This study examines the impact of financial constraints on firms' risk taking decisions. By using data from insurers of the NAIC (National Association of Insurance Commissioners) over the 2006-2013 period, this study finds that insurers with a better rating, as well as higher dividend payouts, are significantly and negatively related to risk taking decisions, which is consistent with the primary rationale of the CEO hubris argument, the risk sensitivity theory, and the prospect theory. The evidence proposes that regulators have to pay more attention on firms with higher financial constraints who intend to take more risks.