My dissertation consists of three essays. The first paper explores the determinants of the share of workers' compensation benefits provided by self-insured employers over the period 1983-2000. We examine hypotheses that the self-insurers' share is determined by industry affiliation, price level, firm size, along with statewide levels of loss severity and frequency. Prior studies have produced mixed results concerning whether self-insurers are primarily high-risk or low-risk. Our panel regression analysis indicates that a positive and statistically reliable relationship exists between self-insurance and the health services sector which is characterized by high nonfatal incidence rates. Our findings put forth evidence that employers in the high-risk health industry are very likely to self-insure. The second article explores the determinants of self-insurance for workers' compensation liability by hospitals. Using cross-sectional hospital data in Pennsylvania, this study examines firm-specific characteristics of self-insurers. The logistic regressions suggest a link between the control type of a hospital and self-insurance. Nonprofit hospitals are more likely to self-insure, while for-profit hospitals prefer market insurance. Aside from large size, self-insured hospitals are associated with concentration of businesses within a state and the self-insurance pattern of their competitors. The prevalence of self-insurance among hospitals provides evidence that high-risk employers tend to choose alternative risk transfer. The decision to self-insure can be isolated from residual market arguments. The third investigates whether insurance activities (underwriting and agency) enhance the financial performance of financial holding companies (FHCs). Stiroh and Rumble (2006) and Yeager et al. (2007) have argued that extension of banking to non-banking activities provides no diversification benefits for FHCs eligible to consolidate banking and insurance services. Using quarterly panel observations of 510 FHCs over the period 2003-2005, we obtain two main results: First, when we employ the aggregate non-interest income as a measure of expansion, risk-adjusted return of FHCs is positively associated with a shift toward non-interest activities. Second, when we disaggregate the sample by FHC size, risk-adjusted return is positively associated with insurance agency activities in small-sized FHCs and positively associated with insurance underwriting activities in large-sized FHCs. An implication of our finding is that both small and large FHCs can reap diversification benefits as long as they choose the right niche.