Cleveland Cavaliers v Boston Celtics - Game Two

Can Danny Ainge stay patient in a summer full of opportunity?

Coming off a Conference Finals season, Boston has more assets than any other team. What do they do with them?

With the NBA Draft being the socialist vehicle that it is, rare is the day that the team in Conference Finals contention picks near or at the top of it. After all, by the draft’s very design, the good teams pick at the bottom. To be good and still pick towards the top takes a good trade, or some good luck, or normally both. The Boston Celtics certainly enjoyed that combination of good trade and good luck when they flat out fleeced the Brooklyn Nets in the July 2013 deal that saw Paul Pierce finally leave Boston.

In that deal that saw them trade away Pierce, Kevin Garnett, Jason Terry and D.J White, Boston received five players, yet none of note. Of all of Kris Humphries, Gerald Wallace, MarShon Brooks, Kris Joseph and Keith Bogans, only Wallace stayed with the team for more than a year, and even then, that was merely because his contract was too big to easily disappear (they were able to shift it in the end only when it was expiring, and only then for an even bigger expiring one in David Lee). Humphries lasted one year before leaving via a sign-and-trade for a protected second round pick that never came, Bogans lasted one year but only played 55 total minutes, Brooks lasted six months before being the token outgoing piece in a salary dump that saw the Celtics secure yet another first round pick and yet another second round pick, while Joseph lasted only three days. With no incoming players of note, that trade, and all the ones subsequent to it, were about the future.

With the number one pick in the upcoming draft, that future could here now. Much like when the 2002-2003 Detroit Pistons, fresh off a 50-win season and their first trip to the Eastern Conference Finals in more than a decade, picked up the #2 pick in the following month’s draft due to an archaic and highly one sided trade with the Memphis Grizzlies, the Celtics are going to pick first overall in three-and-a-bit weeks’ time, despite the 53-win season and Conference Finals season of their own. Hopefully, they’ll do better with it than Detroit did with Darko Milicic.

NBA Finals Game 2: Detroit Pistons v San Antonio Spurs

In the Pierce deal, Celtics President and general manager Danny Ainge let Nets general manager Billy King badly overpay him, mortgaging the Nets’ future for the immediate gains of declining veterans. With no other team really in the running, King consistently outbid himself, and Ainge ended up with a feast – first round picks in all of 2014, 2016 and 2018, all of which were completely unprotected, as well as the right to swap picks in 2017. It is that right to swap picks that will see the Celtics pick first next month, as well as having previously picked 17th in 2014 (James Young) and 3rd in 2016 (Jaylen Brown), along with who knows where next year. Pierce and Garnett, meanwhile, have long since departed the Nets.

Just as Ainge was patient in those negotiations, allowing King to keep tickling his own bid upwards, he has remained patient at every turn since. That one trade is what put the hitherto-scuffling Celtics in an extremely asset-rich situation, and Ainge’s moves since have been designed to keep them there. Very rarely have they made moves that dealt future assets in the form of draft picks in exchange for the immediacy of players under contract; the lone significant time that it happened, trading the first round pick that eventually became Skal Labissiere to the Phoenix Suns in exchange for Isaiah Thomas, was one of the best deals of a generation. Patience followed by timely underpayments is the perfect recipe for rebuilding without tanking.

At the most recent trade deadline, Ainge remained patient. We can never truly know from the outside whether they truly were, yet rumours abounded that both Chicago Bulls swingman Jimmy Butler and Indiana Pacers forward Paul George were both plenty available at the trade deadline for any team willing to part with the right future assets. Both would have merited paying a premium, Butler especially, and few teams with quality draft assets potentially would or could be considered likely or sensible to deal them for an incumbent star. (The L.A. Lakers, for example, could not get a deal on a quality draft pick that they could not be sure at the time that they would even have had, given the protection on it that meant they did not know they had it until the results of the lottery.) Teams with high draft picks generally do not seek to trade them for one star because teams with high draft picks generally are still on the way down, and need a foundation of talent beyond that one player before they can think that way, a talent foundation best obtained from multiple years near the top of the draft.

