Yes, I'd be happy if Ainge went hard after Whiteside. I'd offer him a max deal despite his past.
Whiteside would complement our best defensive players (Smart, Bradley, Crowder), while providing shot blocking and rebounding.
Then hopefully Brooklyn--NETS us a top 5 pick. Simmons, Brown, Ingram would be good additions if we chose to draft a SF, while Labissiere & Bender would be ideal at PF.