...
I am "coaching" a former ham. His license expired well over 2 years ago and
he was a pre-1987 Technician. I told him he needs to re-enter the hobby
fresh, as if he'd never been there.

Was I right?

No.

He does have to take element 2, but upon presentation of his pre-87 expired
technician license, that element 2 test will give him a GENERAL class license,
not technician (as it would for someone who was starting "fresh").