant planet multiplicities. Furthermore, our models indicate that resonant chain origins do not facilitate the formation of Hot Jupiters via the coplanar high-eccentricity pathway at rates high enough to explain their observed prevalence.