It would've helped Boston's long-term outlook had they lost a few more games last season, landed Justise Winslow in the draft and avoided a pointless four-game smack from LeBron James and the Cleveland Cavaliers.
Instead they took the league by storm after the All-Star break, made the playoffs, then signed several productive veteran free agents over the summer. The organization's direction shifted, and it's not going back to where it was anytime soon, according to the Boston Herald:
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Boston can't win the title this season, but they can win a playoff series (or two), and are in position to swing for a dramatic mid-season upgrade should one present itself.
All those draft picks tied up in the performance of other teams allow the Celtics to play as well as they want without fear of needing their own pick to land high in the lottery. It's a brilliant strategy, even if things ultimately don't work out.
Getting high draft picks has been — and will remain — a part of the plan. But the Celtics no longer are relying on their own finish to secure such choices. They own Brooklyn’s first pick outright, and they will get Dallas’ next June if the Mavericks end up beyond the first seven after the final draft order is established. The Celts also can get Minnesota’s first-rounder if the T’wolves don’t end up with one of the top 12 lottery picks next year. The caveat here is that the Celts could still wind up making a high lottery run if one or more trades become available that would weaken them in the short term for greater gain down the line. But with the deal for David Lee and signing of Amir Johnson, it’s clear the club no longer is averse to moves that could win them an extra handful of games and still leave them shy of true title contendership.