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Do I have to work till I'm 65 to get Medicare through the school system for TRS retirement. Then I still won't get social security what do I do for the expense of insurance/

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Go to the UFT website and find out when the next pension clinic for your tier is. Or just call the UFT. They are pretty good at explaining retirement benefits.
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Talk to your union steward about your plan, he/she can probably find a retirement seminar for you to attend. You are still too young for social security and Medicare does not kick in until 65. Medicare is not through the school system, it is a federal program.
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