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1. It would help to know the nature of the loan. Given the amount, I would suspect college loans or mortgage.
2. It would also help to know why, if he has the FRNs to pay the debt off, he doesn't just do it. After all, there is nothing suspicious about paying off a debt already listed under your own identity. The only guess I have from what you've shared is that much of his FRNs are already earned "off the grid" and paying off the debt would be a potential red flag. I'm not sure if that's an accurate assumption since if he has those FRNs in a bank, they are already being tracked and traced and that's as big a flag to the IRS and it is to anyone.
3. The most discrete way is for a third party to submit a money order to be applied toward the account in question. This can be done by your friend without involving third parties.
He can use FRNs with no real problem since the receiving party does not care what was used to buy the money order...they only care that the money order is good. Money orders (Western Union for example) are issued for less than a maximum amount with no questions asked at many retail locations. Since illegals use this "underground economy" like there's no tomorrow and neither the IRS nor Homeland Security/Gestapo lift a finger to investigate what goes on, the ONLY PROBLEM is doing too much business in one place or one time. Most places will let you do two maxed out money orders with no questions if you come in on rare occasion (big purchases are not unusual). If you did 4-5 maxed money orders every week, they'd probably get suspicious, but HERE'S THE GOOD NEWS...there are tons of these retail locations. You could get 10 maxed out money orders by just going around town and doing one at each location once a month.
3. The final issue deals with (a) where does his "money" come from and (b) what will the receiver think if a lump-sum payment shows up.
I'll answer the second question first. As a rule, all a creditor cares about is being paid. If someone dies and leaves you a ton of "money," you can pay off all debts real fast with no problems. However, in our Gestapo society, maybe it would still get reported as suspicious, and then the question comes down to, "Where did the 'money' come from?" If large payments are sent every month, this might stay under the radar. A lump sum would likely arouse suspicion.
Now, the first question might solve the second question. If one was to set up a "sham" charity, or some other legal 3rd party (LLC/Corporation) that has a charitable goal and have the proper "sham" papers drawn up (all legal but done just to create a needed paper trail should anyone ask questions), that "sham" entity could assume the debt, pay it off, and hopefully KO any inquiry at its mailbox. It would put a name and face to the source of the "money" paying off the debt and eliminate most any suspicion the recipient might have.
Hope that helps. It would really be useful to more understand where his concerns are rooted.
As I said, if he has the FRNs in a bank, the money is already being traced, and there is nothing suspicious about paying a debt already in his name with his own money. Lump-sum payoffs are totally legal and are not suspicious as many people have the money to pay off a debt but would rather have the bulk of their savings making money in the markets at a higher interest rate than the interest rate on the debt they are paying off.
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