5. Challenge International Airlines


Maybe names do really matter, and calling an airline company a “challenge” hardly inspires confidence. But an overabundance of confidence may have led some aviation executives in the mid-1980s to create a passenger sibling to their all-cargo airline, using a fleet of 727s and 737s to fly from East Coast cities like Newark to Miami to points all over the Caribbean and Central America. Unfortunately, it never hit on a formula for success, and its moniker became a punch line when it ran out of money in late 1987 and declared bankruptcy.