The Boston Celtics are currently in year four of their post-big-three rebuild. They have made a ton of personnel decisions in that time, and it’s hard to find fault with any of them. A lot of that is because the Celtics are not your typical rebuilding team. By now we are all aware of the fact that the team owns the rights to the Brooklyn Nets future, and they’ve used that advantage to remain competitive while waiting for those picks to arrive in full force.

In the meantime, they have traded for players other teams have looked over, such as Isaiah Thomas, Jae Crowder, and Jonas Jerebko. They’ve signed others to team friendly deals (Amir Johnson and Evan Turner), stockpiled a ton of draft picks. They even managed to re-sign Crowder, along with Avery Bradley, to some of the best bargain contracts in the NBA. After dolling out a max contract to Al Horford this offseason, the Celtics appeared to be on the brink of contention. Closer to being one superstar away than any team in recent memory.

Combine their abundance of talent with one of the brightest coaches in the business, Brad Stevens, and it would appear that the Celtics have played this rebuild as close to perfection as possible. Most middling teams hope to have one avenue to contention. The Celtics have all three.

But this raises an interesting question; can you be competitive and rebuild at the same time? It’s a hard question to answer because so few teams are ever in such a position. The Houston Rockets from earlier this decade may be the best example to point out. They never decided to tank, instead deciding to remain as competitive as possible and waiting for their chance to pounce. They eventually landed James Harden.

The Celtics, of course, are better now than the Rockets were in that time period (their 48-34 finish last season was better than anything the Rockets accomplished in that three-year stretch), and pundits will point to GM Danny Ainge’s pursuit of players as proof he is looking to follow the Houston model. And they wouldn’t be wrong. But they would be ignoring key contextual differences.

When the Oklahoma City Thunder traded Harden to the Rockets, they were doing so because they thought they were making the best financial decision. The assets they got in return (two first round picks, which turned into Steven Adams and Mitch McGary, along with Jeremy Lamb and Kevin Martin) were marginal at best, but the Thunder still had Kevin Durant, Russell Westbrook, and Serge Ibaka.

They were still contenders. Trading Harden did not represent a radical shift in philosophy. It was not an admittance of defeat by the front office.

Compare that to the situation in Sacramento. Outside of Cousins, the Kings effectively have nothing. No offense to Rudy Gay and Darren Collison, but if Cousins were to be traded, the team would go to the top of the lottery. If the Kings are going to part ways with Boogie, they are going to ask for a truckload of assets in return. Young players, veterans on good contracts, and high draft picks that might help sell the fans on a bright future.

In theory, the Celtics have all of that. So why has a trade not been done? Well, other than the fact that the Kings may not want to trade Cousins, it’s possible that teams may not be convinced that the Celtics young talents are anything special. They’ve been trying to keep their picks and trade them too. It hasn’t worked to this point.

Since 2013, when the Celtics parted ways with Paul Pierce and Kevin Garnett, they have drafted 13 players. Seven of them (Kelly Olynyk, Marcus Smart, James Young, Terry Rozier, Jordan Mickey, Demetrius Jackson, and Jaylen Brown) are currently on the team in some capacity and have played minutes this season.

Two others are overseas (Guerschon Yabusele and Ante Zizic), three are no longer part of the Celtics (Ben Bentil, R.J. Hunter, and Marcus Thornton), and one is tearing up the D-league (Abdel Nader).

A few of the players in that first category have become valuable contributors (Olynyk and Smart), while Rozier and Brown (a rookie) are working to get to that point.

For everyone else, it might be fair to say their careers have been stymied by a franchise caught between contending and rebuilding. Playing young players is not conducive to winning, but by not playing your young guys, you may be risking their careers stalling out. You also do not get to properly showcase them to other teams as potential trading chips. You wouldn’t buy a house before seeing it, and you wouldn’t trade for the 33rd overall selection in the draft before knowing if he could play first.

That is the Jordan Mickey conundrum. Mickey was signed to a four-year deal by the Celtics after an incredibly strong summer league showing prior to his rookie season. Since then, he has played in 25 games, and it would be unfair to say he has been good or bad either way. Barring injury, it’s unlikely that he sees much of an uptick in playing time as the year progresses. At best, year three of his career will begin without him ever seeing significant court time. Is this what’s best for the team, or for Mickey?

Amir Johnson is a solid veteran player. He understands positioning and help defense and has a good touch around the rim. But, he is not a rim protector nor is he a good rebounder. He also has a tendency to bobble passes out of bounds and his three-point jumper is an inconsistent last resort. For most teams, he would be valuable as a backup four, someone who can hold the fort for about a quarter per game.

For the Celtics, he has been a start the past two seasons, and while he has done a good job overall, it’s hard not to wonder how a player like Mickey might develop with more in-game reps.

