With expansion and the new media deal we will see 10% raises to the salary cap each year. My rough calculations say that someone signing a supermax in 2028-29 offseason will have a 5th year that could hit 100 million, so the year 32-33. That timeline could speed up too if the nba players vote to allow the salary cap to jump more than 10% a year.

NFL might happen first as they don’t have the same max salary restrictions.