This research quantified the impact that truck mix, distress severity, and climate have on pavement damage and maintenance costs based on Long-Term Pavement Performance (LTPP) pavement sections located in four US states and one Canadian province. A cost analysis was conducted using in-situ records of maintenance and rehabilitation data from 1988 to 2016. The paper presents a detailed methodology to quantify the damage cost per VMT and ESAL-mile for each FHWA truck class. Economies of scale are evident in the cost per ESALmile relative to total pavement loading as segments carrying higher traffic loads require additional maintenance and rehabilitation, however the additional cost for these procedures is outpaced by the increase in traffic resulting in a reduction in the pavement damage cost per ESAL-mile. The cost per ESAL-mile varied from $0.01 to $0.37 per ESAL-mile depending on total loading, a relationship that is accurately modeled (R2=0.97) using the developed power function. Results also show that vehicle class, and thereby the number and distribution of ESALs, significantly impacts the pavement damage cost (p-value= 0.044). The research developed an accurate and robust model correlating pavement damage cost per ESAL-mile to the accumulated number of ESALs during the pavement service life. Transportation agencies can utilize this model to determine a fair and defensible variable compensation for the pavement damage imposed by individual trucks based on the axle loads and configuration.