There are a myriad of questions the Boston Celtics need to answer this summer. Some more important than others, obviously. By extending GM Danny Ainge and head coach Brad Stevens contracts, the owners have already answered the most important one: The Celtics will stay on course for the foreseeable future. As chairman Wyc Grousbeck said at the presser:

“We’re taking steps to just make sure this organization, as it moves forward, is completely in tune and rock solid as we prepare to really build this thing,” said Grousbeck. “We want to be contenders.”

And it’s in this light that the questions need to be asked and answered. Just as in 2007, before their last championship run, the Celtics have the assets and flexibility for anything between slight tinkering with the roster, to a complete makeover. Zero bad contracts, loads of future picks, and possibly enough room under the salary cap to sign two mid-level max contracts.

1. What should the Celtics do with the third pick?

This draft is a two horse race between Ben Simmons and Brandon Ingram. After those two, things get murky. Even players with serious red flags have been mentioned as possible top three picks. Right now, the consensus seems to be that Croatian 7-footer Dragan Bender is the top talent, but Kentucky freshman Jamal Murray might be right there with him.

But it’s not really about who the Celtics pick at no. 3, it’s whether they keep the pick or not. There might be a franchise player in the draft, but not one who will change what the Celtics are doing or where they’re going, at least for now. Not even Simmons, with his unique skill set, changes that (unlike for most other teams), since he could slide into the current rotation as Evan Turner’s replacement as a playmaker for the second unit. The real change comes if the Celtics find a trade for a star player before or after the draft.

This is the context you need to remember when you see rumors that the Celtics are shopping the no. 3 pick hard. They actually aren’t. They are pursuing any deal that can bring them a star player, and the no. 3 pick is the starting point in most of those deals. But it’s about getting a true star player, not about trading away the pick to avoid more young players. The Celtics already have two years of playoff experience with the current core, and a handful of players who might be ready to take another step up in Kelly Olynyk and Marcus Smart–who both need to play at a constant high level–and rookies Terry Rozier and Jordan Mickey, who should be ready for rotation minutes.

And Ainge has definitely put the Celtics in an excellent position to make trades this summer. Among his assets are three unguaranteed contracts worth close to $18 million dollars which can all be waived for free until July 3. The Celtics GM has also plenty of rookie scale players to match most salaries, plus the Celtics have cap room galore. So making a deal won’t be too difficult, while finding the right one might prove to be a challenge. The question is what the Celtics should be looking for other than star power.

A persisting rumor is that the Celtics might use the pick to trade for Philadelphia’s Jahlil Okafor, who comes off a slightly disappointing rookie season, which makes him a buy-low target. A trade like this could be interpreted in two ways: Either the Celtics still see Okafor as a possible franchise cornerstone (as he was seen by many people before his lone college season), or they simply see him as having a higher value than anyone they could pick in this draft. According to another rumor, it’s Neriens Noel who the Celtics are eyeing on the 76ers roster, which goes to show that you never really know with Danny Ainge until he has made his move.

The third pick is only the beginning of a long draft night for the Celtics, who have three first round picks and five second round picks. But going over which picks should be traded, which players will be stashed away overseas, and so on is a way too big a mouthful to chew on here.

2. Should they stay or should they go? (Celtics own free agents)

The list of possible free agents on Bostons roster:

Evan Turner

Jared Sullinger (RFA)

Tyler Zeller (RFA)

Jonas Jerebko (unguaranteed 2016-2017)

Amir Johnson (unguaranteed 2016-2017)

John Holland (unguaranteed 2016-2018)

This amounts to half of the regular rotation (plus Holland), but none of them seem “untouchable,” which says a lot about the current roster.

Sullinger was considered a steal in the 2012 draft at no. 21, and his first two seasons were very promising even though he had to get back surgery after his rookie season. He has shown elite rebounding skills and should probably have been the favorite to stay based on talent alone. But after entering every season overweight, and even failing to meet his weight goals two years in a row, he might have overstayed his welcome.

