Ainge is right that getting a star to agree to a trade is similar to a free agent pitch so you could say that the Garnett deal is reason to be optimistic. The main problem is not that the city or organization is undesirable now, rather that there are no other superstars on the roster. Not to ape frequent Rondo critic Jeff Goodman but I believe him when he says stars around the league are not clamoring to play with the guy. And while it's too early to make a call on Smart it's pretty evident Olynyk and Sullinger are not going to be star-caliber guys. Ainge can collect all the picks in the world but it won't make a difference if no star wants to come over.
Honestly I'm very pessimistic about the state of the Celtics right now because Love was the one star they had a shot at convincing to stay. No Love, no Rondo, gentlemen. They also lost the lottery AND the coin flip that would have made it possible to draft Exum. Now they have Smart who may be a good player but whose future conflicts with Rondo. They still don't have either a top scoring wing or defensive center, the two hardest positions to fill, instead stocking up on deep positions like PG and PF. The worst feeling is when you look at the roster and you can't even identify one player who could be the second-best player on a championship team.