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This article traces the growth of insurance in America and describes how its regulatory structure developed separately from the regulatory structure of other financial services. The authors describe how banks became involved in insurance activities as a way to expand their traditional banking services. Although regulatory restrictions at first impeded this effort, the Gramm-Leach-Bliley Act of 1999 has now opened the door more widely to the combination of banking and insurance. Nevertheless, banks will continue to face regulatory hurdles and restrictions under GLB that will impair their ability to compete in the insurance business. The article examines the landscape for bank insurance activities post-Gramm-Leach-Bliley and questions whether the "functional" regulation on which Gramm-Leach-Bliley is premised is an efficient or effective method to regulate financial products.