Neeleman has started three airlines, all three successful. Morris Air merged with Southwest, and Neeleman did not fit in @ Southwest so he went north of the border (due to the 5-year no compete clause with Southwest) and help start WestJet. Along the way, he started up the Open Skies reservations system used by a large number of airlines. Once the 5 years of the no compete clause were, up then comes along JetBlue, and we all know how successful it has been to this point.
My pick is Robert Priddy, one of the founders of ASA and Valujet. ASA was one of the first airlines to emerge around the time of Deregulation (actually it started before Deregulation), and taking over routes abandoned by the majors as a result of Deregulation (prior to Deregulation, airlines like Delta were sending DC-9s and 727s into small cities like Columbus, GA
and once the CAB was dissolved, dropped the routes) made it grow at a fair clip. When Delta started up the Delta Connection program in 1984, ASA was one of the first airlines to be brought in. The rest is as they say is history. By the early 1990s, he had left ASA and when Eastern folded in 1991, he started plans for a new airline. Valujet was his baby. Unfortunately, VJ592 ended his major role in the airline, and like Lewis Jordan, he remains on the Board of Directors @ AirTran.