The Celtics were the rare exception, and so all eyes fell onto them. Yet even if it was true that George and/or Butler were available, and even if it was true that Ainge could have had them had he parted with the Nets pick, he did not do so. To the frustration of much of his fanbase, and myself, Ainge kept the pick, supposedly so with his eyes on drafting Washington’s freshman guard Markelle Fultz.

And again, the patience has paid off. Having won the lottery and the right to pick first, Fultz is now Ainge’s if he wants him.

Boston Celtics Media Day

Whatever direction Ainge chooses to go with the #1 overall pick, with the draft in general, and with the summer as a whole, it seems highly likely that the Celtics will still stay relatively young. They are already the sixth youngest team in the league, and they are about to have four more draft picks, at least the first of which is going to immediately join the team.

Even if the #1 pick were to be traded – and, it should be remembered, #1 overall picks are extremely rarely traded – Ainge still has young reinforcements coming in the form of 2016 first round picks Guerschon Yabusele and Ante Zizic. Indeed, Yabusele spent part of last season with the Celtics’ D-League affiliate, the Maine Red Claws, thereby being as directly involved with the team as he could without being under contract to them. The 20-year-old Zizic meanwhile played his first ever Euroleague minutes with Turkish side Darussafaka last season, looked thoroughly capable in them, and will have Tyler Zeller’s roster spot someday very soon. The Adriatic League is pretty good, yet Zizic was way too good for it, hence his mid-season move to Darussafaka and the Euroleague. Between the two players, there’s a lot to like there.

As evidenced by the selections of Yabusele and Zizic, the rare first rounder draft-and-stashes, Ainge’s patience is not simply something manifest through a lack of consolidation trades. At a time that many of the future picks he has long traded for are starting to come to fruition, Ainge remains patient in his execution with them; the eight picks he had in 2016 yielded only Brown and Demetrius Jackson immediately, and included three draft-and-stashes (including the aforementioned duo plus Abdel Nader in the second round), with two other second rounders being traded for a 2019 first round pick from Memphis. Although once rumoured to have offered six picks for the Charlotte Hornets’ 2015 first rounder which they eventually used on Frank Kaminsky but which the Celtics would have used on Stanley Johnson - suggesting he will change gear if he ever finds anyone worthy - Ainge was prepared to play the long game in last year’s draft even when knowing his team would be a playoff team this season.

By virtue of their best player being so comparatively underpaid, the Celtics also have the opportunity to make some waves on the free agency market this summer. This season is a pretty good one for free agents; some elite names on the market include Gordon Hayward, Blake Griffin, Chris Paul and Kyle Lowry. Hayward in particular has long been thought of as a likely candidate for the Celtics, on account of the fact that joining would be a reunion between himself and his former head coach at Butler, Brad Stevens. A bit of cap fiddling could get the Celtics as-near-as-is maximum salary cap space this summer, a rare repeat feat having also done so last season in the successful pursuit of Al Horford. And it will not take much cap manoeuvring to do it – the renouncing of free agents alone is essentially enough.

They have, then, plenty of options. Perhaps more than any other team in the league. Armed with the combination of the high pick, the hitherto-unmentioned three second rounders, the 53 wins, the Conference Finals run and the cap space, the Celtics might be the one team in the league capable of getting anybody that is available this summer. That is truly what it means to be asset rich.

So, what on Earth do they do with it all?

Cleveland Cavaliers v Boston Celtics - Game Five

If Ainge’s modus operandi in the systematic dismantling of the championship winning Big Three Or Four Depending On Your Feelings Towards Rajon Rondo has taught us anything, it is that he will try to both have his cake and eat it. Or at least, he will if the roster spot situation permits it. The downside to all this patience and asset accumulation is that there are a finite number of places to put people.

After the trade deadline, in which Ainge once again sat on his assets, I remarked upon this roster crunch thusly:

Since the natural dismantling of the title winning team of a decade ago, Boston Celtics President of Basketball Operations Danny Ainge has been consistent in an asset-accumulation strategy.

