I honestly doubt itll happen.
The biggest contracts are in baseball and those are still under 300 mil. And I doubt baseball contracts will still be huge in 20 years when theres way less people watching.
Unless some new cba abolishes contract lengths itll be impossible in basketball.
The most likely would be in soccer, but all this assumes that the sports gravy train will just continue going up indefinitely and the tv bubble will never pop. And we know how likely that shyt is