In recent offseasons, the Boston Celtics have had to make relatively easy decisions regarding talented rookie-scale players eligible for extensions.

Two summers ago, Marcus Smart couldn’t agree on a new deal with the team – with a small amount of grumbling from Smart’s camp – only to ink a four-year contract with the Celtics a year later. Last summer, Terry Rozier – well aware of the situation in Boston and his place in it – seemed resigned to a season of uncertainty knowing his restricted free agency was insurance in the event Kyrie Irving left. (As it turned out, neither player will start at point guard for Boston next season.)

In both cases, the Celtics’ decision to wait and let the market set itself was easy. When Smart was a free agent, nobody needed a point guard. Rozier was never getting an extension before Boston knew what it needed at the point guard position.

This offseason, the calculus is a little different. The Celtics need to decide what to do about Jaylen Brown, and every avenue offers significant risk and potential reward.

Here’s a closer look at the options.

EXTEND HIM

In this scenario, remember two things:

Brown can credibly make the case that he is a winning player in the postseason and a potential go-to option.

Ben Simmons and Jamal Murray, who both have less on their playoff resumes than Brown, signed max extensions from their rookie deals this summer. Both Murray and Simmons have been top options on their teams (unlike Brown), but neither has been to the conference finals. Brown has been twice in three years.

In other words, Brown will likely be looking for a max deal or very close to it, and the Celtics would likely need to pony up to keep him.

Purely from a financial perspective, this would get complicated. The Celtics would need to feel very good about their roster as currently constructed – once they start handing out max extensions to their young stars, they won’t have cap space in any foreseeable offseason. Assuming Gordon Hayward opts in next summer, a max deal for Brown would likely put Boston over the luxury tax. The Celtics could probably negotiate a small amount of money off Brown’s contract to keep themselves under the tax if necessary, but Jayson Tatum’s rookie extension comes due the next offseason as well.

Brown has shown a rare level of adaptability that will serve him on essentially any team, which is valuable. Max-contract valuable? Danny Ainge will need to come to a decision on that front, and he may need to negotiate closely with Brown himself, who maintained in December that he doesn’t plan to hire an agent.

WAIT UNTIL NEXT OFFSEASON

The pros here are obvious: Brown will be a restricted free agent, meaning the Celtics can let the market set itself (and even depress it a bit by making it clear they will match any offer sheet). That kicks the can down the road and gives the Celtics a chance to evaluate Brown after what may be a less chaotic season.

But the cons are weighty as well. This offseason, the Celtics might be able to negotiate a lucrative but cap friendly deal to give Brown more security. If the Celtics let him get to restricted free agency, and if another team dangles the full max, Brown might be less charitable. Letting a player get to restricted free agency risks some damage to the relationship (although as Smart’s extension proved, a lucrative contract can smooth those edges). The Celtics won’t want to lose a high-value asset like Brown for nothing, but it remains to be seen if they view him as a max-value player.

Also worth noting: The 2020 free-agent class is drying up quickly. In a market with few available free agents (and especially at a position everyone in the league values highly), Brown would be a major prize. A team like the Atlanta Hawks could bite the Celtics preemptively by inking Brown to an offer sheet and forcing a tough decision.

TRADE HIM

Here’s one Celtics fans won’t like to consider. Three things:

Brown’s trade value is high, even after a difficult start to last season. He’s talented, playoff-hardened and extremely versatile, with plenty of room to grow at a high-value position. He can also reasonably point to last year’s dysfunction as a mitigating circumstance to his struggles, especially given his strong performance following his demotion to the bench.

One way or another, Brown would likely fetch a haul, although his rookie-scale deal would present some problems for salary matching. We won’t speculate here who exactly Boston could target, but starting center is an obvious area of need.

That leads into the next point: For all of his talent and versatility, Brown will be a little redundant on Boston’s current roster.

Tatum, Brown and Hayward have similar size and some of the same skills. Semi Ojeleye has likely earned a shot at some minutes at forward. Romeo Langford probably wasn’t picked 14th to spend the year in Maine. The Celtics will struggle to put together a traditional lineup next year, but it might be easier with Starting Center X in place of Brown in the starting lineup.

Celtics decision-makers, per sources, really like Langford (which feels obvious, since they used a lottery pick on him, but still warrants mention). Expecting Langford to be like Brown out of the gate is unfair: He’s a 19-year-old experiencing the NBA for the first time, while Brown has yet to be eliminated before the second round of the playoffs. But if the Celtics believe in Langford, his presence on the roster – especially given the logjam at wing and his distant rookie extension – could embolden the Celtics to make a move on Brown.

None of those options is easy. The Celtics could trade Brown, and he could turn into a perennial All-Star for whichever team acquires him. They could keep him and he could struggle, only to have another team proffer a max offer sheet next summer anyway. They could sign him and tie up their cap space, making Brown and Tatum the core for better or worse.

Boston’s choices are difficult: Try to negotiate a spendy (but slightly smaller) deal now, wait until next summer and risk losing an asset for nothing if they aren’t willing to max him, or make a move to acquire a player whose fit on the roster is a little more snug.

The clock is ticking.


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