While most NBA offseason business gets resolved in July, rookie contract extension talks often drag out all the way to the deadline of the day before the regular season starts. That applies to the Celtics and Jaylen Brown who have until 6:00 PM on October 21 to potentially come to terms on a deal that will keep Brown in green beyond the 2019-20 season.

Danny Ainge and the Celtics haven’t agreed to an extension of a rookie scale deal since Rajon Rondo was eligible back in 2009. They also have a history of leaving these negotiations late into the offseason (see: Smart, Marcus) so it’s no surprise that Boston Sports Journal reported that Brown and the team had not had any discussions yet at the beginning of July.

With about a month remaining on the clock it’s worth looking at the landscape the negotiations are happening in and then at some player comps to try to determine what a fair offer could look like.

Extension Rules

Jaylen is eligible to sign up to a five year contract that would start in 2020. However, if it is a five year contract it must be for his full max salary, which is projected to have a first season salary of $29 million ($29M) and total $169M. If he signs for four years or less the deal could still start as high as $29M in the first season with maximum raises of $2.32M per year. A four season max would total $129.9M.

If they don’t reach an agreement then Jaylen will become a restricted free agent next summer. His qualifying offer, which is a one year deal that the team is obligated to offer if they want to make him restricted, would be for $8.6M. His cap hold, the amount that his rights cost against the salary cap, would be for $19.6M.

If he were to go into restricted free agency and sign an offer sheet with a competitor, the starting max salary would stay the same but with smaller raises; the max four year total would be for $124.7M.

If he were to sign a five year extension then the Celtics would be limited to holding a maximum of one more player on a five year rookie extension while Brown is on that contract and the Celtics roster. If you’re wondering why having Kyrie Irving made it illegal for Boston to trade for Anthony Davis last season, it’s this rule that says you can have a maximum of two of these types of deals, but at least one must be a contract that you did not trade for.

If he were to sign a full max deal it could rise to as high as $201.8M over five seasons were he to make an All NBA team under the “Rose Rule.” These escalators are negotiable but since both a five year max and making All NBA seem unlikely we’ll bypass the remaining details.

Signing Brown to an extension would also change his cap value in terms of trades happening this season. If Jaylen were traded now he would count for his current $6.5M in salary for both Boston and the team receiving him. Were he to sign an extension, he would still count for that amount in outgoing salary for Boston, but would be valued at his average salary across all remaining season for the receiving team.

For example, were he to sign a four year extension for $80M an over-the-cap team trading for him would have to account for $17.3M in in-coming money but the Celtics would only get credit for $6.5M outgoing. This would make it much more difficult to trade him during this season.

Team Position

Having signed Kemba Walker to a max extension this summer, the Celtics are unlikely to be going under the salary cap next season. In order to get to the type of “max contract space” that makes it worth it to clear money, they would need to have Gordon Hayward opt out, lose at least one of Enes Kanter or Daniel Theis, and let Jaylen go.

While that is unlikely, this time last year it seemed even more unlikely that the team would be under the cap this offseason and then obviously they were. This is not a situation where signing Brown carries a clear opportunity cost in cap space, but it’s also not entirely meaningless.

The more pressing concerns might be around long-term tax obligations if Hayward discovers his pre-injury level and Jayson Tatum has a breakout season. A season a few years down the line with all of Walker, Hayward, Brown, and Tatum on big money deals would put them into the tax. If all those players are nice pieces who make a lot of money but don’t necessarily drive title contention that could be a problem.

The complications of trading a player signed to an extension are also a concern. With a number of options on the wing and Jaylen’s performance being up-and-down through his early career, the team could reasonably look to move him at some point before he hits free agency. If he were on a fair extension it would increase his value, but the mechanics become difficult.

Those other wing options also complicate the calculus. Ainge just invested the 14th pick in Romeo Langford, who plays the same position and will now be on rookie scale for four years. Carsen Edwards is small but more of a SG than PG and Semi Ojeleye is big but more of a wing than center. Grant Williams doesn’t look like Jaylen, but if Brown’s minutes at power forward for Team USA are a precursor to anything, they would start to be in competition for playing time, too. Even before getting to Hayward, Tatum, and Marcus Smart, the Celtics do have a lot of options to replace what Brown does.

If no extension is signed, Langford and Brown could be in, or perceive themselves to be in, direct competition for a long-term spot on this team. Will Brad Stevens handle that better than he did positional battles and contract pushes last year? Will that undermine team chemistry again? Those could be factors in wanting to get an extension (or trade) done just to avoid the headaches and give a clean slate in trying to re-establish a positive team culture.

The team also needs to evaluate what role Brown played in the culture deteriorating. It seemed like he and Irving clashed and while it’s easy to pin that all on Kyrie’s general weirdness, part of the job of non-star players is living with the weirdness of star players. Danny Ainge did praise Brown at the end of the season for his willingness to accept a bench role as the year progressed.

Player Outlook

As of now, Jaylen doesn’t have an agent, instead choosing to represent himself. It’s hard to read what that means here. Will he be less realistic about his performance than an agent would be? Is he less interested in winning a PR victory than an agent would be? Do either of those things matter?

