I would ask a trusted friend, or his stock broker, to act as a third party go-between – at no charge, of course. Either one would be happy to do it.

An attorney is the solution. And I would consult whichever lawyer or firm handled the windfall enabling the current necessity. I am sure they would fulfill your request for a surprisingly reasonable fee. It’s such a painless and simple task compared to the customary snake fights comprising the lawyer’s usual fare.

It’s the anonymous part that is the difficulty since the loans and mortgage would have to be paid by the payee, I would assume. So I would think the donation would need to come to them directly. But perhaps a financial or estate planner would have a better idea.

Kudos to the benefactor!

It can be done. But it is a tricky business. If you think about it, there are surely individuals in the financial offices of all mainline schools well versed in such exercises. And as TW notes above the trick (in my view) is to pay down the debt anonymously while minimizing (or eliminating) the tax bite. For instance, that $15,000 limit that TW mentions above means you can in effect

The anonymity is the key here, not fees or taxes, couple of good places to start. Thanks guys.

What a generous person!
I’ve thought about doing something like this if I ever won the lottery. In my head I planned on having a general conversation with my friends about their mortgage. What percentage are you paying? Really? Not bad! Through which institution?
I assumed I could then go to that institution and say that I wanted to pay off the mortgage for my friend anonymously. I can’t imagine they would decline my money, but it went really smoothly in my head.

You already have some good answers here. To pay off the mortgage he will need to know the current note holder and the account number, which you can usually find in county records or pay a title agent to research the mortgage holder.

As far as the student loan I have no idea how to find out what entity owns that note? Is it the government?

If your friend is not worried about incurring a gift tax, I would say pay a little more and let a lawyer handle it. Maybe an estate lawyer can easily research both and do the pay-offs? That is just a guess on my part. Possibly, the money can go through the lawyer’s account so there is no trace of the gift givers name.

If he does it on his own I think he could pay with a money order or cashier’s check rather than a money transfer, although for some reason it would make me uneasy sending one of those through the mail.

This reminded me of an old Tv series called “The Millionaire” ( series 1950–1960).
Here is the link to that TV sorry and what the results of giving some people were and not always a good thing.

Here it explains how he approached the people to hand over a certified check.
Although one could hire a person to deliver to recipients just like a lawyer hires someone to serve a summons to appear in Court anonymously.

https://en.wikipedia.org/wiki/The_Millionaire_(TV_series)

In the movies, it’s always either a solicitor or a banker. In any case, an authorized agent who conceals the donor’s identity. The plot of Great Expectations hangs on that.

These days privacy and identity are much more heavily guarded (ironically because they’re more readily compromised). I’m wondering if a straight certified check or other instrument issued by a bank and sent by mail would be the simplest and most direct.