The Pegasus “Wings” Program (Wings) is an innovative 501(c)3 non-profit ‘pilot training’ scholarship fund initially targeting deprived youth in the Greater Hartford community. Wings was authored and developed under the auspices of Pegasus Air Charter – a progressive Air Charter company headquartered at Brainard Airport, in Hartford Connecticut. Pegasus also offers Air Ambulance services, Professional Flight Training services and Unmanned Aerial Vehicle (UAV) aka Drone services. The explicit mandate of the Wings program is Workforce Development – an effort organized in partnership with the City of Hartford – specific to the development and implementation of a radical and turnkey pilot training pipeline. The timing of Wings; its development and execution, as a sustainable jobs-producing program, is also germane given the current industry condition and forecasts relating to the chronic shortage of commercial pilots both at home and abroad. The Pegasus “Wings” Program was developed on the basis of true-life data relating to the global shortage of commercial pilots. This has inspired the development of Wings’, further solidifying its mission of seeking-out, engaging and training deprived teenagers to become Commercial Pilots. Once successfully trained and certified, Wings graduates will receive guaranteed job placements within Pegasus’ air charter operation – as First Officers, ultimately placing them on a progressive career track towards becoming successful airline pilots.