Fail became Vice President of Commercial Mortgage Company in 1961 and President of Gulf South Mortgage and Investment Company in 1964. He founded Lifeshares Group, an insurance holding company, in 1970. From 1987 to 1997 he was owner and chairman of The Oklahoma Bank. In 1988, during the
savings and loan crisis, the
Federal Home Loan Bank Board approved the Southwest Plan, a program to provide government assistance to induce private capital investors to bail out failed
savings and loans in the
southwestern United States. While owner of CFSB Corporation, now known as Stone Capital, Inc., Fail acquired one such package of 15 insolvent thrifts, the Pard/Rose package. These were merged into a single thrift and renamed Bluebonnet. As a result of
regulatory changes in 1989, Fail has been pursuing a
Winstar suit against the federal government for an amount on the order of $100 million, which was still running as of 2006. In order to buy Bluebonnet, in September 1988, Fail borrowed $34 million from Mutual Security Life Insurance Co., a
Fort Wayne, Indiana company he had bought the previous year while it was struggling with debt. Mutual Security became insolvent in August 1990 and moved its headquarters to
Lincoln, Nebraska and
Dallas, Texas; its Indiana business was seized by state regulators, prompting
BusinessWeek to describe 130,000 policyholders as "in limbo". Also in 1990, another of Fail's insurance companies, Farm and Home Life Insurance, failed and was placed in receivership by the Arizona Department of Insurance. In March 1992, Arizona sued Fail and his deputies for civil racketeering fraud in an amount in excess of the company's $101 million insolvency, alleging that "Mr. Fail and others were engaged in an elaborate scheme to drain millions of dollars out of the company...", resulting in its failure. The case was settled for $78.8 million. The
Senate Judiciary Subcommittee on Antitrust, Competition Policy and Consumer Rights investigated the Bluebonnet deal in 1990 to determine, among other questions, why Fail's bid succeeded despite the 1976 fraud conviction of his company, which should have been a "presumptive disqualifier" per FHLBB regulations. Initially, most of the criticism came from chairman
Howard Metzenbaum, who described the deal as "an abomination, the worst case we have found" among the savings and loan bailouts. When Fail admitted to incorrect disclosures of his legal history, Senators
Arlen Specter and
Orrin Hatch also voiced their concerns. ==Philanthropy and community involvement==