Since the year of 2008, the American sub-prime crisis and the issue of financial derivatives dual problems caused the global finance crisis. At the same time, the Global Warming is getting worse which caused a series of natural disasters all over the world. The investment environment is seriously attacked by the storm of global financial crisis, and the international exchange rate is fluctuated largely, the re-insurance market is getting small, and the execution of deregulation in April of 2009 by Taiwan government making the premium income largely reduced. How to keep the premium income reaching at 100 billion NT dollars level, and how to react to bad economic environment are the major problems to Taiwan property insurance industry. Due to the economic crisis since 2008 until now, the huge variation of the exchange rate and the insurance rate of property insurance rate dropped drastically, which seriously affects Taiwan Insurance Industry, especially for automobile insurance of Property insurance industry. How to counter this big issue and find out the effective solution is the major purpose of this study. Selecting Top Five insurance companies as the study objectives to understand how they react to the deregulation policy and how they development after deregulation to find out the trend. Further to divide them into two groups- financial holdings and insurance company- to find out each group’s best model for deregulation.