1. SS from dear departed ex-wife.
Step one - Review the ss.gov website - lots of questions answered there. I bet he is eligible, he is past 60 and was married over ten years.
Step two - Call SS with a list of questions, get clarity.
Step three - At the end of the SS call - make an appointment at your local office or find out if during covid they have other options - chats/telecon.
Review the list of documents required by the SS to start your claim - it's right there on their website.
It is not a problem - all you need to do is ask! I'm a widow and his financial situation aside - this is no different from any other inquiry about eligibility for SS. You call - they answer and if you forget to clarify something you call back.
I'm sure he isn't the only person in the US who ended up living on the fringe because at some point it all became overwhelming.
Not all of them are alcoholics or dead beats.
He may well see his first SS check within three weeks of putting in his application. DO IT!
If he is computer savvy, set him up with an online account. If not, choose a bank within walking/driving distance with enough branches in the area where his SS direct deposit will go.
Set up his phone with a text alert so he knows each month when his deposit has arrived.
That's all normal stuff for us, but he may have forgotten and a lot has changed in the banking industry in the past ten/twenty years.
Either way, even if he banks with brick and mortar show him how to set up the account and navigate online - he'll figure it out.
Hopefully he has a DL that he can use as ID, if not, he will have to renew or get a state ID.
He'll need to know his SS and his wife's SS before he calls.
He will need help and positive encouragement in dealing with all this - it will be scary and hopeless to him, but in reality it is just paperwork.
He can do this with a bit of guidance which will lift his spirits and help him tackle the next step.
2. Once you've established eligibility and applied for SS - determine if the IRS will actually take away all of his SS. Unlikely, but this can be clarified easily enough via a search on their website or a direct phone call.
Clarify what if any percentage the IRS will take...maybe he can survive with receiving only part of the SS for a while.
That would be good news and give him something to look forward to - eventually the entire SS will be his and the IRS demands satisfied.
Impress upon him that from now on - he will do a tax return each year.
He'll be below the poverty line and get money back in the future
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3. I have no input on the covid or unemployment, but I'd look into it per the posted suggestions.
Elderly help. My experiences in that regard showed me how screwed you are if you are old and have no way to support yourself.
Regardless - since he is already 64 - it is important that he applies for Medicare about four months before he turns 65.
I was one of the dummies who never realized that everyone is automatically eligible for Medicare at age 65 but you have to pay a penalty for life if you do not apply within three? months of turning 65.
Nobody ever told me that...
Given that he has no income to very little income - perhaps he is eligible for Medicaid and expanded Medicaid? even now?
4. Child support - find out the particular laws that govern this in your state. If it is true that the money is owed to his ex-wife's estate - he needs to deal with it!
Where there is a will there is a way - this is one area where I would seek legal help.
Just rambling here - but if his kids are the heirs of the estate - perhaps he could make payments to them which would then be returned to him by his kids in view of his having paid college expenses?
The goal is to keep him from becoming homeless, destitute and depressed.
I'm sure everything will be even harder if he has no permanent residence.
A place to live and certainly an application for food stamps is the very first order of business. I imagine he went to a church or food bank at this point?
Perhaps he can manage to continue to rent a room from his friend once he knows how much he will receive from SS.
From what the OP said this man has always worked - so I see no reason why he couldn't work a few more years and sort this out.
Some of it will be more difficult and take longer but the SS and IRS are both relatively easy to tackle once you have a plan.
Good Luck - it isn't up to us to sit in judgement. Like you said OP there are definitely good people out there who just don't have the wherewithal to deal with and operate successful in our modern society.
The older you get the harder it is to fix your life, but it isn't impossible.