What it comes down to is what your goals are as an organization.
If you believe your fan base is shallow enough to keep attendance up with amazing, exciting individual talent and marginal results, then you obtain players like Anthony or Iverson and extend them long term.
I doubt that Ainge believes that our fan base will tolerate anything other than contending for a championship or to be aggressively building towards one. Those should be the only goals that would satisfy a fan base for a team who has 17 championships.
The snitchster does not have the pedigree to excell in either of those scenarios.
Our fans have higher standards than that.