Hospital and medical expense policies were introduced during the first half of the 20th century. During the 1920s, individual hospitals began offering services to individuals on a pre-paid basis, eventually leading to the development of Blue Cross organizations.[65] The predecessors of today's Health Maintenance Organizations (HMOs) originated beginning in 1929, through the 1930s and on during World War II.[67][68]

The employer typically makes a substantial contribution towards the cost of coverage. Typically, employers pay about 85% of the insurance premium for their employees, and about 75% of the premium for their employees' dependents. The employee pays the remaining fraction of the premium, usually with pre-tax/tax-exempt earnings. These percentages have been stable since 1999.[58] Health benefits provided by employers are also tax-favored: Employee contributions can be made on a pre-tax basis if the employer offers the benefits through a section 125 cafeteria plan.
With the passing of the Affordable Care Act, or Obamacare, there is no longer a limit on how much your health insurance will pay.  Before Obamacare was law, health insurance policies had a lifetime maximum of $1 million, $2 million, or sometimes $5 million dollars. Someone with ongoing cancer surgeries and treatment could hit that $1 million mark easily, and then be left without health insurance unless they enrolled in an expensive, high risk insurance program. Today those barriers are gone, and individuals who need health insurance to treat chronic illnesses are able to get the care they need without worrying about hitting a maximum amount on their healthcare plan.
Prior to the ACA as of 2007, about 9% of Americans were covered under health insurance purchased directly,[53] with average out-of-pocket spending is higher in the individual market, with higher deductibles, co-payments and other cost-sharing provisions.[72][89][90] While self-employed individuals receive a tax deduction for their health insurance and can buy health insurance with additional tax benefits, most consumers in the individual market do not receive any tax benefit.[91]
As the population covered by Medicare grows, its costs are projected to rise from slightly over 3 percent of GDP to over 6 percent, contributing substantially to the federal budget deficit.[47] In 2011, Medicare was the primary payer for an estimated 15.3 million inpatient stays, representing 47.2 percent ($182.7 billion) of total aggregate inpatient hospital costs in the United States.[12] The Affordable Care Act took some steps to reduce Medicare spending, and various other proposals are circulating to reduce it further.
In the late 1990s federal legislation had been proposed to "create federally-recognized Association Health Plans which was then "referred to in some bills as 'Small Business Health Plans.'[79] The National Association of Insurance Commissioners (NAIC), which is the "standard-setting and regulatory of chief insurance regulators from all states, the District of Columbia and territories, cautioned against implementing AHPs citing "plan failures like we saw The Multiple Employer Welfare Arrangements (MEWAs) in the 1990s."[80] "[S]mall businesses in California such as dairy farmers, car dealers, and accountants created AHPs "to buy health insurance on the premise that a bigger pool of enrollees would get them a better deal."[81] A November 2017 article in the Los Angeles Times described how there were only 4 remaining AHPs in California. Many of the AHPs filed for bankruptcy, "sometimes in the wake of fraud." State legislators were forced to pass "sweeping changes in the 1990s" that almost made AHPs extinct.[81]
Disability income (DI) insurance pays benefits to individuals who become unable to work because of injury or illness. DI insurance replaces income lost while the policyholder is unable to work during a period of disability (in contrast to medical expense insurance, which pays for the cost of medical care).[123] For most working age adults, the risk of disability is greater than the risk of premature death, and the resulting reduction in lifetime earnings can be significant. Private disability insurance is sold on both a group and an individual basis. Policies may be designed to cover long-term disabilities (LTD coverage) or short-term disabilities (STD coverage).[124] Business owners can also purchase disability overhead insurance to cover the overhead expenses of their business while they are unable to work.[125]
Since 1974, New Zealand has had a system of universal no-fault health insurance for personal injuries through the Accident Compensation Corporation (ACC). The ACC scheme covers most of the costs of related to treatment of injuries acquired in New Zealand (including overseas visitors) regardless of how the injury occurred, and also covers lost income (at 80 percent of the employee's pre-injury income) and costs related to long-term rehabilitation, such as home and vehicle modifications for those seriously injured. Funding from the scheme comes from a combination of levies on employers' payroll (for work injuries), levies on an employee's taxable income (for non-work injuries to salary earners), levies on vehicle licensing fees and petrol (for motor vehicle accidents), and funds from the general taxation pool (for non-work injuries to children, senior citizens, unemployed people, overseas visitors, etc.)

In 1935 the decision was made by the Roosevelt Administration not to include a large-scale health insurance program as part of the new Social Security program. The problem was not an attack by any organized opposition, such as the opposition from the American Medical Association that derailed Truman's proposals in 1949. Instead, there was a lack of active popular, congressional, or interest group support. Roosevelt's strategy was to wait for a demand and a program to materialize, and then if he thought it popular enough to throw his support behind it. His Committee on Economic Security (CES) deliberately limited the health segment of Social Security to the expansion of medical care and facilities. It considered unemployment insurance to be the major priority. Roosevelt assured the medical community that medicine would be kept out of politics. Jaap Kooijman says he succeeded in "pacifying the opponents without discouraging the reformers." The right moment never came for him to reintroduce the topic.[23][24]
Fringe benefits are generally included in an employee’s gross income (there are some exceptions). The benefits are subject to income tax withholding and employment taxes. Fringe benefits include cars and flights on aircraft that the employer provides, free or discounted commercial flights, vacations, discounts on property or services, memberships in country clubs or other social clubs, and tickets to entertainment or sporting events.
Public insurance cover increased from 2000–2010 in part because of an aging population and an economic downturn in the latter part of the decade. Funding for Medicaid and CHIP expanded significantly under the 2010 health reform bill.[9] The proportion of individuals covered by Medicaid increased from 10.5% in 2000 to 14.5% in 2010 and 20% in 2015. The proportion covered by Medicare increased from 13.5% in 2000 to 15.9% in 2010, then decreased to 14% in 2015.[3][10]