Although functional and clinical outcomes after total ankle arthroplasty have been promising, a steep learning curve has been recognized. In addition, the performance of concomitant hindfoot realignment procedures is controversial. The purpose of this study was to report on a single surgeon's experience with the first 50 total ankle arthroplasty procedures. We wanted to define the characteristics of the learning curve and whether the rate of complications was increased in patients who required complex reconstruction for preexistent foot and ankle deformities. This was a retrospective study of 50 cases with an average follow-up of 24.2 months. The patient population consisted of 18 men and 30 women with an average age of 57.6 years. Twenty-six percent of the cases had concomitant bony realignment procedures, while 20% had prior history of major hindfoot corrective procedures. There were 19 cases with intraoperative malleolar fractures, 12 cases that exhibited some degree of malalignment, and 6 cases of syndesmotic nonunion, and 8 ankles required early component revision. Minor wound complications that resolved with local wound care occurred in 9 cases, while 1 patient had a major wound complication requiring flap coverage. Each of these complications, other than wound complications, decreased with the surgeon's experience. Our results also indicate that the performance of major realignment procedures at the same time of implant arthroplasty is not associated with an increased incidence of complications. The results of this study suggest that total ankle arthroplasty is associated with a learning curve. Perioperative complications may potentially decrease with surgeon experience.