This paper reports on finite element analysis techniques that may be applied to the study of circular hollow structural sections and related bearing connection geometries. Specifically, a connection detail involving curved steel saddle bearings and a Structural Tee (ST) connected directly to a large-diameter Hollow Structural Section (HSS) truss chord, near its open end, is considered. The modeling is carried out using experimentally verified techniques. It is determined that the primary mechanism of failure involves a flexural collapse of the HSS chord through plastification of the chord wall into a well-defined yield line mechanism; a limit state for which a shell-based finite element model is well-suited to capture. It is also found that classical metal plasticity material models may be somewhat limited in their applicability to steels in fabricated tubular members.