This is Part 2 of a look ahead to the Celtics’ future. In Part 1 I covered the basics and conventional wisdom. We’ll get further outside the box here…

Who Is Great?

We have a lot of good players but we need some great ones. -Danny Ainge, to The Boston Herald

Of the past 25 NBA Champions, 24 had at least one of these nine players: LeBron James, Stephen Curry, Tim Duncan, Dirk Nowitzki, Kobe Bryant, Kevin Garnett, Shaquille O’Neal, Michael Jordan, Hakeem Olajuwon. All nine of those players won at least one MVP in their career and all but Garnett (9) and Curry (4+) made at least ten All NBA teams. This is not a secret.

A few years back I made the argument that Ainge’s overarching goal as Celtics’ GM is to acquire transcendent star players. With that, I posited that the acquisition of Isaiah Thomas and absolute unwillingness to spend significant salary on very good players was all part of a multi-year play to pitch Kevin Durant on Boston. This “allure of the 1% chance” theory of franchise management traces back before Durant to the decision to execute the Nets trade, acquire Ray Allen to entice KG, trade a lottery pick to align contracts for a future KG trade, and even consider tanking when he “only” had Paul Pierce.

This theory, that Ainge’s only real concern is winning the title and that drives him to take low-odds chances at the absolute best players, has done a pretty good job of predicting his actions over the years. For that reason, I am somewhat uncomfortable suggesting that The Plan right now is to sign Gordon Hayward, or even sign Hayward and trade for Jimmy Butler. Does anyone really believe that Isaiah Thomas, Gordon Hayward, Jimmy Butler, and Al Horford make up a team good enough to beat the Warriors, who may be the greatest team in NBA history?

The idea that this is all about a player who fans just celebrated not making All NBA is just so… conventional.

If Gordon Hayward (or Blake Griffin) aren’t The Plan, then who, or what, is?

Forces At Work

Chicken or egg?

The first question to ask is: are those nine players inherently all-time greats, or do we perceive them as such because of their circumstances and the fact that they won titles. Did they drive the team to the title, or did the team’s success drive their career narrative? Put another way, could Isaiah Thomas be perceived like Isiah Thomas if you put three multi-time All Stars around him?

The answer to that seems to be an equivocal: Maybe. The King IN the Fourth undoubtedly just had one of the 20-ish greatest offensive seasons in NBA history. It’s possible that this theoretical team, with a healthy Thomas surrounded by three top-30 players, could steal a title in one of the transitional down periods that the league periodically experiences. The problem is that we are not (like, at all) in one of those periods right now.

When will the storm break?

The Warriors are three years into the greatest regular season run in NBA history, and they may still not peak until next season. LeBron James has made every Finals since the Reagan administration. The level needed to realistically win a title is as high as it’s ever been.

This is likely to last for at least two additional seasons. In San Francisco, Durant and Curry are going to re-sign and stay together for the foreseeable future. Draymond Green is signed for three more years. Klay Thompson is signed for two more. Looking forward, it seems like a fair bet that Klay could leave the Warriors in 2019-20. The luxury tax obligations that would come from carrying KD and Steph, plus possibly Draymond, on 35% top max contracts raising at 8% in an environment with slower cap growth, would have the team around the tax line for just those three players. Adding Klay onto that, and then trying to fill out a roster, seems financially unrealistic even for the Warriors. A team with KD and Steph at 31 and Draymond at 29 would still be formidable, but at least would be a “normal” core for a title winner.

Similarly, the Cavaliers have Kyrie Irving and Kevin Love locked up through 2019 (along with Iman Shumpert) and Tristan Thompson and J.R. Smith a year beyond even that. The luxury tax should start to bite into their roster in that same 2019-20 timeframe, and LeBron’s cybernetic body may also start to show wear when he’s 35.

How do you slay a giant?

It’s a pleasant fantasy to think that a well coached team of overachievers can take down these two NBA behemoths, but it’s not reality. Both of these teams were born from historic anomalies and it will take a third anomaly to lay them low. In that case, let’s start there.

Building a Super Team

If Danny Ainge only really cares about historically great players, then who has a chance to be historically great? Karl Town and Giannis Antetokounmpo aren’t going anywhere. James Harden and Russell Westbrook got special dispensation in the new CBA to keep them on their teams. Kawhi is too Spurs to not Spur. Kristaps Porzingis and Andrew Wiggins aren’t on the level; Joel Embiid is a phantasm. The obvious next in line for Danny Ainge’s lustful glance is Anthony Davis.

Brow Now

This is not going to happen. Don’t tell me that. I know.

