The role of metatarsus primus elevatus and first ray hypermobility is under scrutiny with regard to the pathoanatomy of hallux rigidus. Regardless of the underlying biomechanical cause, there is a subset of patients with hallux limitus present with concomitant insufficiency of the medial column identified on clinical exam and lateral imaging as dorsal divergence of the first compared with the second metatarsal. While cheilectomy and decompression metatarsal osteotomy are commonly used to mitigate retrograde forces at the first metatarsophalangeal joint (MPJ) level, traditional hallux limitus procedures do not address more proximal deformity of the medial column. Although the authors prefer to treat this complex condition with cheilectomy combined with tarsometatarsal joint arthrodesis, there is a paucity of literature on this approach. A prospective cohort study of consecutive patients was therefore performed to assess outcomes. Ten patients (3 males, 7 females) and 11 feet (8 right and 3 left) met the inclusion criteria. Mean follow-up was 21.9 months (range 12 to 52). Average age was 50.4 years (range 28 to 61). The average preoperative ACFAS score of 49.6 (range 29 to 61) improved to 78 (range 51 to 92) at 10 weeks postoperatively and 85.4 (range 60 to 100) at 1 year postoperatively. By 1 year postsurgery, 9 of 10 patients (90%) described their satisfaction level as very satisfied, and 1 (10%) was somewhat satisfied.