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Celtics Offseason Preview Part 3 - Charting a Path

This is Part 3 of my 2020 Celtics offseason preview. In Part 1 I covered "the boring stuff" including CBA unknowns and level setting on basic roster moves. Part 2 covers how Jayson Tatum's ascension to "Possible Future MVP" level impacts the decisions made this offseason and into 2021.

Jayson Tatum's leap forward may be causing the Celtics' timelines to start diverging again, but that can't paralyze the franchise. Moves made this offseason will not only determine how far the team goes next year but also shape how the team sets up for that "second window" defined by Tatum's prime age seasons.


With both of those timelines in mind, we can finally start looking ahead to what the goals for this offseason should be.


Team Building Plans


Gordon Hayward

Not surprisingly, we start with the player who has defined so much of the success and failure of this Celtics mini-era. Hayward holds a $34.2M player option for the upcoming season but it's difficult to imagine him getting a new deal from anyone but the Celtics that would make opting out worth it. Maybe the Celtics would see enough value in cutting his 2021 salary to make the "lower annual salary, longer years" pitch to Gordon but with our established parameters of needing flexibility starting at the 2022 trade deadline, that isn't easy. You might have to spread the money out over four seasons to make the 2021 salary cut worth it to Hayward, and that would run the deal a season too far for the team.


The case for Hayward wanting to make a deal like that is actually stronger than the team's, in my opinion. If the model for next season's CBA is a large escrow withholding, pushing dollars out of that year and into future ones would let Gordon keep more of the paper value of his deal.

Boston might be willing to do something like 3/$60M but would Hayward do that when he's got $34M in a single season already signed? Under normal circumstances probably not, but a 30% escrow loss would equalize the first season by something like $4M. That still leaves Hayward agreeing to functionally a 2/$30M "extension." Given his age and injury history he might not get more than that in free agency after next season, but if he plays up to the level he did for this regular season he could better it by a significant margin.


If he is willing to restructure over three seasons instead of four, the salary and tax savings this season (it's conceivable the team could stay under the tax entirely with a restructure) might make up for what would be a very expensive 2021-22 campaign with Tatum's likely Rose Rule extension kicking in. He would also be a potential trade piece expiring at the same time as Walker.


If Gordon isn't interested in a three year re-write, the Celtics need to work hard on trading him. If he's healthy come playoff time, he's still a pretty good fit and unlocks a lot of options for the team, but his health isn't reliable and his contract is simply the wrong length. The franchise can't allow a $30+M deal to evaporate with two years left on Walker's contract and no cap space resulting from it. Letting him play out the deal would be too "all in" on a push for next season's title and the type of move that leads to a team aging out of title contention just as Tatum reaches the peak of his on- and off-court powers.


Gordon Hayward Trade Talk

There isn't going to be a perfect Hayward trade. Ideally you want a moderately sized expiring contract for a useful veteran plus a longer deal for a younger player with real upside or established trade-on value. It's hard to put all those pieces together and to get them you're going to have to move draft picks along with Gordon.


This always seems to start with the Pacers and Jared Weiss reported that his sources are saying Victor Oladipo is looking to get out of Indiana this offseason. Adding Turner to that package with the C's returning picks and/or maybe Indiana legend Romeo Langford does meet our contract desires. Oladipo expires after the season just like Hayward but Turner goes three more seasons on a manageable salary, expiring on the exact schedule that we want for Tatum planning.

The problem I have with this trade is that Walker and Oladipo would be a tiny backcourt, even with Oladipo's impressive wingspan. Oladipo also has all of Hayward's injury concerns and brings the most value as an on-ball offensive player on a team that already has Tatum, Walker, and Smart. He does have All NBA upside though; there are future paths where he stays long-term and makes Walker redundant.


I'm also not a fan of Turner but concede that many other people are and I don't have a monopoly on the truth. He can block shots and shoot but he strikes me as the ultimate regular season player. He's not strong enough to defend the likes of Embiid or Jokic and not mobile enough to help against Giannis, AD, or Adebayo. On offense the shooting is ok, but is any playoff defense going to respect a guy who has shot 36% over the past four years with a slow release and zero passing ability? Every team will ignore him until he starts the wind-up and then live with the results.


All that being said, not every team is striving to win the title and it's feasible that he's a rotation player for a few years and then at 26 or 27 years old, making 15% of the cap as a decent starting center, becomes central to the trade package for a new star pairing in that phase of Tatum's career. Brad Beal for Turner and some young players and picks isn't a wildly unrealistic outcome in 2022.


Part of the reason that the Pacers get talked about so often is that there simply aren't many other options. What teams could conceivably be interested in Hayward and even have the right contracts to move, regardless of if they're the right players?


Is three years of Harrison Barnes on a declining salary better than one of Hayward? Under the circumstances, maybe.


