This is Part 2 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 3 goes through some specific goals and decisions for this offseason.

I'm not going to go quite so far as to change the name of the franchise to the Taco C's, but that's about the only thing you could do to oversell the importance of Jayson Tatum to the Celtics' future plans.

In the Era of Player Empowerment, the Sword of Damocles hangs above any franchise lucky enough to draft and develop a player who looks like he's in the inner circle of those who will control the NBA title for their generation. Tatum, having made All NBA in only his third season and following that up with a playoff stat line that matches the best ever produced for a player his age, spent the past year establishing himself in that dangerous company.

Until relatively recently, drafting a player like Jayson opened a contention window for a franchise that could reliably extend over a decade. As long as a team was in a medium-sized or larger market and had not terrible management you could count on the league's rules and culture holding most elite players in place. That's certainly not the case any more. LeBron James, Kevin Durant, Kawhi Leonard, Chris Paul, Kyrie Irving, Jimmy Butler, and Paul George have all moved via free agency or engineered a trade at least twice each in their careers already. Anthony Davis is on his second team and would be on his way to Team #3 this offseason had he not already landed on the Lakers. Were they all healthy, that could easily be half the All NBA players in a season.

It's "unfair" to have to consider this already, but after only three seasons the Jayson Tatum hourglass is starting to release its first grains of sand. All plans that the franchise makes, starting now, have to heavily factor the timing of the rest of his career.

The "Two Windows" Tightrope

The challenge for the Celtics is a well established one. Having a player as good as Jayson makes you at least a fringe contender earlier than expected. That possibility of winning a title right away can't be ignored; no title shot ever can be. Aside from the immediate payoff, even if a team wanted to slow-play a build from that position they could risk alienating their franchise piece in a way that sows the seeds for their departure down the line, even if the decisions being made are meant to be to their benefit.

For that reason, the Celtics have to dedicate resources to a title push next year. Tatum is the central figure in their play but Kemba Walker and, possibly, Gordon Hayward are still major supporting players who are already on the downside of their aging curves.

The problem, obviously, is that there might be only a two season window that involves Walker. If you win a championship in those two seasons the rest almost doesn't matter. Boston may be Title Town in the 2000's but the Celtics have hung one banner in 33 years and the 2010's were an empty decade. A single banner is success by any reasonable definition for a player-team pairing; even one as promising as the Celtics and Jayson Tatum.

However, if you come out of these next two seasons without a title, Tatum will still be only 24 and Jaylen Brown only 25. If they're granted good health and luck they'll just be entering the primes of their careers and the team surrounding them has to be set up to support that.

How does any franchise serve those two imperatives? How do the Celtics in particular?

The Second Window Comes First

The reason that we start with Tatum is that it's his prime years that set the restrictions on what can be done in service of the immediate contention window. If we can define reasonable goals for the state of the franchise 3-4 years from now we can determine how far we can push the current roster.

As discussed in Part 1, a major challenge in every team's planning right now is that we don't even have a CBA for next season. Cap and tax figures are to-be-determined and technically the basic structures of the league are up for negotiation. We also don't know how COVID will be impacting the world down the line. It's conceivable that a widely available vaccine has the league playing in front of full arenas a year from now but that's certainly not a guarantee. Even were COVID not a factor, the NBA's current CBA was set to expire in 2024 but either side could opt-out following the 2023 season. This is exactly the time period we're concerned with here.

There's no good solution to this. All anyone can do it pick a reasonable path forward for the league and hope reality doesn't diverge so far from that as to make it impossible to adapt. In that spirit, I'll be assuming the salary cap stays at 2019-20 levels for next season ($109M), rises (via artificial cap smoothing) to $115M the following season and then grows at 6% annually after that. Thankfully, the national TV deal expires after the seasons I'm primarily concerned with here so unless COVID detonates that, there's one stabilizing factor at play. I'll also be assuming that the basics of contract structures, extensions, holds, etc. will stay how they currently are.

Using this conjecture, we can see that the 2023 and 2024 offseasons are our critical points for planning. Walker's contract expires following the 2022-23 season and at that time, assuming Tatum has signed long-term coming off his rookie deal, only Tatum and Brown are guaranteed to be under contract.

