: Is health insurance a wash in this case? Let's say one makes 50k per year base at a company that pays 100% of the cost of a 10k per year medical plan. Now, a different company pays 0% for their similar 10k health care plan.

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It depends on whether you're paying for health care with taxable income. If you are making K but spend K on health care, you don't want to have to pay taxes on the K. Under current U.S. law, I believe, employer-provided health insurance is exempt from taxes, whether paid for by the employer or by the employee. So in that case it's a wash.

But if the second employer did not offer health insurance, and you spent K on a personal insurance plan, that K would be taxable income. You'd pay taxes on K but only net K after health insurance. In that case, the first employer is offering a better deal.

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Federal tax deduction on health insurance can be taken if you:

Itemize your deduction.
Costs over 7.5% of your income.

So, in your case, if you itemize your deductions, in the latter case you'd be able to deduct 5.5K of the health insurance costs.

In the former case however you "deduct" everything as you don't pay tax on the 10K at all.

So, basic math shows that with the K salary with K insurance paid entirely by the employer you'll end up with more net money in the end than with K salary with the K insurance paid by you.

In the first case you pay taxes on K, in the second case you pay taxes on .5K (with itemized deductions) or K (if you take the standard deduction), on the same K income.

Pub 502 for details.

Note, if you're paying for an employer provided plan directly from your salary, then you're paying pre-tax money in both cases, and then you'll pay taxes on K in both cases, so it is a wash. My calculations refer to the case where in the first case the employer provides the insurance, and in the second case you need to get your own insurance and pay for it separately, not through your pay-check.