It looks like he is out of luck. You are correct on the alimony after 2018 plus there was no alimony stipulation in the divorce agreement. He should have waited for the QDRO to be set up. It should not have taken 9 months. Since the ex-spouse did not receive the payments from a qualified plan, they would not be considered QDRO benefits. Here is a Tax Court case that addresses this situation:
According to an addendum to their divorce decree, the taxpayer deposited pension distributions into a joint account with his ex-wife for her exclusive benefit. He did not report the pension distributions on his income tax return. The Tax Court held the addendum failed to be a QDRO because direct payment was not made to the ex-wife as an alternate payee. Distributions were taxable income for the taxpayer even though his ex-wife actually received the money. (Hackenberg, T.C. Summary 2010-135)IRAs.
