This dissertation investigates the pricing and the market reaction to the announcement of private placements. A sample of 181 private placement announcements during January 2002 and March 2007 in Taiwan was obtained. This dissertation consists of two essays on the private placements. The first essay identifies the conditions determining insiders will pay more (or less) in private placement. We explore the argument of private placement pricing sold to insiders by considering the changes in the control power of the largest shareholders in private placement, using the Banzhaf power index to better reflect the largest shareholder¡¦s relative power of influence. Our results indicate that, if the existing insiders maintain their leading control status, in cases where insiders are the main investors, private placements are issued at deep discounts that benefit themselves; however, in cases where outsiders/new insiders are the main investors, outsiders and new insiders will pay relatively more when existing insiders dominate. Contrarily, if existing insiders fail to retain their leading position and become less powerful after private placement, outsiders and new insiders buy at lower prices. In more than 65% of the sample, the largest shareholders lost their leading control status, and the issuer¡¦s ownership structure becomes more concentrated following private placements. In the second essay, we examine whether the announcement of private placement and public offering share the same announcement effects. In particular, we investigate whether the market reactions to private placement announcements vary with different placement motivations and investor types. In addition, we focus on the dark side of private placement by studying how the stock price reaction to private offerings when insiders intentionally lower the offer price to self-dealing, or when within-group private placements are motivated by the controlling shareholders¡¦ tunneling. The results indicate that private placements generally result in a positive wealth effects, however, public offerings associated with negative announcement effects. The market reacts more favorably to private placements in which a strategic alliance or merger are involved, or to private placements where investors actively participate in the management or even procures the controlling rights of the company. It suggests that the motivation and investor type of private placement convey important information to market investors regarding the issuing firm¡¦s performance. Moreover, we have evidence to support the dark side of private placements. For issuing firms with stronger tendency towards self-dealings by insiders or tunneling in transactions between firms within a business group, they are more likely to have poor performance after private placement. However, we have no evidences to support the firm quality hypothesis.