Sure, there would be growing pains as he learns the nuances of NBA defense, wouldn’t that be the best way to get him on the path to becoming a better player?

Mickey has the tools to develop into a useful player for this version of the Celtics. He was a great shot blocker in college, and he has shown the ability to protect the rim in his limited minutes.

He hasn’t had the chance to showcase it yet, but he was also able to hit 35% of his threes in the D-league last season on a limited number of attempts.

R.J. Hunter is another example of the tight spot the Celtics find themselves. Rarely do you see teams part ways with a first round pick after one season, but that’s what the Celtics were forced to do with Hunter. Being the 28th pick, it’s unlikely that Hunter would ever succeed in the league in the first place, but it wasn’t out of the realm of possibility. Just one pick earlier, the Los Angeles Lakers selected Larry Nance Jr., who has become a quality contributor in year two for the club. 

Hunter had a reputation as a shooter coming out of college, but he hit only 30.7% of his threes in 36 games with the Celtics.

That’s hardly enough time to make a determination on a player, but the Celtics' bloated roster put them in a position where they had to choose between Hunter, and 2014 first round pick James Young. After a relatively even preseason battle, Hunter was cut.

Speaking of Young, the Celtics will soon have to make a decision on the former 17th overall pick. They did not exercise his team option for the 2017-2018 season, so if he doesn’t make an impression this year, you’ll be hard-pressed to find a scenario in which the team decides to keep him.

But, how can Young make an impression if he’s buried on the bench? Young has played in only 11 games this season, logging in only four minutes of court time since November 19. 

Young has often been a source of disappointment for Celtics fans, and in a previous season his playing time has been marked by missed defensive assignments, awkward attacks of the rim, and bricked triples.

Still, he remains only 21 years old, and no player has ever been a finished product at that age. Would he be better adjusted to the speed of the game with more opportunities? It’s impossible to say, but we may find out depending on his situation at the start of next season.

Marcus Smart, the team’s other first-round selection in 2014, was not subjected to the bench warmer treatment, but he may have been affected by team’s fast rise all the same. It would be ironic if true because Smart has been a big reason for the team’s relative success the past couple of seasons.

Smart is an impact player, a great defender, and when he’s on the court, the whole team seems to play with more energy. His middling stats don’t show just how much he means to the Celtics. But, he has been forced to play out of position during his first few seasons.

Originally drafted as the point guard of the future, Smart has spent limited time playing point guard. 

 

And this has caused Smart to play a game that forces him to go away from his strengths. Smart was a relentless driver in college, as well as a threat to post up smaller guards. He got to the free throw line and lived in the lane. In the pros, however, he’s become a three-point bomber, and his struggles from beyond the arc are well documented.

 

None of those positives he displayed in college have translated to his pro career so far.

Rather predictably, he has also struggled to run the show when asked, as all young point guards do. This season, Smart is averaging just 0.629 points per possession as a scorer out of the pick and roll and is turning the ball over on 22.9% of those plays. Last season, he scored 0.77 points per possession and turned the ball over a little more than 20% of the time.

Running an offense requires reps, and Smart is not getting them with the Celtics. When comparing his numbers with other point guards from the past two draft classes, Smart has run the fewest amount of pick and rolls by a wide margin.

 

What makes his lack of pick and roll reps even more confusing is that he may very well be the most natural point guard on the team. Most of his struggles in the pick and roll come from when he’s asked to create for himself, or when he fails to open up the passing lanes.

But when Smart operates as a playmaker, he has been very effective.

 

The numbers agree as well. Smart has been the ball handler in 173 pick-and-rolls this season when accounting for passes. The Celtics are scoring one point per possession overall on such plays. That number jumps to 1.252 points per possession when only including plays where Smart passes out of the pick and roll, which is in the 90th percentile, per Synergy. 

Letting a young player handle the ball more usually isn’t what’s best for a team trying to win, but if the Celtics increased Smart’s workload, it may not only pay dividends in the long run but this season as well.

The Celtics are in a precarious position, however, one nearly unprecedented in the history of the league. They have to balance winning with development, and try to find a happy medium within those two spectrums. Maybe letting their young players come along slowly will make them better in the future. Maybe their lack of game time won’t prevent another team from accepting them in a deal.

But, that doesn’t necessarily mean they can keep holding on to all of their cards. Soon, those team deals are going to expire. Their young talent will be up for extensions, and the Brooklyn picks will stop coming. If the Celtics themselves are unaware of everything their players might be able to bring, they won’t be able to give them the correct market value. It might not be long until they run out of those coveted assets.

Ainge knows the clock is ticking. He knows what the team needs if they hope to raise that 18th banner soon. And he knows the hefty price of acquiring a player that would allow them to realize that goal. If a superstar becomes available, he won’t hesitate to put together an offer. But, with a bunch of young players who aren't able to showcase their talents, he may have a hard time getting the other team to bite.