Rarely in the past five years have the Celtics been the team giving away the future asset, be it the draft pick or the draft rights or the young player under contract. They have instead sought them all. Indeed, they have sought so many of them that they are starting to run out of places to put them.

2015 first round pick R.J. Hunter was cut this past training camp after only one year in the league due to a lack of roster space. Hunter was fighting for a spot with 2014 first round pick James Young, another first rounder on the cusp of being cut, neither of whom had had any playing time in the year prior or figured to have any in the immediate future.

Further to that, 2016 second round pick Ben Bentil was cut before his rookie season tipped off, and within weeks of signing a three-year contract, due to the same roster crunch.

Even last summer, then, they were running out of space on the roster. And that is not going to get much better with another full draft slate and free agency period to come. The introduction of two-way contracts from next season as a part of the new Collective Bargaining Agreement will help, and perhaps avoid more Hunter/Bentil situations, but the decision to keep onto some many assets and obtain yet more draft picks even when somewhat competitive and planning significant free agency splashes has made this roster crunch inevitable.

Brooklyn Nets v Boston Celtics

Ainge’s patience, though often virtuous, has created this problem. Of course, it is in isolation a comparatively mild problem. Jordan Mickey is an athletic and projectable forward worth having, but if his roster spot is needed, he is an easy cut. So is Jackson – likewise, a good prospect, but not an obstacle. Other non-essential pieces could be easily moved, be it by trade or waivers, and none of the upcoming free agents (Young, Amir Johnson, Jonas Jerebko, Gerald Green and Kelly Olynyk) really need to be back, with only Olynyk having any value of note down the road (and perhaps Johnson too if his health holds up). It does speak, though, to the fact that the Celtics stand at a crossroads. Having played the long game in the rebuild and forgoing the nuclear option, Ainge now wields the benefits of his patience, but he also must start firing more bullets.

The trade for Thomas and the signings of Johnson and Horford signalled an intent to start to strive forward, yet the Celtics are suitably far along in the rebuild that it no longer counts as one. Given that it is no longer a rebuild, the strategy must also move to the next step along. For the Celtics of the now, things may have reached the point that The Deal for The Star is less about making the leap to the next level, and more about asset consolidation. There will neither always be opportunities to do the Rade Zagorac/Devonta Davis for a future first-type deals going forward, nor much purpose in doing so. The can cannot be kicked forever.

Given these conflicting desires to patiently acquire assets yet ultimately get somewhere with them all, dovetailing in a summer when they have better assets than ever and yet increasingly little space to use them on, can Ainge still have his cake and eat it? Can the same strategy persist without suffering from diminishing returns, or must all the eggs go into the one basket now?

Boston Celtics v Phoenix Suns

The Celtics do at least stand at those crossroads with their arms full of weapons. The immediate future depends on how patient Ainge wants to be, and which path that results in. They could, in theory, go ‘all-in’, or at least close to it. But to do so would assume they were close enough to the top to merit doing so.

A slight comparison can be drawn, in a sense, between the July 2017 Boston Celtics and the July 2014 Cleveland Cavaliers. Cleveland had come off a very poor season, and won their #1 pick the traditional way. Nevertheless, the Cavaliers at that time had both the first overall pick and maximum cap space. And although the draft pick came first, the free agency signing commitment from LeBron James the following week suddenly meant the pick was not as important as it was before it was made.

Thereafter, it became the priority to get LeBron whatever he needed to win. Cleveland already had Kyrie Irving, and while Irving had work to do on his game, he and James were thus immediately anointed two of the increasingly-customary Big Three Stars that is now essentially required for winning titles. Star number three was required.

Andrew Wiggins, the player they had chosen with the first overall pick, could have become the third guy. But waiting for him was to be waiting for too long, and waiting unnecessarily. Wiggins was dealt with spare parts to the Minnesota Timberwolves for Kevin Love. And it was the correct decision – two years later, the two moves in tandem did indeed win the Cavaliers that very title.

