What now for Jayson Tatum, Jaylen Brown and the Boston Celtics?
After Boston's disappointing exit from the East finals, Celtics president of basketball operations Danny Ainge will use the offseason to assess the roster and manage a slew of draft picks.
Oh, and Tatum's contract extension talks are coming up, too, as the Celtics try to secure their main building block, get back to the Finals and win the franchise's 18th NBA championship.
Let's look at the various outcomes for the roster, free agency and the 2020 NBA draft for the Celtics.
Note: The financials here are based on the salary cap and luxury tax holding at 2019-20 levels as expected. Dates are subject to adjustment.
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The Jayson Tatum extension
If and when Tatum signs a max extension, he will join the likes of Ben Simmons, Jamal Murray, Pascal Siakam, Devin Booker and Karl-Anthony Towns as players who have signed a max extension since 2018.
The $158 million projected extension (based on a $109 million cap in 2021) will be the largest contract in Celtics history and the first time a player has signed an extension for the maximum in Danny Ainge's 17 years as the Celtics' lead basketball executive.
There are no benefits to waiting until the summer of 2021, when he would become a restricted free agent. Tatum is a franchise player, ranked No. 3 in the latest ESPN 25-under-25 (behind only Luka Doncic and Zion Williamson) and is coming off an All-Star season in which he averaged 23.4 points on 45% from the field and 40.3% from 3. He ranks 11th in ESPN's Real Plus-Minus this season and in the top 10 in win shares. He was named Eastern Conference player of the month in February after averaging 30.7 points in 12 games.
Tatum's $28.7 million cap hold combined with the $75 million owed to Jaylen Brown, Kemba Walker and Marcus Smart have the Celtics already over the cap in 2021.
Brown's four-year, $103 million extension was reached at the deadline last year, but Tatum's negotiations should go more quickly, with the main issues being a potential fifth-year player option and whether there is All-NBA language in the contract that would trigger an increase in salary.
Simmons, Murray, Booker and Towns signed five-year contracts without a player option. The four (along with Siakam) also had All-NBA language in the first year of the extension. For example, Simmons' contract will increase from 25% of the salary cap in 2020-21 to 30% (first team), 29% (second team) and 28% (third team).
The Tatum extension would not start until 2021-22, the year that Gordon Hayward will be off the books unless Hayward re-signs to a team-friendly contract. Signing Hayward would likely push the Celtics into the luxury tax for a second consecutive season and the third of four years.
Balancing the roster: draft, free agency and future finances
Boston has 14 players under contract (not including two-way players) and four draft picks this year (Nos. 14, 26, 30 and 47). That does not factor in restricted free agent Brad Wanamaker.
Here are the obstacles and possible options Boston has with regard to its roster:
1. Dealing with limited roster flexibility
Unlike last year when the Celtics had three open roster spots, that is not the case this offseason. The Celtics technically have 12 guaranteed contracts when you factor in the $5 million in non-guaranteed salary for Daniel Theis.
That leaves Boston having to make decisions about the non-guaranteed contracts of Semi Ojeleye and Javonte Green. Keeping both players would almost certainly see Boston having to make a trade with a player like Vincent Poirier or hoping that Enes Kanter opts out of his contract.
Last year Boston entered the draft with four picks and left with three players on the active roster (Grant Williams, Romeo Langford, Carsen Edwards) and a fourth (Tremont Waters) on a two-way contract.
2. Trading out of the first round for a future asset
Boston has established a pattern of consolidating assets. Last year, the Celtics flipped pick No. 20 to Philadelphia for Nos. 24 and 33. They sent the first from the 76ers and Aron Baynes to Phoenix for the 2020 first from the Bucks (acquired in the Eric Bledsoe trade).
Boston was trading No. 22 for essentially two valuable picks: a future first-rounder and the third pick in the second round. Trading Baynes also cleared cap space to sign Kemba Walker and Daniel Theis.
Of course, the downside is that Boston essentially passed on players like defensive stopper Matisse Thybulle (No. 20 pick) and All-NBA rookie first team Brandon Clarke (No. 21)
3. Packaging the Memphis pick (No. 14) and another first to move up in the draft
This is another form of consolidation and goes with the "quality over quantity" discussion that the Celtics will have leading up to the draft. It is also where the Celtics would need to trust their scouting department. For instance: What is the value of moving up to No. 10 to get the Phoenix Suns' pick? Is it worth picks No. 14 and No. 26? Or how about picks No. 26 and No. 30 for the Nets' pick at No. 19?
In 2013, Boston traded No. 16 and two second-round picks to move up three slots to draft Kelly Olynyk. (This is the same draft where Milwaukee selected Giannis Antetokounmpo at No. 15.)
This approach infamously backfired for the Chicago Bulls in 2014 when they traded Nos. 16 and 19 to Denver for the 11th pick. Chicago selected Doug McDermott while the Nuggets got two eventual starters, Gary Harris and Jusuf Nurkic.
