Danny Ainge wasn’t shy in assessing where the Celtics stand heading into another momentous offseason for the franchise last week.
“We’ve got some work to do,” Ainge said. “No question about it. I’m not overreacting to a tough loss to a good opponent. I’m just saying that there’s some things we tried to do, we’d like to do at the trade deadline that we weren’t able to do, and there’s some things I’d like to be able to do now, this offseason, to make our team better. But we have a lot to do.”
Ainge’s lack of wheeling and dealing at the trade deadline was done in large part to ensure the team had maximum flexibility this offseason to better improve for the future with draft picks and salary commitments. Logically, the front office likely figured Boston's championship window would open more after this season back in February. The assessment that the Celtics weren’t close enough to that contending window back in February to pay a high premium on trade assets ended up being a miscalculation due to a long list of factors.
With the Celtics bowing out in the Eastern Conference Finals for the third time in four years in what will be remembered as a very winnable series against the Heat, the pressure is now on Ainge and the front office after their non-action. The road only gets tougher from here in what will be an improved Eastern Conference from a health (Kevin Durant) and talent standpoint among top-tier teams.
The Celtics once long list of draft assets is now dwindling with no more future first-round picks owed to them from other teams beyond this season. Not only will the Celtics be on a level playing field from that standpoint with the rest of the league starting in 2021, but their good value contracts will be fading as well with Jaylen Brown and Jayson Tatum set to transition to pricy extensions in the next two years.
All of this puts a lot of focus on the here and now as the Celtics own four draft picks (No. 14, 26, 30 47) for the 2020 NBA Draft as the last remaining valuable capital on their roster beyond the team’s core players. If Ainge wants to keep his best five players together (a debatable stance) and still improve the roster (beyond a mid-level exception free agent addition), he’s going to have to properly leverage these picks at the NBA Draft next month.
There is no perfect answer to what the right answer is for Boston’s roster with those picks. Trading out of the draft for some future picks or veterans is a popular answer but the instant contributions of a Tyler Herro (No. 13) or Shai Gilgeous-Alexander (No. 11) over the past two drafts serve as an important reminder that hitting studs with non top-10 picks can happen and can help change the trajectory of a franchise from good to great.
The bigger problem for the Celtics though comes to roster construction and commitments.
Under contract for 2020-21
Kemba Walker ($34.3 million)
Gordon Hayward ($34.1 million – player option)
Jaylen Brown ($23 million)
Marcus Smart ($13.4 million)
Jayson Tatum ($9.8 million)
Daniel Theis ($5 million – team option)
Enes Kanter ($5 million – player option)
Romeo Langford ($3.6 million)
Vincent Poirier ($2.6 million)
Grant Williams ($2.5 million)
Robert Williams ($2.0 million)
Semi Ojeleye ($1.8 million non-guaranteed)
Carsen Edwards ($1.5 million)
Javonte Green ($1.5 million non-guaranteed)
Guaranteed: 12 (if Kanter, Hayward both opt in)
Non-guaranteed: 2 (Ojeleye (guarantee date at beginning of free agency), Green)
With Tremont Waters and Brad Wanamaker (both likely restricted free agents) expected to be in contention to stick around for an available roster spot, there is going to be a roster glut waiting