If you actually want to challenge the Warriors next season you have to get nuts:

Draft Markelle Fultz Waive Tyler Zeller and Jordan Mickey Renounce Kelly Olynyk Trade Markelle Fultz, Jaylen Brown, Avery Bradley, and the 2018 Nets pick for Anthony Davis Make a three team trade with Al Horford going out and Paul George coming in Sign Guerschon Yabusele and Ante Zizic Sign Gordon Hayward Use RME and minimum contracts to fill out the roster

New rotation: Isaiah Thomas, Marcus Smart, Gordon Hayward, Paul George, Anthony Davis, Jae Crowder, Terry Rozier, Ante Zizic, Veterans on exceptions

You can look at that and say it’s impossible, silly, stupid, or all of the above. However, If I put Durant, Curry, Green, Thompson, Davis, Thomas, George, and Hayward into a pool for just next season and ask you to draft them in order, what does that look like? Warriors might still go 1, 2, 4, and 7. This crazy scenario is what it takes to get in a serious conversation about who is the better team with Golden State.

Is that scenario even remotely possible? Probably not, though you could make an argument that the Pelicans would be better off resetting than committing to Jrue Holiday and DeMarcus Cousins when Boogie and Brow play the same position come playoff time. If you’re the Celtics’ GM and you want to really push all your chips into the pot to chase a title right now, these are the kind of trades you have to find. Adding Gordon Hayward and Jimmy Butler doesn’t do it.

Davis Down the Line

A more likely plan is that the team starts triangulating for when Anthony Davis might actually become available, like they did with Garnett at the 2006 draft. At the moment, New Orleans is sticking with their current front office who are committed to trying Davis and Cousins together. If that doesn’t work, we could see a change in leadership in the next year. Depending on the philosophy of who comes in, it’s feasible that they could choose to reset things and make a major move. Only Davis and Cousins will have real value and Boogie will be a free agent so that may mean trading Davis and building a new team around the re-signing Cousins.

If that happens, the Celtics would need to have Fultz to dangle as the centerpiece of an offer. This is one reason that you cannot trade the pick for a 2nd tier star like Jimmy Butler who just leads you to a dead end. The trade is harder to do in-season because Bradley or Smart have to go in the summer for cap clearing purposes to get Hayward, but if you trade Bradley for a 2018 pick that could become part of the offer, with a different salary make-weight being worked in. The second part of moving Horford for Paul George (or similar) may not be possible in-season, but eventually the team will find that Davis and Horford together probably doesn’t quite work.

Assuming none of this plays out, you start planning for 2019-20 when NOLA may be up against free agency for Davis (though the DVPE could be a major factor) or simply be stuck in a prolonged period of wasting his prime. If they do trade him at that point, hopefully some of the young Celtics will have developed in a way to be better than him making it moot, or at a level like what Al Jefferson was in the Garnett trade.

Under earlier CBA rules, it would be tempting to start planning out for 2020 free agency already. Fultz, Zizic, and the 2018 Nets pick will account for ~$20M in salary that season. Add in the hold for only one of Brown or (theoretically) Hayward and you can make make space by accepting major free agent losses. There are two issues with this. The first is that, if Davis is healthy and a player worthy of doing this for, he’ll be designated player eligible and able to sign a much larger contract to stay in New Orleans. The other is that it requires limiting the next contracts for Thomas, Bradley, and possibly Smart to only two seasons (or finding future trades for them) and if you do that you may as well just commit to a full rebuild anyway, because those contract lengths aren’t happening.

All that being the case, it looks like there’s a two season window here where you call New Orleans every month to gauge where they are with Davis, knowing that if it gets to the summer of 2019 and he’s still a Pelican he’s probably about to sign a 5-year super-max extension to stay there, fulfilling the purpose of the new CBA. If you don’t believe there’s any real hope of prying Davis free before that, and you truly only care about winning the title, you’re left contemplating a different extreme.

Back To Go Forward

If none of the current or prospective prime-age Celtics are going to be as good as those nine title controlling players, then we have to force ourselves to start looking forward. The key season in our pivot seems to be 2019-20, when the Warriors could conceivably lose Thompson, LeBron will be 35, and this year’s draft pick (I’m just going to say Fultz) will enter his third season. Of the nine identified superstars, eight of them made the All Star Team by their third season. The other two were Curry, who was injured, and Dirk who somehow missed out on the All Star Game but made 3rd Team All NBA. In that year, we’ll know if Fultz has a reasonable chance to become that level of player, but to give him the best possible chance to succeed if he is, we have to commit in a way that assumes he will be.

Joining Fultz in that year should be Jaylen Brown in the final year of his rookie deal, Ante Zizic on a very cheap third season, and the 2018 Nets pick in year two. If all four of those players reach their “5% chance ceiling” then, as long as the team doesn’t trade any of them away, things will be great. You could make ten other bad decisions and still contend. However, banking on that scenario is a lower odds proposition than we should be comfortable with.

To maximize the team’s chances of opening the #Project2020 window it would be prudent to start adding future assets and avoiding out-year liabilities.

