Is it time for the Boston Celtics to drop the rebuilding attitude?

The last nine months went as well as one could hope for the Celtics. They won 53 games, made it to the Eastern Conference Finals, won the lottery, and signed another max player. The team not only got a talent upgrade, but it replaced some of the more finesse and lovable players with tough, big, and versatile veterans who will give the Celtics the added edge that they seemed to lack at times last season.

One question that still looms over the Celtics is: What exactly are they? Is this a team ready to win now, or is this a team still building with an eye towards 2022? Being able to have your cake and eat it too is what makes the Celtics’ building model so awesome in terms of content, but it is also frustrating for those who want to know how to evaluate this team. Last year, the Celtics lost in embarrassing fashion to the Cavaliers, but most fans already had their eyes towards the offseason. When the team wasn’t able to get Paul George, it wasn’t viewed as a failure because Boston has the assets that allow them to be patient. There always seems to be a fair but slippery scale on which the Celtics balance. But regardless of how you flip it, this is finally the first real crossroads the Celtics will face in their three-year project of being the best rebuilding team in the league.

I asked a simple question to the fanbase today:

The answers I got were varied, but also telling. Some said we need a big who could protect the paint and grab rebounds, others said we needed another elite shooting wing, and others said we needed another stretch 4 who could also create. All of these suggestions painted a clear picture—we all believe the Celtics need another piece to catch up with CLE, but what if that piece is still 5 years away from his prime?

Jayson Tatum projects to be a big-time scorer who will work best as a small-ball 4 one day. Jaylen Brown is a hard-nosed defender who could become one of the top two-way players in the league one day. Ante Zizic has potential to provide the Celtics with a post presence who could protect the paint, grab rebounds, and get out in transition... one day. The theme is interesting, but it could lead to potential issues for the Celtics in the next coming months. Here’s an example.

Let’s fast forward to February: The Celtics are as good as advertised with a 34-10 record heading into the All-Star break. During that stretch they had a convincing win against the Cavaliers and played a healthy Warriors team extremely tough in a January classic. Meanwhile, some of the anointed Western Conference powerhouses are struggling to keep their heads above water, and two of them think it might be time to get ahead of the curve. The Pelicans call first, offering the Celtics DeMarcus Cousins in hopes that maybe some added wing depth to put around Anthony Davis is the best way to unlock his true potential. Then, you get a call from Oklahoma: Paul George is not happy with his role in the Thunder and has given the team confirmation that he’ll be leaving at the conclusion of the season. Presti is looking for at least the Lakers pick even if it means giving you his own and some future assets down the road.

There’s no more Tyler Zeller or Amir Johnson to trade anymore. If those calls come mid-season, the Celtics will have to match salaries and will be forced to part ways with veteran members of the core, key members of the farm system, picks, or a combination of all of them. Put more directly, if this Celtics team wants to take that last step to true contention with the Cavaliers and Warriors, then they’ll have to seriously become a win-now team and pay the assets that it costs to become one. Either that, or be comfortable sitting back and being a tier below in hopes that the players that you’re picking may one day bring you to.... this point? People at all levels understand that the draft is crapshoot, and even with the allure of picks, to choose the win-later team would be to assume that the players you’ll find will have talent superior to Isaiah Thomas, Gordon Hayward, Al Horford, and that they’ll all develop and stay with the team during their primes. That’s a big gamble.

If the price of putting together a title team is some combination of Marcus Smart, the BKN pick, LAL pick, MEM pick, and a guy like Jae Crowder, is keeping those pieces in hopes of winning later a safer gamble than getting a proven player who will most likely take your team to a new level?

The Utah Jazz did everything right as a franchise. (Forget the revisionist history of not signing Hayward to a 5-year max, most agreed that it was the right move at the time despite the risks.) They have an all-NBA center, one of the most electric passing point guards, some of the best wing depth in the league, and Hayward still left simply because his college coach was coaching a team just as good in a much easier conference. Three years from now, the new monsters of the NBA could be the Bucks or Sixers, maybe even the Lakers, nobody knows. What we do know, however, is that the Celtics are the second-best team in the conference with the pieces to make themselves the best team in it and possibly the league. Is a chance at going for a ring now any more dicey then hoping teenagers project to be superstars?

The Celtics may be forced to answer that question sooner rather than later.