Ainge saw it happen with the Celtics of the early 1990s. And now, as the president of the Celtics, Ainge is at a crossroads. Does he blow things up and trade away any or all of the Big Three in Paul Pierce, Ray Allen and/or Kevin Garnett? Or does he keep them together and risk having the chance to rebuild with pieces brought in a potential trade?
It's the latest decision for Ainge in what's been an interesting time as a Celtics executive. He oversaw Celtics teams that were just miserable in the earlier parts of last decade. They then got a little better before getting much, much worse.
Then, in his crowning moment as the organization's top basketball decision-maker, Ainge's shrewd moves helped land Allen and Garnett in Boston and ultimately, delivered the Celtics their 17th NBA title.
It's been an up-and-down tenure for Ainge in Boston, one that may ultimately be defined by what he does with the Green in this time of uncertainty.