Cleveland Cavaliers v Boston Celtics - Game Five

Just as Cleveland had Kyrie, Boston has Isaiah Thomas, plausibly one of the three players in a Big Three. The Cavaliers had a #1 pick and max cap space, signing one Big Three-er via free agency and dealing the #1 pick for immediate gains when they could. Boston has the same, and could thus theoretically do the same. To do so would essentially be going all-in.

Of course, though, that one Cavaliers signee was LeBron. His transcendent talents gave the Cavaliers the opportunity and incentive to trade the future for the present in the way that none of the choice free agency names this summer – Kevin Durant and Steph Curry excepted – can do. [The unlikelihood of attracting those two is why they did not make the list above. It is hereafter assumed impossible.] Good as he is, Gordon Hayward is not LeBron. Signing him would not likely put the Celtics into that sphere.

Isaiah Thomas is also not LeBron James. Indeed, Isaiah’s future may determine his team’s future. While trading the #1 pick for an incumbent star might not make sense without being able to concurrently sign LeBron James, trading Isaiah might.

Cleveland Cavaliers v Boston Celtics - Game One

The beauty of a rebuild, especially one as considered and opportune as Boston’s, is that it allows a team to target the exact pieces it wants, and to find pieces that fit. A clean slate allows for such decisiveness, clarity of thought and cohesive visions, akin to drawing on a blank piece of paper as opposed to a dot-to-dot puzzle. However, if Isaiah remains with the Celtics, the Celtics must then implicitly find pieces to go with him.

Part of the problem with that this summer will be the question of timing. A lengthy look at the abilities of Fultz, Lonzo Ball, De’Aaron Fox and the other top prospects in the draft is not fit for this space. What is of note though is that those three are all point guards. Of all the years to have a first overall pick in, having it in the Year of the Point Guard when your best player, sole star and offensive lynchpin stands only 5’9 is rather unfortunately timed. The same is somewhat true in free agency, as it is also the summer of Chris Paul’s free agency (the available best free agent with a reasonable chance of leaving his team), and Paul and Thomas would not work. Ainge could in theory reach or trade down for Jayson Tatum, Josh Jackson, Malik Monk or Jonathan Isaac, yet to do so negates the value of the #1 pick – as seen above, the Celtics need a couple of star players, not a few good ones. And of course, such a discussion may be irrelevant anyway - the story remains that Ainge’s eyes are set on Fultz.

If Fultz is the pick, he is a tough fit alongside Isaiah. Despite the size, frame and wingspan to very much handle the shooting guard spot – he is already bigger than, say, Gary Harris - Fultz is a point guard by trait and by design. He is a scoring, ball-dominant point, and while he is a good catch-and-shoot player as well, were he to take on that role, Avery Bradley’s use and value to Boston is now mitigated. Similarly, were Fultz to start as a sixth man, Marcus Smart would now be squeezed out. And so on. There are diminishing returns that having yet another guard on board might bring, despite the clear-cut #1 pick candidates all being guards. While a team should always want to draft the best player available with every draft pick they have, and especially so with a first overall pick, Boston’s self-determined best player available jars awkwardly with the roster they have, and decreases the value of both himself and the incumbents. They are not asset rich enough to ignore that at a time that they need to source elite, cohesive talents.

Washington v Arizona

As a lynchpin to his team in its current guise, Isaiah has clearly defined strengths and weaknesses. Most obviously, he is an elite scorer. Thomas is so adept at getting inside the paint and finishing, even when so undersized, that he can score on every opponent and already has. He also continues to develop as a playmaking point guard; the fact that he always has been and always will be a score-first player works in his favour as he develops stronger understandings of how to use that defensive attention to keep defences off-balance, find shooters, move the ball, hit the big men in the post and the pick-and-roll, and make good decisions. The Celtics are much better with Isaiah. Any team would be much better with Isaiah.

Conversely, however, he is also one of the least impactful defenders in the league. The Celtics almost always run at least three of Marcus Smart, Avery Bradley, Jae Crowder and Al Horford in various combinations alongside Isaiah when he is in the game, because all four are plus defenders with ball pressure and switching ability who can counteract Thomas’s individual shortcomings. But aside from Horford’s passing - which is more willing than it is particularly incisive – there are no regular offensive creators amongst that bunch, and the need for Isaiah to do it all on that end is one of the biggest problems that caps the Celtics at the talent level that they are at. He cannot just be flanked with defenders. He needs more scoring help.

