Another possibility is your gifting of entire securities. Your brother tacks your basis and holding period, and you have no income tax consequences. This gifting should be unconditional, which means your loan payable should be outstanding right after the gift. Your brother may gift you unconditional cancellation of the loan. Those two gifts need to be reasonably apart in order to avoid any unnecessary IRS reclass of the gifts to the 1st scenario. Each you and your brother may file a gift tax return.