The airline was established in 1969, as Wrangler Aviation and started operations in 1973, using Lockheed Constellation aircraft under FAA Part 91.

Between 1991 and 1992, issues of citizenship, ownership, and compliance with federal airline laws resulted in the conclusion and finding that through the unregulated use of "Delaware Company Law" and the practice of subsidiaries being parts of other subsidiaries," Wrangler Aviation did not meet the fitness requirements of a certificated airline of the United States.

[5] Further press releases on June 3, 2008, indicate that Tradewinds returned five Boeing 747-200F aircraft to the lessor and furloughed employees that operated the lines.

The company cited rising fuel costs and low demand, but plans to continue to operate flights during reorganization.

Tradewinds Airlines was renamed Sky Lease Cargo on September 4, 2011, and also changed its IATA and ICAO codes.