Apprenticeship vs. championship: Inside Boston's plan to develop elite talent while chasing an NBA title

As the beneficiaries of a deal so lopsided that it probably should’ve been halted for “basketball reasons,” the Boston Celtics are in a unique position to field a team built to contend now while also preparing to compete long after LeBron James surrenders his stranglehold on the Eastern Conference.

That criminally favorable trade with Brooklyn, which set up Boston’s future with so many promising draft picks that it would’ve made the late Ted Stepien blush, has begun to bear the fruit of two top-three selections – Jaylen Brown and Jayson Tatum – with another likely on the way next year. Had they gone one spot ahead or below in the draft, Brown and Tatum would’ve been showered with praise and playing time and granted the leeway to flop or fly under patient, watchful eyes. They don’t have that luxury in Boston, where 17 banners hang as a reminder of the expectations for the organization and delegate unseasoned pros into extended apprenticeships. And, the offseason acquisition of $128 million man Gordon Hayward in free agency has pushed the Celtics closer to Cleveland, even as it came at the expense of trading Avery Bradley.

Celtics coach Brad Stevens has to find the balance between grooming Brown and Tatum for an eventual takeover while keeping All-Stars Hayward and Isaiah Thomas and veteran Al Horford in position to compete for something meaningful in the present. While Brown and Tatum are on different career timelines, Stevens believes what they offer now is in line with the Celtics’ current obligations to win. “Everybody equates development with playing time and I don’t necessarily equate that. And maybe it’s because of the situation we’re in,” Stevens told The Vertical. “But I can’t think of a better opportunity to develop than to have to add value to winning. If you can add value to winning at 19 and 20 years old, that’s a really good thing and when you’re held to that standard, then that is really difficult.”

What Boston is attempting to accomplish by incorporating high draft picks with a contending team isn’t unprecedented. Both the Los Angeles Lakers and Celtics took advantage of some trade wizardry in the 1980s to fuel their dominance of that decade. The Lakers went from a championship parade to drafting James Worthy No. 1 overall in 1982 and the Celtics were coming off a conference finals appearance when they added Kevin McHale with the third overall pick in 1980. And, if not for second overall pick Len Bias’ unfortunate death from a drug overdose just weeks after their 1986 championship, the Celtics would’ve been poised to extend their run well into the 1990s.

The difference in this endeavor for the Celtics is that their young players aren’t over 21 and don’t have three years of college experience. Brown and Tatum are both products of a one-and-done era that NBA commissioner Adam Silver would love to change. They will need time to develop before they can be expected to be more than ancillary contributors or high-end role players on a team with established stars that finished with the conference’s best record last season.

Brown, the rising second-year swingman, went through the challenging assignment last season, when he was held to a high standard and wasn’t afforded many opportunities to trip over his own feet. Stevens wasn’t afraid to toss Brown into adverse situations but let the rookie dictate what he could handle, which led to some difficult moments – such as Brown getting benched after struggling in the Celtics’ first-round series against Chicago. Brown, however, proved he could handle the demands of a coach who held him accountable when he used the experience to serve as a difference-maker in the next round against Washington.

Jaylen Brown showed some promise last season in a limited role with the Celtics. (Getty)

“You’ve got to adapt. You’ve got to grow up quickly. You’ve got to do what needs to be done. Got to mature very fast. In the NBA, there is no babysitters or none of that. So, you’ve got to come out, be ready to go and do your thing,” Brown told The Vertical. “It’s super hard, because you don’t have the chance to really grow and make mistakes. You’ve got to go out and kind of learn on the go. Got to go from a boy to a man quicker. You’ve got to do what needs to be done.”

Brown was able to earn more minutes last season because of his feistiness on the defensive end. His versatility in guarding multiple positions will be advantageous for Brown – especially if he can prove he can defend point guards – because Bradley is no longer around to form that fearsome perimeter defending threesome along with Marcus Smart and Jae Crowder. The Celtics won’t need to rely on Brown’s offense as much, with Thomas, Hayward and the already-skilled Tatum in the fold, but he is certainly capable of doing more on that end, if given the chance.

In Boston’s crowded wing rotation, Tatum has a polished and refined offensive game that will make it harder for Stevens to sit him as a rookie. Stevens’ offense relies on motion, screens and selflessness, but Tatum can break from those sets and produce in isolation – a skill that can beneficial in late-game situations. The Celtics needed more players capable of generating their own one-on-one offense to relieve Thomas. Tatum can hit tough, contested shots because of his high release and can use his deft footwork to create more space and scoring opportunities. He also knows that securing consistent minutes won’t be easy.

“It motivates you a lot,” Tatum told The Vertical about having to earn his keep. “Coming to the Celtics, I got to go in and find my role, whether it’s playing or whether it’s not playing. Everybody wants to play. I’m sure it will be mentally tough, at first, not playing. But winning cures all that.”

Stevens has never had to explain the situation to either Brown or Tatum because there shouldn’t be any ambiguity about how they should approach their roles on a deep team where veterans will also have to compete for opportunities. They have to be obsessed with quality over quantity. And, with the Celtics always in conversations to pry away the league’s top stars through trades, they also have to expedite their progression or risk being packaged for a more recognizable alternative. The situation undoubtedly played a role in Josh Jackson avoiding a workout with the Celtics and gleefully accepting a spot in Phoenix, where he is bound to lose a lot but won’t have to worry much about looking over his shoulder for minutes. Stevens doesn’t believe Brown and Tatum are being slighted in the least.

“It’s where you are,” Stevens told The Vertical. “It should be an exciting thing. Every one of these guys should be excited to compete for minutes and to earn things. All of our guys have to do that. And that’s a good thing.”

The last time a conference finalist was able to make a top-three pick, the Detroit Pistons made the now-infamous error of taking Darko Milicic with the second pick in 2003, ahead of Carmelo Anthony, Chris Bosh and Dwyane Wade. Milicic was 18 at the time, dealing with the culture shock of coming from Serbia, and never became much more than a disappointing tease as an NBA journeyman. Detroit was able to win a championship in spite of Milicic’s failures but only after the acquisition of Rasheed Wallace helped the franchise make the leap from good to great.

Brown and Tatum won’t fail as spectacularly. Brown survived his rookie season while sprinkling just enough potential around that there is hope for a promising career. His relative success came without having many teammates around to assist him with the adjustment by offering advice and encouragement. Having experienced the frustrations of having to scrap for every minute and the pressures of where you “almost have to be perfect,” Brown plans to tutor Tatum as the youngest player on the Celtics’ roster learns what works and what he can’t get away with.

Brown’s first bit of advice for Tatum: “Keep your confidence. You’re going to need it.”

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