A shock absorbing pin box system includes a first sidewall, a second sidewall, an upper wall, a lower wall, and a kingpin. The first sidewall defines at least a first plurality of apertures arranged in first column, and the second sidewall defines at least a second plurality of apertures arranged in a second column. A plurality of tubes extend from each of the first plurality of apertures and the second plurality of apertures. A plurality of flexible and resilient tubular bushings are received in a corresponding one of the plurality of tubes. A plurality of bolts are received within corresponding ones of the pluralities of apertures of the pin box and the plurality of tubes.