After a year of clashing with Kyrie, not performing up to his own on-court expectations, and now seeing that same positional log-jam that the team has to evaluate, it’s fair to wonder if he even wants to be in Boston for the long-term. Irving is gone, but experiences can leave scars and emotions can linger.

If he does have half an eye on the exit, you need to look at who the suitors could be next year. The obvious choice would be his home state Hawks who will have a ton of cap space, a need on the wing, and a young team to build. The Grizzlies don’t project to have as much space but are in a similar position. Charlotte, Cleveland, and Phoenix may not be high on anyone’s destination list (aside from Terry Rozier) but they could all have money and a need. Toronto and possibly Portland could be more attractive destinations with money available.

In short, if Jaylen has a decent season there should be big offers available to him, even in restricted status, especially considering the weakness of the rest of the free agent class.

A final consideration should be how the Celtics have treated their RFA’s in recent seasons. While the team plays hardball in extension talks, they do not tend to carry that over into free agency. When it became clear that Kelly Olynyk was talking to Miami about a deal they wouldn’t match, they removed any barriers to getting it done. They probably could have squeezed Smart and forced a smaller deal but instead signed him at a fair number, as had happened with Avery Bradley a few seasons prior. Rozier moved to Charlotte via a sign-and-trade that, in the end, didn’t advantage Boston in any way but allowed him to get paid more than he would have anywhere else.

Considering the look of the 2020-21 free agency market and Ainge’s history in being fair to RFA’s, Brown should have no fear of going into that situation next summer.

Player Comps

What is Jaylen Brown?

This is a harder question to answer than it should be. If you flipped his second and third seasons his career arc would make perfect sense. Under this alternate reality, he came into the league as a raw offensive player with good defensive tools, took on a larger role in season two while still struggling with consistency but becoming a net positive contributor, then took off in year three primarily by improving his jumper. All of that would culminate in a breakout playoff performance, setting him up for a large extension.

Instead, that improvement showed up in year two and then regressed nearly back to his rookie level in the third season, which isn’t unheard of but is much harder to understand. Some of that may be related to his early season hand injury.

On offense he continues to suffer with tunnel vision, showing very little playmaking ability. His free throw shooting is also a concern; it’s easier to believe that he’s a poor shooter who sometimes gets hot from three than a good shooter from distance who can’t make 2/3 of his free throws.

Defense is harder to evaluate but the same trend of having a better 2017-18 than 2018-19 appears to exist. He’s never looked like a premier wing stopper but he is versatile and active; generating some steals and blocks while being prone to off-ball mental lapses.

In total, you have a talented player at a position of league-wide scarcity who can score and defend, though not consistently at the highest levels. He’s shown growth from his rookie season, but not on an easily projectable trend line.

The following comps are to players of similar size, age, and performance on a per 100 possessions and “advanced stats” basis in their second and third seasons.

The Max Money Players

Klay Thompson

Thompson is one of the great success stories of a modern front office correctly evaluating their own player, both in not trading him for Kevin Love and then coming to terms on a four year max extension in 2014 for 4 years and $70 million (from this point on contracts will be written like 4/$70M), equivalent to 4/$116M in 2020 cap dollars.

It wasn’t a lock that he would be worth that extension but as a true two-way player at a young age he was a good bet. At the end of their respective second seasons you could have argued that Brown was ahead of where Thompson was, and also younger. While Klay built on his success, Jaylen took a step back and so was a significantly less productive player entering extension negotiations. Were that not the case, Jaylen may have already signed a max extension like Ben Simmons and Jamal Murray.

Andrew Wiggins

The opposite of Thompson in every way but salary is Andrew Wiggins, who signed a full max 5/$148M extension in 2017, equivalent to 5/$169 now. This contract almost immediately became an albatross.

Of concern here is that Jaylen was a better player than Wiggins in years two and three and so may point to this contract as a reason he deserves the max, but also declined in year three like the Wolves’ wing. If he were to continue to mirror Wiggins, what’s a Rich Man’s Andrew Wiggins actually worth? Probably a lot less than he’d get paid.

Otto Porter Jr.

The Wizards did not extend Porter after his third season and ended up regretting it. After a solid-but-unspectacular fourth season as a 3-and-D supporting player in Washington, the former #3 pick received a max 4-year offer sheet from the Nets that the Wizards chose to match.

He was then paid around $40M by Washington to play about 120 more games before being shipped to Chicago for some expiring contracts named Jabari Parker (coming up) and Bobby Portis.

Porter is a decent comp for Brown in the abstract but, again, this is a player who improved from year 2 to 3, while also being more clearly a low-usage role player. A year that’s simply better than last year probably doesn’t earn Brown a max offer sheet in 2020 like what Porter got; he would need to show real development from his 2017-18 baseline instead.

Regardless, Brown may very well be anchoring his expectations to Wiggins and Porter, two of the more recent players on this list who were both top-3 picks in their own rights. One (undeservingly) got a max extension and the other (questionably) a max offer sheet. If Brown looks only at these two comps, he would reasonably demand a max extension of at least four seasons.

