The way to insure almost half of the United States' population is seemingly a tortuous process according to the past and present statistics. The ideological obstinacy of the private health care insurance sector and the comprehensive attempts of the United States' federal government to provide the widest range of health care and health care insurance advantages for their population gave birth to numerous socio-political distortions. Actually, the ones that seemed to be the less advantageous had always been the uninsured. They had outstandingly had less access to the health care insurance system, in general, and the financial system, in particular. Actually, almost half of the American citizens were currently uninsured and their illegibility to have access to the system had been weak. And, even though, numerous national and private health care programs came to reinforce the American welfare state, the rate of health care insurance enrollees could not stop declining. Now, the central question we target in this research paper is: why America was so weak to cover millions of uninsured Americans from 1990 to 2010? In this research work, we will try to investigate the history of health care insurance in the United States from 1990 to 2010, and even prior to that. We will state, as well, the reasons for such federal incapacity to legally insure their communities via plans, programs, and reforms. The work will also involve the ethical role that health care insurance should have played in reinforcing the system, and in raising America as the first nation worldwide to the rank it deserved to be in, if a national health care insurance system would have been adopted since settlement