List year: 2006
Edge Petroleum was founded in 1983 as a crude oil and natural gas exploration, development and production company that was known for making high-risk investments. The strategy didn't carry Edge through the financial crisis.
Shortly after Edge made Fortune's list, its stock value started declining. The company planned to merge with Oklahoma City-based Chaparral Energy in 2008 to save it from extinction, but the deal fell through in 2008, with both companies citing the tough economic environment as reason for the deal's failure. Edge filed for Chapter 11 in 2009, announcing that all of the money from the sale of its assets would go to its creditors.