TONI SAYS: Enrolling in Medicare over 65 with health issues

By Toni King

Hello Toni:

I am retiring on January 1,2025 and am beginning to search for the right Medicare option for me and my wife, who is having cancer treatment at a local cancer center. Her cancer treatment drugs are expensive, and I am concerned about the Medicare Part D out-of-pocket. I am a diabetic and use a flex pen and take high blood pressure medications. Most of my prescriptions are generic, except for the diabetic prescriptions.

Our Medicare Part B will begin January 1 as my company benefits will end December 31 of this year. What should I do to prepare for this medical insurance change? I will be 70 and my wife, Sandy, is turning 65 by the time I retire, and I want to be sure I do this correctly.

Toni, I’m looking forward to what you have to say about this stressful Medicare subject. Thanks, Scott from San Diego

Great question, Scott:

When we meet with clients during a Toni Says Medicare consultation, we emphasize that “Medicare is not cookie cutter … one size does not fit all!” Everyone’s finances, health, and prescriptions are different, and your health care needs, as well as the prescription drugs that you take, should be considered in finalizing your Medicare choices.

The cornerstone of Medicare planning at the Toni Says offices is discussing Medicare Part D prescription drug planning. Scott, it is imperative to search for the most cost-effective Medicare Part D prescription drug plan that covers all the prescriptions that you and Sandy have.

Many people simply don’t practice proper Medicare Part D planning. They are more concerned about their doctors and fail to notice whether their prescriptions are covered under their new Medicare Part D or Medicare Advantage prescription drug plan. (To understand Medicare Part D and the famous “donut hole,” read chapter 5 of Toni’s Medicare Survival Guide Advanced edition.)

Every Medicare Part D plan has a formulary, whether it is a stand-alone Part D plan or Medicare Advantage (Part C) with prescription drug plan. If your drugs are not on that formulary, you will pay 100% out of your pocket.

The 2025 Medicare Part D plans will be released this fall on October 1. Scott, I recommend that you and Sandy begin researching which Medicare Part D plan covers all your prescriptions and has the best price since you are retiring on January1.

Medicare Part B is like “gold” because of what it offers, and those receiving Medicare Part B for the first time need to understand the value of the Medigap/Medicare Supplement Open Enrollment Period. The Medicare & You Handbook discusses when to buy a Medicare Supplement: “The best time to buy a Medigap policy is during your Medigap Open Enrollment Period. This 6-month period begins the first month you have Medicare Part B (Medical Insurance), and you’re 65 or older.”

During this 6-month window you can enroll in any Medicare Supplement plan without having to answer any health questions and you cannot be denied coverage. After the 6-month window, then medical underwriting takes place, and those with existing health problems may not qualify for a Medicare Supplement Plan.

Many new Medicare beneficiaries explore the option of a Medicare Advantage plan (Part C) which can be a good option. With the health conditions that you and Sandy have, Scott, be sure that you discuss with all your doctors which Medicare Advantage HMO or PPO plans they accept.

Understanding the complexity of Medicare is exhausting to America. For answers to your Medicare questions, call the Toni Says Medicare team at 832-519-8664 or email [email protected]. Toni’s Medicare Moments articles have just been released at The Medicare Survival Guide Advanced edition is available at