Aaron Gordon still looks like a good fit with the rest of what Boston would have if he's willing to accept what he is, but why would Orlando want Hayward now that Jon Isaac is missing next season? If Orlando were interested in pairing Gordon with Gordon instead, would the C's want to pay Nic Vucevic for three more years? Pairing Evan Fournier (if he opts in) and Terrence Ross gets the exact lengths and dollars of contracts we're looking for...


Is The Human Foul Machine Dillon Brooks worth a look? Would Dallas rather have Hayward or Tim Hardaway Jr. for one more season and Seth Curry for three, because that shooting would help the C's. Finagling Wendell Carter from Chicago seems unlikely, even if Otto Porter is included.


I'm somewhat of a fan of a package to New Orleans for Derrick Favors via sign-and-trade plus J.J. Redick but the S&T component creates all sorts of complications for Boston and to make the math work he would have to be paid more than he's probably worth on the open market.


There's a reason I thought that this past February might have been the time to move Gordon.


Marcus Smart

Part of the reason why I'm sketching the current title window as being two seasons instead of three is because of Smart. His deal extends two more years and if the team hasn't hung a banner in those years the difficult choice to let him move on might have to be made.


Smart is my favorite Celtic maybe ever so that's not something I relish writing. The reality is just that if the team finds themselves pivoting into a 2023-24 build, it may be short-sighted to re-up Marcus one year before that begins. He's going to make more than enough to make 30% max cap space impossible even with just he and the Jays.


Unlike with Hayward, who makes more and expires a season earlier, it's not necessarily the correct move to trade him, even if you are unsure about re-signing. With Hayward you're looking to get three years of lesser production in exchange for one; with Smart it would be only two seasons for one and at the likely peak of this cycle's title odds. A trade of Hayward is about cap management whereas one of Smart would be more purely about talent evaluation.


I would like nothing more than for Marcus to spend his entire career in Boston but precious few long careers play out that way.


2020 Draft Planning

It's no secret that the Celtics can't add three more rookie scale players to this roster. That's not to say that they must make a trade in a class where there seem to be multiple reasonable draft-and-stash options but it would be preferable to use at least one of their three first round selections to trade up, trade into the future, or upgrade with an incoming veteran.


I rarely advocate for trading up because of the poor historical value in doing so, but Boston is in a position where they should absolutely try to do it.


Part of this is psychological. The player they take might be most important as a developing trade asset, and players drafted more highly often hold some residual extra value over players drafted lower but who have produced similar actual value. If two years from now the C's are working out a Beal trade, it's just better to be offering a player who was the 8th pick instead of 14th, even if it's literally the exact same player who in that situation is then making more money.


In a weird way, the ideal outcome might be jumping ahead of Washington and Phoenix and then just taking whoever you think they like best to establish a "one who got away" mindset in one of those franchises in case you're negotiating for Beal or Booker down the line.


My own Draft Value Card pegs the combined value of the 14th (1,195 "points") , 26th (535), and 30th (385) picks as "worth" between the 5th and 6th picks. However, I've always thought that each subsequent pick added in the same draft needs to be discounted somehow so a more fair assessment is probably the 7th pick. In the Celtics position, I would take the 8th pick in exchange for all three. For 14 and 26 you should need to get 9 but I wouldn't complain about getting 10, as you can still always sell that player as a Top-10 selection.


Criticality of Non-lottery Player Development

Regardless of how this draft plays out, in order to walk this tightrope the Celtics under Stevens must get better at developing their own draft picks taken outside of the top-10. This is critical in part to support the current title push but also to give a pool of players who might be trade chips for the post-Kemba "third star." If the team goes the way of clearing the cap sheet and pursuing a max free agent in 2023, someone drafted in either last year's class or one of the upcoming two would be the most likely candidate to fill the bit of available room on top of Jayson and Jaylen, too.


For all that Celtics fans complain about Stevens's timeout usage, sometimes odd rotations, or overly-passive offensive system, the boldest red mark on his report card is the team's failure to develop their non-lottery picks. Brad deserves credit for the work done with Tatum, Brown, and Marcus Smart but further down the draft board it's ugly.

Under Doc Rivers, the Celtics consistently found value outside the lottery. No one is going to succeed with every mid-round or lower pick, and they went through a brutally bad timed fallow period after 2008, but Rajon Rondo, Al Jefferson, Kendrick Perkins, Delonte West, Tony Allen, Ryan Gomes, Glen Davis, Leon Powe, and Avery Bradley were all non-lottery picks who became at the very least solid contributors or positive value trade assets. Under Stevens, that list is basically just Jared Sullinger improving in Stevens's first year before plateauing and then dropping off the back-side of the cliff, Terry Rozier, and maybe Grant Williams.


The team can't both have a roster where one-third of the players are recent non-lottery picks but also rarely play those players in important situations. That's exacerbated by having two older undrafted rookies in Javonte Green and Vincent Poirier who basically never played. Half the roster was theoretical projects that Brad Stevens had little interest in investing non-garbage time minutes into.


