While coarctation of the aorta may be a simple obstruction to flow from ascending to descending aorta, its repair has been varied and complex. Historically, many of the surgical options tried for this lesion have met with initial enthusiasm until long-term data on recurrence rate and complications were accrued. This review will present the complexity of historical therapeutic options with particular focus on long-term outcomes. Before any surgical or transcatheter technique for coarctation therapy can be considered a standard, awareness of the twenty-year outcome is warranted.