We investigate different conditions, including the orbital and size-frequency distribution (SFD) of the early Kuiper Belt, that can trigger catastrophic planetesimal destruction. The goal of this study is to test if there is evidence for collisional grinding in the Kuiper Belt that has occurred since its formation. This analysis has important implications for whether the present-day SFD of the cold classical trans-Neptunian objects (TNOs) is a result of collisional equilibrium or if it reflects the primordial stage of planetesimal accretion. As an input to our modeling, we use the most up-to-date debiased OSSOS++ ensemble sample of the TNO population and orbital model based on the present-day architecture of the Kuiper Belt. We calculate the specific impact energies between impactor-target pairs from different TNO groups and compare our computed energies to catastrophic disruption results from smoothed particle hydrodynamics simulations. We explore different scenarios by considering different total primordial Kuiper Belt masses and power slopes of the SFD and allowing collisions to take place over different timescales. The collisional evolution of the Kuiper Belt is a strong function of the unknown initial mass in the trans-Neptunian region, where collisional grinding of planetesimals requires a total primordial Kuiper Belt mass of M > 5 M ⊕, collision speeds as high as 3 km s-1, and collisions over at least 0.5 Gyr. We conclude that presently, most of the collisions in the trans-Neptunian region are in the cratering rather than disruption regime. Given the low collision rates among the cold classical Kuiper Belt objects, their SFD most likely represents the primordial planetesimal accretion.