Flash Gordon

Here’s where we really re-introduce Hayward-based planning into the mix. If you think it’s possible to get Anthony Davis you obviously try to sign him, but what about if you don’t? I believe we have to start with an odd question:

Can you sell him on a “future based” sales pitch?

In mapping out future contracts, I can’t get around the idea that committing long-term to Isaiah Thomas, Gordon Hayward, and Al Horford makes it harder to open the Fultz-driven window of opportunity. That means that if what you sell Hayward on is “come and play with a team that just made the Conference Finals” you’re implying that you’re going to keep Thomas alongside him. Hayward’s new contract would be a 3+1 so it’s either bad and he opts into year 4, which is already in the window we’re trying to pry open, or he opts out and is a player you’ve either broken trust with or committed to in a way that limits team potential.

If, on the other hand, you believe that you can pitch Hayward on the idea that no one is beating Golden State and Cleveland right now then you can make the argument that he, by virtue of his age, development, and positional scarcity, is a key part of a Fultz-based future and not an Isaiah-based present. At issue, is that we might have to make this determination before ever speaking to him.

The Isaiah Paradox

For Isaiah, we have more than one question:

Is a three year max deal realistic? If you have to give him more than three years, how long does the deal retain positive trade value? What can you get for him right now?

While our targeted window opens in 2019-20, it doesn’t close then. We’re trying to build a wide period of opportunity around a hypothetical 10+ time All NBA superstar, so we do have some wiggle room in timing. If you believe that a max-$ three year contract is something that Thomas would sign to stay in Boston, I think it’s fine to keep him. He may not be a long-term fit with Fultz, but that deal would be tradable and he’s likely to still be a very productive player through the life of it.

If you don’t believe that contract is acceptable, you have to think very hard about if you believe he’ll be tradable in season three and beyond. If you don’t, you’re committing “title window assets” to seasons where you don’t have a realistic chance at achieving your goals, and it’s hard to bake an “under the tax” season into the plan so you can avoid repeater penalties.

Putting these things together, if you believe that Hayward would still be sign-able without Isaiah on the roster, and don’t think a three season deal is something Thomas would accept, and don’t think Anthony Davis will move in the next two years, the “right” thing to do is probably trading IT.

The issue now becomes value (and the heartbreak of trading him after the year he just had). The Warriors and Cavs are a roadblock to the whole league, so what team with any real future-looking assets would believe that they’re an Isaiah Thomas away from the title? The Spurs might actually be, but what do they have to trade? That leaves us searching for a team that wants to get better regardless of title reality. Do the Magic have a strong enough ownership “make the playoffs” directive to move Aaron Gordon and the 6th pick for a 2nd Team All NBA guard? Is the 9th pick and a future, protected Mavs selection enough to send him to Dallas? You end up in a position where trading him may be correct from a planning perspective, but it’s too hard to cut ties and the value proposition just doesn’t seem that strong.

Choose Your Own Adventure

Ultimately what we’re getting at here is a tough choice that we’ve known was looming for a year. The day after the Durant dream died, we could project to here.

The clock really starts ticking now. The team has until February 2018 to make the next major move or else this is a draft-and-develop rebuild with Horford and Isaiah Thomas hiding that reality. That’s fine, but probably not what Ainge is envisioning. If things drag out beyond that trade deadline we get to core pieces hitting free agency and the cap flexibility dries up.

The lower cap projections paired with the lottery victory have upped the stakes and moved the decision timeline forward. Your choices are:

Commit to chasing Anthony Davis for the next two years, knowing it’s a “1% proposition” that stunts future growth if it fails Trade Isaiah Thomas, hoping that you can still sell Gordon Hayward on the franchise’s future Get Hayward first, knowing that you will not go beyond three seasons for Isaiah and risk losing Thomas in free agency, or trading him at the deadline, alienating Hayward Walk away from the Hayward path, seeing him as “not good enough for this moment” and instead trying to tie up Isaiah via renegotiate-and-extend, by rule limiting the years to a length that aligns with the draft timeline Take the nuclear option and proactively trade Isaiah, Avery Bradley and Al Horford to put as many pieces on the draft timeline as possible

I simply do not see how the “conventional wisdom” path of signing Gordon Hayward and Isaiah Thomas to max contracts that extend obligations beyond 2020 is the correct thing to do if a title is your only concern. That route leads to substantial, long-lasting tax concerns, a stunting of player and asset growth in the window of opportunity, and a commitment of team economics, culture, and trust to a group of players who you don’t actually see as the core.

From a fan perspective I hate this conclusion. Isaiah is a wonderful performer and ambassador for the franchise. I like watching the team win games because it makes the long New England winter more enjoyable. I personally don’t see championships as the only redeeming quality of a team. However, if that is the only goal I’m given, this is where I land.

I don’t believe that all of Isaiah Thomas, Gordon Hayward, and Al Horford will be on the Boston Celtics 12 months from now, unless Anthony Davis is too.