The first-round series loss to the Brooklyn Nets proved how far the Boston Celtics are from competing with the top teams in the Eastern Conference.
While one could point to the absence of injured All-Star Jaylen Brown, the Celtics were a .500 team all season and needed a play-in game just to reach the first round.
Now heading into the offseason, the focus in Boston turns to the rookie extension of Robert Williams III, the expiring contract of Marcus Smart and the free agency of Evan Fournier.
New head of basketball operations Brad Stevens faces a delicate balancing act as he moves from the sideline to the front office to replace Danny Ainge. Not only does he have to find his replacement as head coach, but he'll also have to try to improve a Boston bench that ranked toward the bottom in production with limited financial resources, a process that began early when he agreed June 18 to trade former All-Star Kemba Walker to the Oklahoma City Thunder for a package including former Celtic Al Horford. The move got Boston off the $73 million owed to Walker but cost the Celtics their 2021 first-round pick.
Jayson Tatum and Jaylen Brown
While some critics will argue that Boston needs to break up its All-Star duo as a way of reconfiguring the roster, that argument is a non-starter here.
If Stevens wants to try to move his two most valuable players and hit the button on a full-scale rebuild of last year's Eastern Conference finalist, that is his prerogative, but it would be a mistake.
Yes, the roster needs to change (we will get into that below), but Brown or Tatum should not be used as collateral damage as a means to balance it. Consider these facts:
Both are coming off a season in which they not only appeared in the All-Star Game but also played at an All-NBA level.
Both are still under 25 years old and have not hit the prime of their respective careers.
They play a position of value in this league; there is a waiting list of teams looking for young wings.
Brown is under contract for three more years and won't become a free agent until 2024. Tatum's rookie extension stretches through the 2025-26 season, though he can opt out a year earlier.
Those factors alone are a reason Tatum and Brown are not going anywhere, at least for this offseason.
Has the window to compete for a championship closed?
On the surface, the Celtics would seem to have a wide-open championship window, considering their two best players -- Tatum and Brown -- have yet to turn 25.
However, when you peel back the layers on the current roster and what the future holds, there is an argument to make that the Celtics' best days of competing for a championship are behind them.
Yes, the Celtics can chalk up the disappointment of this season to myriad reasons, including health. Stevens was forced to use 31 different starting lineups this season, after using 19 a year ago.
Starting point guard Walker missed 23 regular-season games, 18 with a chronic left knee injury. Evan Fournier, their prized acquisition in March, dealt with COVID-19 and appeared in only 16 games after the deadline. Brown was a symbol of durability in his first four seasons but missed 14 games this year because of various injuries (knee, shoulder and hip) before his season ended prematurely with a left wrist injury.
As a result, a Celtics defense that ranked in the top six each of the past three seasons slipped to 13th.
Certainly, injuries played a role, but was it the sole reason this team underachieved? If healthy, can Boston compete with Philadelphia, Brooklyn and Milwaukee next season?
The answer is no.
You can't be a win-now team and rely on a roster filled out with developmental projects who are not ready to compete at a high level.
That leads us to the offseason and the decisions Boston is faced with.
"We would definitely look to make some changes. ... How significant? We'll see," Ainge told the "Toucher and Rich" show in May.
The roster and finances
The true test this offseason is if the Celtics are willing to pay the luxury tax for a non-championship team.
"We have a 16-year record of spending and putting the best possible team out on the court, and I'll just leave it at that," Celtics co-owner Wyc Grousbeck told The Boston Globe in 2019. "Everybody can see what we've done, knows what we've done, and knows that we've put the Celtics first in every aspect."
The Celtics paid the luxury tax in a six-year stretch from 2007-08 to 2012-13 and once more in 2018-19. The $50.6 million in tax the team has paid ranks 10th among all teams since 2002-03. However, that was with rosters that featured a combination of Paul Pierce, Kevin Garnett, Ray Allen, Kyrie Irving, Al Horford, Gordon Hayward, Brown, Tatum and Terry Rozier. Do the goal posts move now that the Celtics are coming off a first-round playoff loss and don't appear to have a championship-caliber roster?