In the context of Thomas’s legitimacy as a cornerstone, more important than who he is flanked with is just how ineffective as an individual defender he truly is. Of the 468 players with enough minutes to qualify for ESPN’s Defensive Real Plus/Minus stat, a stat which tries to calculate how many points better or worse off a player’s team is on either end of the floor per 100 possessions when that player is in the game, Thomas’s -4.07 rating ranked dead last. And it is last by quite some way, too; only 10 other players scored less than -3.0, and only Doug McDermott’s -3.92 also ranked worse than -3.42.

For context, Isaiah’s Offensive Real Plus/Minus rating ranked sixth in the league, a testament to his elite offensive skills. But he scored only +5.66 on that end, for a net RPM of +1.59, 67th in the league, one spot behind Jeff Teague. He is not quite giving away as many on the defensive end as he does on offense, but it is much closer than it needs to be. To counteract this, Boston therefore requires some star-level scoring talent that also at least breaks even defensively. They need to add elite scoring without detracting much from a defence that already has one of the league’s worst defenders on it and has to compensate at every other spot. They need an elite two-way player or two. And as replete with assets as they are, that is an incredibly tough ask.

Cleveland Cavaliers v Boston Celtics - Game One

This is not an argument that Thomas should have his role reduced, in deference to Fultz, Paul or anyone. This is not Jason Terry, Jamal Crawford, Brandon Knight, or one of any other number of small guards best at scoring who seem to invariably get defaulted to being sixth or seventh men. Thomas is several tiers above that and should remain so. Very, very few score better than him, and thus he should try and score more than all but the very few.

This is also not an argument that Thomas, with his playing style and size deficiency, can never be a winner in the NBA. That argument exists, yet that argument exists in a vacuum that team building never ever does in practice. You could win an NBA title with Earl Boykins, Rick Brunson, John Fashanu or Judi Dench as your point guard if everything else is good enough. Some players are more cohesive to title-winning teams than others, certainly, and given the defensive deficiencies he can probably never overcome, it might be hard with Thomas. But it is possible with anybody, and certainly with someone so good. Isaiah Thomas on the San Antonio Spurs, for example, would make for quite the competitor.

However, it may be fair to say that the Boston Celtics in their current guise are not the perfect combination of pieces required around him, and nor might they be even after this offseason.

That current guise is in large part to Thomas. Nothing that has happened or that will happen is his fault, but insofar as being very good yet not elite can be considered a problem, Thomas might not be the solution. Just as they are at a crossroads with their overall basketball operations strategy, then, the Celtics might be at something of a crossroads regarding the medium and long term futures of Thomas. Even with all the weapons in their arms and all the bullets in the gun, the path to flanking Isaiah with the pieces needed to get to the NBA Finals that does not involve merely waiting for LeBron to retire is not an obvious one, one made difficult by Isaiah’s own shortcomings.

That does not mean they should not try, obviously. But it should be remembered that, despite a relatively poor playoff performance for understandable reasons, trading Isaiah right now would mean trading him when his value is extremely high. Isaiah Thomas is a 28-year-old filthy cheap two time All Star, elite scorer and fourth quarter closer. If he is not the right piece for Boston going forward, he will absolutely command the value of someone that might be. Ainge has come out this week and said that Isaiah will not be traded. Yet this statement does not mean much. Especially since the message, quoted verbatim, was thus:

[…] But we want to keep Isaiah. All I know is that he’s had an amazing year, and who doesn’t want Isaiah Thomas on their team?

Exactly. And therefore, there’s a market for him.

2016 Continental Tire Las Vegas Invitational - Vanderbilt v Butler

Irrespective of what does or does happen with Isaiah Thomas, though, Danny Ainge still has his other options. He always has his options.