4. Treating the draft as free agency
There is an argument to be made that the Celtics should keep all three first-round picks despite the roster crunch.
Because of Brown's extension that is set to begin and a likely max extension for Jayson Tatum that would start in 2021-22, plus Walker's max contract (which began last year), the Celtics will be limited as to how they add to their roster for the foreseeable future.
With three new players via the draft, the Celtics would have six young players earning a combined $20 million per season, or just $3.3 million per player. With that, instead of a revolving door of minimum-contract or tax-midlevel signees, Boston would have bench stability at a low cost.
Offseason cap breakdown
Barring a roster shakeup, Boston will be in the luxury tax for the first time since 2012-13.
Including three first-round picks, Boston has $150 million in committed salary, $17 million above the luxury tax.
The Celtics will have the $5.7 million tax midlevel exception available to use.
Depth chart
The resources available to build the roster:
The draft: Three first-round picks and a second
$5.6 million to send or receive in a trade
$5.7 million tax midlevel exception
Dates to watch
The tenure of Gordon Hayward in Boston has sometimes seen more heartache than accomplishments on the court. Signed to a four-year, $127.8 million contract in 2017, Hayward would miss his first season in Boston after suffering a dislocated left ankle early in the first game of the season. After some inconsistency upon his recovery, he eventually returned to form, but this season he sprained his right ankle in Boston's first-round series against Philadelphia, knocking him out of the playoffs. His deadline to decide on the fourth year of his contract is the day before the start of free agency (originally Oct. 17). A salary cap projected to stay at $109.1 million and his injury history will likely see Hayward opt into his $34.2 million contract.
Enes Kanter's role was greatly diminished in the postseason. Will that play a part in his decision? Should Kanter opt out and find a team where he has a more defined role, even if that means leaving money on the table? The center has until the last day before free agency begins to weigh that decision.
The restricted free agent tag is normally reserved for a player in his early 20s, not someone who is 31. But because Wanamaker spent the bulk of his career playing outside of the NBA and will have two years of service, the Celtics have the right to tender him a one-year, $1.9 million qualifying offer. The roster crunch could see Wanamaker as the odd man out.
There should be no internal debate about whether the Celtics should guarantee the $5 million contract of Daniel Theis. After coming off the bench in his first two seasons, Theis started 64 games this season, averaging career highs in minutes (24.1 per game), points (9.2), rebounds (6.6) and blocks (1.3). The contract becomes guaranteed three days after the moratorium begins (originally Oct. 21).
The $1.8 million non-guaranteed contract of Semi Ojeleye is set to become guaranteed on the first day of the moratorium (originally Oct. 19). The Celtics also have a team option with Ojeleye allowing them to decline it and make him a restricted free agent.
Restrictions
The poison-pill restriction for Jaylen Brown will be lifted on the first day of free agency. Because Brown signed a rookie extension last year, the average salary of 2019-20 and the new extension is used for incoming salary. For example, Brown would count as $22.7 million as incoming salary for a team acquiring him and $6.5 million as outgoing salary. Because of the restriction, Brown cannot be traded until after free agency starts.
Kemba Walker has a 15% trade bonus that is voided because it exceeds the maximum salary owed.
If Gordon Hayward opts into his contract and is eventually traded, his trade bonus is $4 million. The Celtics would be responsible for paying that amount and additional compensation would be added to his $34.1 million salary in 2020-21.
The Enes Kanter 15% trade bonus is worth $750,803. The bonus applies only if the center opts into his $5 million contract for 2020-21.
Extension candidates
Starting on the first day of free agency, the Celtics can extend Hayward for an additional four seasons. While they are restricted on the amount they can offer (up to $38.1 million -- a very unlikely amount) in year one, there is no restriction as to a percentage decrease in the first year. However, because of Tatum's expected rookie max extension, the Celtics are projected to already have $130 million in salary without Hayward on the roster.
Smart has two years left on his contract (at $13.4 and $14.3 million). The Celtics can add an additional three years and $55.7 million of new money. The first year of the extension in 2022-23 would coincide with the $100 million already owed to Kemba Walker, Jaylon Brown and Jayson Tatum. Smart ranked in the top 10 in Defensive Real Plus-Minus and win shares this season and would be 28 in the first year of an extension.
The Celtics can also extend Semi Ojeleye if his contract is guaranteed.
Draft assets
As discussed above, the Celtics have three first-round selections and one in the second.
Here's how ESPN's Jonathan Givony and Mike Schmitz have Boston selecting in the draft:
No. 14 (from MEM): Killian Hayes | G | Ulm
No. 26 (Own): Robert Woodard II | F | Mississippi St.
No. 30 (from MIL): Udoka Azubuike | C | Kansas
No. 47 (from BKN): Yam Madar | G | Hapoel Tel Aviv
Boston has its own firsts for the next seven years.