Heading into the offseason, Boston is already committed to $128 million in guaranteed salary and will be close to the $136 million tax threshold.
Re-signing Fournier, who was acquired using part of the $28.5 million trade exception Boston carved out in the Hayward sign-and-trade deal, likely pushes Boston into the luxury tax.
If Boston uses its $5.9 million taxpayer midlevel exception in addition to signing Fournier, the tax bill would increase to $35 million, before any kind of breaks given to teams as a result of pandemic-related declines in basketball-related income.
The tradable contracts and assets
Once you remove Tatum and Brown from any trade dialogue, Stevens and his front office are looking at a mixed bag of trade options. They were able to find a taker for Walker, bringing Horford back to Boston in the process, but it cost the Celtics this year's first-round pick. As for other players on the roster who could be moved this summer, here are Boston's options.
Expiring contracts: Marcus Smart and Tristan Thompson
Smart is the longest-tenured member of the Celtics' roster, and Ainge has made it clear how valuable he is to the team.
"Marcus plays as hard as anybody," Ainge said on "Toucher and Rich" after the trade deadline. "He competes at a level that -- he's won playoff series for us with his, I wouldn't call it bravado, just with his intensity and his competitive spirit."
Smart, who earned first-team All-Defensive honors in 2018-19 and 2019-20, is on an expiring $14.4 million contract but is eligible for a contract extension. Boston or an acquiring team (six months after the trade) can add a total of four years and $74.4 million of new money. If there is no extension in place, Boston would have a decision to make with regard to the future of Smart.
Thompson is on a $9.7 million contract and could be a financial casualty if the Celtics sign Fournier. The 30-year-old averaged the second-fewest minutes in his career (23.8) but still managed to put up 7.6 points and 8.1 rebounds. He had a +2.6 net rating in the 11 games in which he came off the bench.
Recent draft picks: Robert Williams III, Aaron Nesmith, Payton Pritchard, Grant Williams, Romeo Langford and Carsen Edwards
Boston has five former first-round picks on rookie contracts, plus Edwards, who was a high second-round pick in 2019. While the Celtics' front office can be critiqued on their draft history, they have done a solid job drafting in the 20s, most notably the selections of Robert Williams (27 in 2018), Grant Williams (22 in 2019) and Payton Pritchard (26 in 2020).
Out of the six youngsters, Robert Williams III has the most value and upside of the group. He started 13 games in the regular season and is a candidate for an extension this offseason, making it unlikely that Boston would move him in a deal.
The jury is still out on their former lottery pick Romeo Langford. Since the Celtics selected him No. 14 overall in 2019, the guard has spent more time on the inactive list as a result of injuries (and also COVID-19) than on the court. He has played in only 48 games his first two seasons but did see considerable playing time in the playoffs in place of Jaylen Brown.
If there was a positive to a rather disappointing season, it is that Aaron Nesmith got better from the first time he stepped on the court until the end of the season. Nesmith averaged a season-high 9.2 points in May, shooting 55.9% from the field and 50% from 3.
The trade exceptions
The Celtics were hard-capped this past season, making it difficult for them to use their large, $28.5 million trade exception. However, starting Aug. 3, Boston will no longer have to operate below the apron and will have four trade exceptions at its disposal to use: $11 million, $6.9 million, $5.0 million and $4.8 million.
But like the case with re-signing Fournier or using its $5.9 million midlevel exception, there is an added cost associated as it relates to the luxury tax to acquiring a player via trade using the exceptions.
The draft picks
Despite trading four second-round picks as a part of the Gordon Hayward sign-and-trade and the March trade to acquire Fournier, the Celtics still have second-round picks in 2021, 2022 and 2026.
Offseason cap breakdown
The Celtics avoided the luxury tax this past season when Gordon Hayward opted out of his contract, and stayed under at the trade deadline. With Tatum's extension kicking in this season, it's almost certain that Boston will be a taxpaying team in 2021-22.