The Middle Ground

Jerry Stackhouse

In 1999, under a totally different CBA, Stackhouse re-signed for 7/$37M. That would roughly equate to a 4/$72M deal in today’s cap dollars, though the longer years and final season option in a time of flatter cap growth make something like 4/$90M a more fair comparison.

Corey Maggette

Maggette is a very different player stylistically but produced similar value. In 2003 he signed an offer sheet with the Jazz that the Clippers matched. That deal was for 6/$45M, equating to around 4/$74M in current cap dollars. Like with Stackhouse, you should adjust that up somewhat to account for length and league landscape.

T.J. Warren

A more recent comparable is Warren who signed an extension after his third season in 2017 for 4/$50M. Under the projected 2020 cap of $116M that would be a 4/$57.4M deal for Brown.

While Warren has similar productivity to Brown, and had a better third season than second, his “throwback” style on offense has always seemed to depress his market. He was also playing for a terrible team in Phoenix which can hurt a player in the restricted market, but in this case he didn’t even make it that far. Warren’s deal feels like the absolute basement of what anyone could call a fair offer for Brown; I seriously doubt that the Celtics opening offer would be as low as $60M.

The Downside Risk

Chase Budinger

This could be a cautionary tale for Brown as Budinger was a productive young wing who posted very similar stats and even participated in a Dunk Contest before a trade, health questions, and a season of disappointing performance tanked his free agent value. Following his third season he was traded for the 18th pick in the draft but after his fourth season he signed for just 3/$16M, equivalent to 3/$39.5M in 2020 cap value.

This is a reasonable potential downside if Brown were to forgo an extension and then have a bad or injury plagued season, particularly following a trade. Barring major injury he would still probably get more than that, having played far more minutes and with the prestige of being a high pick, but something in the Warren/Budinger range seems like a floor for what he could get in restricted free agency if he were to have a poor but somewhat healthy 2019-20 season.

Jabari Parker

Below the Budinger Line comes injury risk and market misreading. Parker was the second pick in the Wiggins-Embiid class but did not reach an extension following a procession of major injuries. Jaylen doesn’t have the same injury history, but injuries in season four are a risk for any player who turns down an extension offer after season three.

Parker ended up signing a 1/$20M contract as a high-upside flier in Chicago but was then traded for Otto Porter and is now on a 1+1/$13M deal with the Hawks that still seems like a significant overpay made because some people can’t get over the idea that a player was a high pick four years ago. That he’s been able to ride that high pick to functionally 3/$33M (3/$38M in 2020) despite those injuries and a general lack of positive play is another reason that Jaylen could feel emboldened to hit free agency.

Rondae Hollis-Jefferson

Finally, we come to the risk of getting into restricted free agency if you don’t have the residual glow of a high draft pick, even if you’ve been a relatively productive player. Like Warren, Hollis-Jefferson might suffer from being a throwback player (meaning not a 3PT shooter, basically) who made his bones on some bad teams.

After a strong third season that, in terms of offense/defense advanced metrics, wasn’t that dissimilar to Brown’s 2017-18, the Nets were waiting for the double-max cap space that brought them Kevin Durant and Kyrie Irving and so were not interested in signing extensions. Rondae’s fourth season was full of injuries and difficulty in finding a role and he now finds himself on a 1/$2.5M prove-it deal in Toronto.

It’s hard to imagine any scenario where things go this badly for Jaylen, but it’s not like RHJ had some outlier awful year in Brooklyn. He had a series of pretty normal injuries and struggles to fit into a system that led to a poorly timed lost season. This isn’t to say that not signing an extension could expose Brown to ending up on a minimum contract the following year, but there is a real downside of some significant amount when you choose to bypass “set for generations” money.

Prediction

I think the Celtics would be wise to get serious about extending Jaylen, despite the concerning third season. If they were to trade him now it would likely be for a player in a similar extension situation or for a future draft pick. You can never have “too many” future picks, but the Celtics do already have a deep roster of young talent and multiple future selections on top of their own. More than that, it doesn’t make a ton of sense to trade a high-upside and immediately useful player for a future pick when you have two 29-year-old max contract players on the books.

The team is unlikely to be a major cap space player in the next few summers so the opportunity cost is lower than it has been with recent extension candidates. Making Brown more difficult to trade in-season is a real drawback of extending him, but this team isn’t one trade from contending. In terms of high upside trade plays, the most likely way for him to return a big value would be by having a good fourth season with a fair extension locked in, not by being moved as an un-extended pending RFA. We’ve seen those players consistently have less trade value than conventional wisdom says they should.

While I think the upside play is to extend Jaylen, that doesn’t mean extending him at the max. If I were the Celtics, I would open with a bid of 4/$80M, get a little queasy at 4/$90M, and walk away around 4/$96M. He’s far from a sure-thing at this point and building a contending team is about signing surplus value contracts, not big contracts for exactly what a player is “worth.”

I don’t think Jaylen would accept even that fully guaranteed 4/$96M having seen players like Jamal Murray, Andrew Wiggins, and Otto Porter get max contracts in recent years. Even though it seems like a good time for the Celtics to break their “no extensions” streak, I suspect it will continue on for another season.

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