The best known model for numerically simulating the hysteretic behavior of various structural components is the bilinear hysteretic system. There are two possible mechanical formulations that correspond to the same bilinear model from a mathematical viewpoint. The first one consists of a linear elastic spring connected in series with a parallel system comprising a plastic slider and a linear elastic spring, while the second one comprises a linear elastic spring connected in parallel with an elastic-perfectly plastic system. However, the bilinear hysteretic model is unable to describe either softening or hardening effects in these components. In order to account for this, the bilinear model is extended to a trilinear one. Thus, two trilinear hysteretic models are developed and numerically tested, and the analysis shows that both exhibit three plastic phases. More specifically, the first system exhibits one elastic phase, while the second one exhibits two elastic phases according to the level of strain amplitude. Next, the change of slope between the plastic phases in unloading does not occur at the same displacement level in the two models. Furthermore, the dissipated energy per cycle in the first trilinear model, as proven mathematically and explained physically, decreases in the case of hardening and increases in the case of softening, while in the second trilinear model the dissipated energy per cycle remains unchanged, as is the case with the bilinear model. Numerical examples are presented to quantify the aforementioned observations made in reference to the mechanical behavior of the two trilinear hysteretic models. Finally, a set of cyclic shear tests over a wide range of strain amplitudes on a high damping rubber bearing is used in the parameter identification of the two different systems, namely (a) trilinear hysteretic models of the first type connected in parallel, and (b) trilinear hysteretic models of the second type also connected in parallel. The results show that the complex nonlinear shear behavior of high damping rubber bearings can be correctly simulated by a parallel system which consists of only one component, namely the trilinear hysteretic system of the first type. The second parallel system was not able to describe the enlargement of the dissipated hysteresis area for large strain amplitudes.