<prompt> Human: So my Mom is 63, divorced and has never worked. Instead she took care of their parents my grandparents until they died and inherited a 1M in stocks, mostly Kraft and Phillip Morris. A few years ago she has some crippling health problems and at the same time she discovered her long time financial advisor had been stealing five figures worth of money from her. After she got better she was relieved to be done with everything she settled out of court for less than he took. Now she is terrifying of financial advisors. The biggest problem is that the stocks she has in Phillip Morris have a 0 cash basis. And before everyone jumps in and says we can research this and get the actual basis it has been decades, and multitudes of people of who have attempted to find the cash basis and nothing. Its 0. PM makes up the bulk of her stocks but Im not sure exactly how much. She never worked outside of being a caretaker so she has no social security or any type of retirement account. She is, as we understand, eligible for her ex spouse who has died. She will be 65 next year. She is selling her house in PA and expects to receive 80-100k in net proceeds which she is going to use to build an addition or finish our basement to the property I own in Maine. Basically Im of the uneducated opinion that she needs to diversify her portfolio into something much safer than the individual company stocks of 4 or 5 different companies. The problem is the capital tax gains are crippling. She has no debt other than a 200 car payment but her health insurance is 1500mo as she has been ineligible for assistance because of her stock holdings. How can she protect what nest egg she has left? Does taking her exs social security now impact her drawing? Will she be Medicaid eligible with her stock holdings? I want to help her make sure she has enough money for the next 35 years as her family is extremely long lived. My spouse and I do well but we are behind on our retirement without worrying about supporting hers. Thanks in advance!Edit: Regarding the cost basis - When my Grandmother died the stocks had already been in my moms name for years beneath a family trust. None of us were able to get a step up because she was still alive when we got our stocks. No one received stocks or money upon her death.Edit: Thank you to everyone that commented! All this info has been super helpful. Im going to get to work on explaining the differences between FP and CFP and what some of the possible options we can explore with an actual CFP. I hope to get her set up with a good pro ASAP.  <response>: I cant speak to the stocks and others seem to be covering that, but as far as your healthcare questions go:MediCARE is federal health insurance for all seniors. She will be eligible as soon as she turns 65 and it is not means tested. Its pretty decent basic insurance, probably better than what she has now.MediCAID is federal health insurance for poor people of all ages. There are some things that Medicaid covers and Medicare does not, the most notable one is long-term nursing home care. Essentially, this is not covered while you still have assets and are only on Medicare, but if you spend your money and become poor enough to qualify for Medicaid, then it gets covered. But it sounds like your mom is pretty healthy at the moment, so shell be just fine with Medicare for a while. 