That must stop if the team has any chance of contending now and still being in good shape as Tatum hits the point in his career where he can start exercising his will. If Romeo Langford ever gets healthy he needs to play and have a remit to do more than stand in the corner. Rob Williams can't be a "break glass in case of emergency" option next season; if he's on the team he needs to be on the floor for extended run in every game.


At the moment it looks like Tremont Waters has more potential than Carsen Edwards but whoever Brad prefers has to be given real minutes. Who he chooses is less important than that he chooses.


If Ainge doesn't move up, that same investment needs to be made in this year's picks. The lack of development from those lower picks is another reason why packaging them and trading up might be a better value for Boston than it would be in a vacuum.


Smaller Moves

While all of the bigger picture goals are important, what usually happens in that you can't find the necessary dance partners and so have to do the best you can around the margins. With that in mind, here are some small-picture ideas.


If Enes Kanter opts in, see if Portland wants him and Semi Ojeleye for nothing. The two together would fit into Kent Bazemore's trade exception. Portland is losing Hassan Whiteside and Kanter was productive for them in his last stint. They're also in desperate need for help defending big wings so Ojeleye is worth a look. Portland would have to send back a top-55 protected 2nd round pick to make this work but for Boston the real value is clearing roster spots and salary while creating two trade exceptions, with the one for Kanter's $5M potentially being useful at some point.


The team must have seen something in Vincent Poirier to give him above the minimum last year so maybe they still have plans for him in Year 2, but if not the Aron Baynes trade to Phoenix gives a template for how to move him out. Giving a team Poirier and either the 26th or 30th pick for a future 2nd rounder that projects to be in the top-45 would be fine. The receiving team would need to have cap space or an exception so the possibilities are limited. I don't like "selling" picks but in this case you're also buying a roster spot.


The Knicks have no one who ever tries to shoot threes. With their big guards they might be a good fit for Carsen Edwards and they have a trade exception from sending Marcus Morris to the Clippers. They own Charlotte and Detroit's 2021 2nd round picks so if the C's decide that they don't have minutes for Carsen, receiving one of those picks would be a good way to salvage things.


Cramming The Giannis Tangent in Somewhere


It's worth noting that the Player Empowerment Fear that will drive a lot of Celtics decision making in the first half of the 2020's can also create unexpected opportunities. In the unlikely event that Giannis declines to sign his super-max extension and hits the trade market, a package of Brown and either Hayward of Smart plus every young player or pick that Milwaukee wants and the ability to send back any contracts that they don't want, would be a highly competitive offer. I don't expect that to happen, but obviously if it were available Ainge would have to make a huge play for it.


Playing Out the Offseason


A "no major surprises" offseason that serves both the immediate title contention window and sets up the down-the-road pitch to keep Tatum in Boston for as long as possible would include moves that look like this:

  • Gauge Gordon Hayward's appetite for a 3/$60M deal to replace his final option year; if he is not interested, work hard to trade him in a 2-for-1+Pick(s) deal that returns at least one useful player whose contract ends after the 2022-23 season

  • Trade up at the draft and come out with no more than one full roster and one 2-way player for the upcoming season

  • As a secondary draft night goal, use one of the late 1st Round picks to move either Kanter (if he opts in) or Poirier while also adding a future 2nd Round pick

  • With Tatum showing more ball-handling abilities, and Walker and Smart already in place, elevate Tremont Waters and let Brad Wanamaker leave, with an understanding that backup PG is a spot that could be upgraded at the trade deadline if necessary

  • Decide if Rob Williams is your backup center and, if not, trade him, ideally for a protected 1st round pick 2+ years into the future

  • Try to trade Semi Ojeleye for a future 2nd round pick but when you can't get one, move on from him in the interest of forcing Stevens to play higher-upside options

  • MLE availability and budget fit is impossible to project without knowing the cap and tax lines and what other moves happen first

  • Sign Jayson Tatum to a five year extension with no option year, no matter how far you have to push the Rose Rule escalators

Beyond this offseaon...

  • No non-stars should be signed to contracts that extend beyond the 2022-23 season, even if it means passing on helpful players

  • Adding future picks would be extremely helpful as the team holds no extra future picks beyond this draft, but the further into the future the picks are, the better

  • Be more aggressive at the trade deadline than in recent seasons in support of short-term boosts to the title chase, knowing that you might be re-setting the whole roster in 2023 anyway

The Celtics are obviously in a much better situation today than they were at the conclusion of the 2019 playoffs. By far the largest factor in that is the development of Jayson Tatum and, while the acquisition of Kemba Walker and progress of Jaylen Brown are also important elements, all team planning does now start with him in mind. There is a window of contention now but every move has to be weighed against the importance of being in an ideal position for locking up Jayson's prime when that opportunity presents itself four years from now. It's not fair, but it is the reality of team building in the Player Empowerment Era.

Once the league announces how the 2021 season will work with cap and tax lines, I'll revisit with more specific cap math in tow.

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