When I retired from a municipal fire department I was able to buy my unused sick time, vacation time, and compensation time to purchase paid-up health insurance under the City Blue Cross/Blue Shield Plan. I was able to purchase $70,000 of pre-paid paid up insurance wich was paid directly to the City and they pay the monthly premiums until the $70,000 is exhausted. They predict that to be approximately 10 years. The problem is the total $70,000 is added to my total income for the year which puts me in a much higher tax bracket. My question is, since I have paid the total amount for the pre-paid insurance this year, can I deduct the total amount this year as a medical expense or does it have to be amortized?