We have seen some of his options above. We have seen how good his pick is. We have seen some of the candidates he can pick with it. We have seen the money he has available to spend. We have seen some of who he can spend it on. We have seen how patient he is, how pragmatic he is, how good of timing he has, how good of value he invariably gets.

In the LeBron era, we have also seen that this good Celtics team is not good enough, and that success with the number one pick notwithstanding, there is nothing incumbent on the roster not readily available that will tip that balance. Not unless Jaylen Brown can get elite ball skills to go with those physical tools. Not unless Marcus Smart plays every game like it’s game three of the Conference Finals.

The awkward reality for the Celtics is that, while this is no longer a rebuild, theirs is also not a team especially close to the cusp. Care has been taken in this space to pay respects to a fine season – 53 wins, number one seed, Conference Finals run – without using language that suggests an NBA title shot was ever truly on the cards this season. It wasn’t. The Celtics were under-talented even with Isaiah and never looked like winning the NBA title.

Cleveland Cavaliers v Boston Celtics - Game Five

But they knew that. Ainge’s refusal to move at the deadline was done with this summer in mind. The asset accumulation of years prior became a strategy of asset preservation come February time. After the trade deadline and Ainge’s (supposed) refusal to make a trade for a star, I wrote the following:

As valued and logical as asset accumulation is, especially by this author, it is an aim for the poor and the mediocre. As described above, and here in a critique of Sam Hinkie's time with the 76ers, it ultimately has to come to something. If not already a title contender, the best position for a team to be in is when in the mid to high playoff seeds, on the cusp of the top tier, with the youth and/or assets to make the leap attainable. When Boston was the mediocre, rebuilding team, prioritising asset accumulation made sense. But they are too good to default to it now.

This remains true, if not truer still. Boston are too good to prioritise asset accumulation any longer. The roster spots are dwindling, and, lest it not be forgotten, even the most successful youth movements around the league struggle a couple of years down the road when everyone suddenly needs big contracts.

Similarly, it is also not the time to fully commit resources to the upcoming season. Ainge saved the pieces for some moves this summer, not the total assault. Not unless LeBron James signs. Then you can trade for Kevin Love.

No, instead, it is time for the asset consolidation. It is once again time to do what Ainge has long loved doing the most; have that cake and eat it.

Washington Wizards v Boston Celtics - Game Seven

In signing one star or near-star and drafting another potential one, they will set themselves up for both now and the future. The youth movement sustains to some degree in all foreseeable Celtics offseason outcomes, and the fact that it does means that while the use-them-or-lose-them nature of their 2017 assets and current success level necessitate targeted immediate improvements this summer, the long game is still on.

Starting next season with a rotation featuring something like Isaiah Thomas, Avery Bradley, Jae Crowder, Gordon Hayward, Al Horford, Marcus Smart, Markelle Fultz, Kelly Olynyk and Jaylen Brown is a success of an offseason, certainly. And as we have seen above, it is a realistic one. In that scenario, Ainge gets what he wants. The Celtics get better, both sooner and later, and will have plenty of internal growth from the youth movement to pair with the Nets’s 2018 pick. That time does not win the title either. But it is a step or two closer to doing so than the current one.

While his value is potentially as high as it will ever be right now, the Isaiah question can be addressed later. Due to his defensive flaws, his impending free agency, the options immediately available with this summer’s assets and the need to balance the team, Thomas should be considered available in the right deal. Not for more draft assets, but someone comparable in talent whose skill set is more conducive to the Celtics’ balance post-July.

That may never happen. And that’s OK. You absolutely can win with Isaiah Thomas as a lead guard. You just cannot do so while also relying on career nights from Kelly Olynyk in decisive game sevens all that often. The 2016/17 Celtics had to do that once in a way that the 2017/18 and beyond Celtics will not have to. The strategy for the now is much the same as the strategy of the past, with just a slight amount more urgency.

But unless Kawhi Leonard, Giannis Antetokounmpo or Anthony Davis somehow became available, don’t go all in. Don’t forego the future for the short term benefits. Leave that sort of thing to the Pistons.

Washington Wizards v Boston Celtics - Game Two

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