I'm OK with either option so long as the Cs wind up with the best players.
I don't think we can shoehorn this into a 2007 comparison or really any other. That team was led by an aging Paul Pierce and thus by the time a rookie was really ready to win it all (even Jordan took a number of years to learn how to really win in the NBA), Pierce would have been too far on the downside of his career to be that 1 or 1A star alongside said rookie. In '07 Pierce was 30 years old.
This team and this situation are entirely different.
1. There's no superstar on this team. IT barely made the All-Star team.
2. This team has far more viable trade chips than the 2006 team, especially when considering the salaries of the core players.
3. The core of this team is much younger. IT is 26. Bradley is 25. Crowder is 25. Smart is 21. Turner is the old man at 27. That's the top 5 guys in minutes played this year. That's not mentioning Olynyk (24), Sullinger (23) or the 3 rookies from last year.
4. Unlike prior years this team has cap space.
So what does this mean? In a nutshell, the Cs have both flexibility in talent and time. This team can pursue a win now strategy by signing FAs, trading for a superstar (or even more than one) and open a 6 to 7 year window for contention. Or they can sit back, draft the BPA, develop talent and continue to make deals to pursue a long-term strategy.
With all that said, I do think Ainge will commit to a strategy this offseason if he can. The timing is ripe to go one way or another. He isn't forced to choose a path but he is in the strongest position now to select one path or another. Waiting may keep both options open but then we he does strike it won't be from a position as powerful as the one he has today. At the same time, the options have to be open for him to choose - trading is a two way game and if there aren't other good options available I don't think he'll try to force a bad situation. Even if the worst case scenario develops - there are no good trading partners and the Cs drop to 5th in the lottery - I could easily see Danny selecting someone like Hield, pursuing some complimentary talent in FA and see how things shake out next year. After all, those Brooklyn picks are like the gifts that keep on giving.