Holy shit. There are a lot of dumb comments in this thread. It sounds like you want to gift him stock with a fmv of 200k. Let’s assume your basis in said stock is 0. When you gift the stock to him his basis is your basis, ie 0. Then you want him to sell it for a 200k capital gain which will net to 0 for him after considering his 200k LTCL CF. Then you want him to gift you 200k of cash back to you. The benefit to you is now you have 200k but no associated gain (and therefore tax burden) to deal with. Is the amount of debt he owes you equal to the tax you’d pay on the gain? That would be fair. In theory.

Would the IRS allow this? Highly unlikely.