Sky King also conducted flights of deportees to undisclosed destinations on behalf of U.S. Immigration and Customs Enforcement (ICE).

The airline filed for Chapter 11 bankruptcy protection on March 9, 2010, after it was unable to meet the payment demands of one of its largest creditors, fuel supplier Mercury Air Group.

A series of events in 2005, including the NHL lockout, the devastation of Hurricane Katrina, and the spike in jet fuel prices required Sky King to find an alternate way of running its business.

By moving to Lakeland, Sky King was able to reduce its maintenance costs (by eliminating cross-country ferry flights) and focus on expanding the East Coast markets it served.

In October 2010, Sky King was purchased by Aviation Capital Partners Group and shifted its focus away from private charters and towards providing scheduled services.

At the same time, Sky King again filed for Chapter 11 bankruptcy protection and laid off over 20 pilots, 30 flight attendants, and others in operations, maintenance, and the Lakeland office.

[9] On November 30, 2017, USGlobal Airways issued a press release stating that their agreement to purchase Songbird had been terminated as it was not the "best decision for the company".

[citation needed] Sky King provided charter aircraft to numerous touring agencies with flights into Cuba.