This sets us up the opportunity to go Super Team Hunting that summer but it's not at all easy to achieve. If Tatum's next contract is a Rose Rule deal paying him at or near 30% of the cap, just he and Brown and no other players under contract would leave the Celtics with less than 40% of the cap in free space in 2023. Considering that unrestricted max free agent deals start at either 30 or 35% of the cap, that leaves precious little room to carry other contracts on the books into that offseason.

Were the C's targeting a 30% max free agent that summer they would only have around $10M in available space for all other contracts and holds beyond the two Jays and incomplete roster charges. The only reason you can even get that far is that Jaylen is on what looks to be a below-market deal so trading him for a different player who could slot in as a "third star" on a super team is unlikely unless that player is on their rookie deal.

If you push this planning into 2024, Jaylen is already moving off his extension and onto a max-contract free agent cap hold where it's then impossible to clear 35% max space even with just the two Jays on the books, and a 30% max involves having functionally nothing but the Jays.

Is This Even Worth Considering?

The obvious reaction to that difficult cap math is to say that the Celtics should expect to not be a cap space team for the remainder of the time that Jayson and Jaylen are on the team and to plan accordingly. That may be how things play out, but in this era where players' eyes wander (completely reasonably, they are 20-something years olds and didn't get to choose where they were drafted), a way to keep them from growing tired of a franchise is to let them basically control the roster building at some point. That's not worth it for even perennial All Star-level players, but Jayson Tatum is tracking to be more than that and in the group that it is worth it for.

The Celtics brass cannot ignore that in 2023 Jayson's close friend and mentor Brad Beal could be an unrestricted free agent, if he picks up the final year of his current deal. That's also the year when Joel Embiid and Nikola Jokic would become unrestricted if either doesn't sign a super-max extension along the way. Giannis Antetokounmpo could also be hitting the market at that time if he bypasses the supermax with Milwaukee and instead signs a 2+1 contract elsewhere to bridge himself to the 10-year max tier. Kristaps Porzingis is scheduled to be in that 2023 class. If Anthony Davis follows the Klutch playbook he could easily be rolling year-to-year free agency at that point. Karl Towns and future Team USA buddy Devin Booker are in the more challenging 2024 group.

Beal is clearly the scary one here. He's a good player, a big-time scorer, and surprisingly young. He's also not really the level of player that you would want to gut your roster for, and certainly not if that roster-gutting would mean giving up on certain things during the immediate title window. Beal would also be in that 35% max tier as a 10-year veteran where things get brutally difficult to make work. Still, if Tatum does develop into a top-5 player can you risk trying to sell him on the idea that quality depth is more important than playing with his All Star best friend, particularly if teams in California, Florida, and New York are queuing up to offer him that?

The obvious out-card in that deck is acquiring Beal via trade before he ever hits the market. In this medium-term game planning, a way to do that would be Beal opting in to the final year of his contract and being traded for Kemba, who would also have to opt in. Little planning is necessary for that but there's a lot of moving parts there with two players having veto-power and likely additional teams needed.

A more realistic scenario might be trading Brown for Beal, a move that would substantially weaken the team around the pair but also one that the team would have to make if the alternative were losing an MVP-caliber Tatum. If Tatum and Beal want to end together somewhere in their careers, Boston is not necessarily the natural landing spot and that's the knife point extending down over Danny Ainge's chair.

The next star to play with Tatum of course doesn't have to be Beal, and could still be acquired via trade. It's likely that the reason the C's were so happy to send a full contingent of players to the 2019 FIBA World Cup was to establish Jayson and Jaylen in the team for future competitions where more of the top players are involved. We've seen the Team USA thread lead to other super teams and, while it's unfortunate that the other best prospects of Tatum's generation are mostly non-American, he will still spend a lot of time playing with the likes of Booker, Donovan Mitchell, and Davis. This is a double-edged sword where he could decide to team up elsewhere, but Team USA mainstays Tatum and Brown attracting a third Olympian to Boston is a reasonable path to title wins and contentedness for the Jays.

All of this requires building a roster over the next two seasons that is talented and flexible enough to contend for the title, attack the trade market through to the 2022-23 trade deadline, and keep open the possibility to clear the books almost entirely for a free agent play in 2023. Serving the dual goals of contending now and being ready to significantly re-tool the roster before Jayson's first chance at a super-max second extension in 2024 is the task at hand.

In Part 3 I'll look at how that could play out, starting with this offseason's critical decisions.