With regard to the future, despite trading the $37 million contract of Walker in 2022-23, the Celtics are still projected to be over the cap.
Team needs
A big offseason of player development for the recent draft picks
Shooting off the bench
Wing defender
Stretch-4
Resources to build the roster
The draft: Second-round pick
Trade exceptions
$5.9 million taxpayer midlevel exception
Players on rookie contracts
Cash: $5.8 million to send or receive in a trade
Dates to watch
• Jayson Tatum's rookie max extension is scheduled to start at 25% of the salary cap ($28.1 million) in 2021-22. The total comes out to a projected $163 million over five years (he has a player option in the last year). If the $112.4 million salary cap in 2021-22 increases, Tatum will receive a bigger payday.
• Jabari Parker has a $2.3 million non-guaranteed contract. Parker has a July 31 trigger date that will see his protection increase to $100K. However, with the league year not starting until Aug. 3, expect that date to get pushed back. The salary will increase to $1.1 million if he is not waived by the first game of the regular season. After playing a season-high 15 minutes in each of his first three games as a Celtic, Parker collected six DNPs and has played sparingly.
• There are no offseason trigger dates on the $1.7 million Moses Brown contract. Brown currently has $500K guaranteed.
Restrictions
• The Celtics still remain hard-capped ($4 million below) until Aug. 3, the start of the 2021-22 league year.
• Tatum has a poison pill restriction that gets lifted on Aug. 3.
• The Parker $2.3 million contract counts as zero in outgoing salary until it is guaranteed.
• The Brown $1.7 million contact counts as $500K in outgoing salary in a trade.
• Tatum has a 15% trade bonus. The bonus would get voided if he is traded because it exceeds the maximum salary allowed.
Extension eligible
• Starting with Robert Williams III this offseason, Boston is set to see a parade of former draft picks eligible to sign a rookie extension. Williams has progressed from a project his rookie season (8.8 minutes) to a rotational player (18.9 minutes, 8 points, 6.8 rebounds) to the possible opening-night starter in 2021-22. He finished seventh in the NBA in blocks per game (1.8) this past season, a remarkable stat considering that he averaged only 18.9 minutes. Williams connected on 72.1% of his field goal attempts this season, with 208 out of his 258 shots coming within 5 feet, per NBA.com. In a Game 1 loss to the Brooklyn Nets, Williams came close to recording a triple-double: 11 points, 9 rebounds, 9 blocks. Williams is eligible to sign an extension for an additional four seasons until the last day of the offseason. The Celtics will need to decide if his upside is worthy of a new contract or if they need to see an additional season of work before committing to him long term. One thing to keep in mind: The last player to sign a rookie extension worth less than $10 million per season was Jeremy Lamb, who agreed to a three-year, $21 million extension with Charlotte in 2015. It's possible Williams would rather bet on himself than take what is perceived as a team-friendly discount, even if that means passing up on guaranteed money.
• In addition to Smart, Edwards is also veteran extension eligible. It is unlikely that he will receive a new contract.
The draft
The Celtics entered each of the past two drafts with three first-round picks, but they don't have one this year after trading it to OKC. They do maintain control of all their future first-round picks.
Here's how ESPN's Jonathan Givony and Mike Schmitz have Boston selecting in July:
No. 45 (own): Juhann Begarin | SG | Paris
The Celtics' three draft-night trades the past two seasons have been questionable. In 2019, the Celtics traded the No. 20 pick (the rights to Matisse Thybulle) for No. 24 and No. 33 (Carsen Edwards). They then traded No. 24 (Ty Jerome) and reserve center Aron Baynes to Phoenix for a future first-round pick from the Milwaukee Bucks.
That pick ended up as No. 30 last year, and Boston traded that pick (Desmond Bane) to Memphis in a three-team deal that sent reserve center Enes Kanter to Portland, a move that helped Boston avoid the luxury tax (and added two future second-round picks to their reserves).