An article of footwear comprising: an upper extending from a first end in a forefoot region to a second end in a heel region and including heel side panels and a heel panel wrapping around a posterior end of the footwear and connecting the heel side panels; a sole structure attached to the upper and including a posterior end extending beyond the second end of the upper, the sole structure including a bladder having a first portion disposed between the second end of the upper and the posterior end of the sole structure, the sole structure including a footbed and a bolster extending from the footbed at the posterior end; and a support system connecting the sole structure to the upper, the support system including a buttress including a stanchion formed at a first end and a heel clip formed at a second end, the stanchion including a base portion attached to the bolster and a neck portion extending upwardly from the base portion to a distal end adjacent to the heel panel of the upper, the neck portion spanning a gap between the bolster and the heel panel at the posterior end of the sole structure; the heel clip being connected to the stanchion at the distal end of the neck portion, and being attached to the heel panel of the upper); and a heel counter disposed between the heel clip and the heel panel of the upper and being spaced apart from the sole structure at the posterior end. an upper extending from a first end in a forefoot region to a second end in a heel region and including heel side panels and a heel panel wrapping around a posterior end of the footwear and connecting the heel side panels; a sole structure attached to the upper and including a posterior end extending beyond the second end of the upper, the sole structure including a bladder having a first portion disposed between the second end of the upper and the posterior end of the sole structure, the sole structure including a footbed and a bolster extending from the footbed at the posterior end; and a support system connecting the sole structure to the upper, the support system including a buttress including a stanchion formed at a first end and a heel clip formed at a second end, the stanchion including a base portion attached to the bolster and a neck portion extending upwardly from the base portion to a distal end adjacent to the heel panel of the upper, the neck portion spanning a gap between the bolster and the heel panel at the posterior end of the sole structure; the heel clip being connected to the stanchion at the distal end of the neck portion, and being attached to the heel panel of the upper); and a heel counter disposed between the heel clip and the heel panel of the upper and being spaced apart from the sole structure at the posterior end. a buttress including a stanchion formed at a first end and a heel clip formed at a second end, the stanchion including a base portion attached to the bolster and a neck portion extending upwardly from the base portion to a distal end adjacent to the heel panel of the upper, the neck portion spanning a gap between the bolster and the heel panel at the posterior end of the sole structure; the heel clip being connected to the stanchion at the distal end of the neck portion, and being attached to the heel panel of the upper); and a heel counter disposed between the heel clip and the heel panel of the upper and being spaced apart from the sole structure at the posterior end.