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Why is company provided health insurance tax free, but individual health insurance is not?
This probably is a question that belongs on History but here's the basic reason: the or Employee Retirement Income Security Act (ERISA) of 1974 established that health benefits under approved plans were not taxable to the employee.  If the employer were to pay for an employees non ERISA approved individual plan, it would be a taxable benefit. The longer story is that many polticians (esp. President Richard Nixon) were concerned that public pressure was going to lead public sentiment toward nationalized health care.  This made health insurance more affordable to employees and effectively made it a cheaper way to compensate employees similar to how 401K contributions are worth more (in nominal terms) to the employee than an equivalent amount of cash.  While the law was not signed by Richard Nixon due to some other stuff that was going on, it was something proposed and pushed by his administration.