Health Insurance Inside of Union Assessments

If they specifically break out part of the payment as health insurance, go for it.  But if a small part of union dues includes health insurance, you can't just claim the the full amount of dues as health insurance.

Back when unions had some strength, employers would pay them for the health insurance coverage of employees.  (This was invented back in the 50s as a tax loophole, since those premiums were not taxable and wages were subject to higher brackets than they are now.  The consequence was the only major country without national health insurance.)  Now, there may be some unions that don't collect enough from employers, so they have to collect from members.  But presumably some other benefits are included in those dues, so it would be like deducting my HOA assessments just because part of them pays the health insurance of the property manager. 

I used to have a client who insisted that it was necessary to pay the dues assessment for retirees -- something like $250 a year -- in order to continue coverage of the union health insurance plan, which at that point must have been a Medicare supplement.  He claimed it as a medical expense, and I went along with it, since he didn't exceed the 7.5% floor anyway.