He’s also failed to show enough progress from three-point range to turn him into a legitimate outside threat. In a system and NBA age that puts a premium on versatility, his lone elite skill is not enough to make him more than a role player; and possibly not enough to make the Celtics match a large offer.

Tyler Zeller might be easier to keep around. He will probably not command more money than any other decent backup center. He is young enough to still have upside, though he hasn’t shown the most important skill for a big man: The ability to anchor a defense.

He did his best work for the Celtics in the beginning of the 2014-2015 season coming off the bench but sharing a lot of floor time with Rajon Rondo. He has a nice shooting stroke and might be better suited for playing pick-and-pop on the perimeter. In 2014-2015 he hit 47.7 percent of his long twos (beyond 16 feet) which dipped to 37.7 percent in 2015-2016, possibly due to worse looks.

Evan Turner is one of the players who thrives due to his versatility. He might not have one single great skill, but his playmaking and defense are enough to make him a 6th Man of the Year candidate, and that is his current ceiling. He can create mismatches against most second units, and he’s not afraid of the moment at the end of games. If he started hitting his threes again, he would be a much more valuable player, with size, speed, and skill set to play three positions on both ends of the floor.

The problem for Turner and other versatile players without elite skills is that they’re all replaceable, so it doesn’t make sense to pay them big money. Not even if you need two or three players to replace them.

Turner feels at home and wanted in Boston, and that might be enough for him to take a small discount to stay. But his status could be hanging in the air while the rest of the roster settles, which could eventually push him to sign elsewhere. The Knicks have been mentioned as a destination.

“The Swedish swish” Jonas Jerebko is probably the most underrated player on the roster. At 6-foot-10 he is very close to the ideal stretch four, hitting around 40 percent of his shots behind the arc while playing for Boston and a decent 19.9 percent in defensive rebounding (well below Sullinger, but slightly better than Amir Johnson).

Defensively, he can hold his own against most forwards and is fast enough to switch onto guards in the pick and roll. When he is on the floor with other flexible players like Crowder, Smart, Turner, and Bradley, the Celtics defense is at it’s most suffocating.

Jerebko’s biggest problem might be the way the roster is constructed currently. His best fit is in the starting lineup, replacing Jared Sullinger as he did in the last four games of the series vs the Atlanta Hawks. But is he better suited than Kelly Olynyk, who shoots just as well from three-point range and adds unique playmaking skills for a big man? Olynyk might still have a higher ceiling to add. On the other hand, Jerebko might have been underused. He has barely been used as the center in small ball (he played in one Boston lineup for 22 minutes in 2014-2015 and then again for 22 minutes in the Atlanta series), but he has a very good skillset for that.

Of all the decisions to make this summer, keeping Jerebko could very well also be the most underrated. And at only $5 million for next season, the only reason to drop him would be to acquire a second max contract player. In which case the discussion is probably moot anyway.

Amir Johnson is probably the “most likely to be traded” player. He’s on a very good unguaranteed contract, and while he is the most consistent among the Celtics big men, both his production and his intangibles seem very replaceable. A player like Al Horford can do everything Johnson can, only better. Some of it, like stretching the floor, a lot better.

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3. Will the stars align again?

The Celtics waited several years before the right opportunity arrived in the summer of 2007, when they acquired Kevin Garnett and Ray Allen. And while in 2014 Wyc Grousbeck spoke of possible “fireworks” that summer, it’s clear that Danny Ainge doesn’t jump on just anything. The situation now is very comparable to nine years ago, except the Celtics are much further ahead in a rebuild, and even after this summer they will have a load of assets on their hand.

The obvious question is who the Celtics can add either in free agency or through trade.

The pipe dream free agent is Kevin Durant. But even if Durant might consider leaving Oklahoma at some point, it seems unwise to do it this summer, both from a monetary standpoint and a basketball one. A rumor says that the Celtics have a “wish list” from Durant regarding players that he wants on the roster. If that is true, it adds an interesting twist to everything the Celtics do this summer.

Other free agents that the Celtics will reach out to: LeBron James (courtesy call), Hassan Whiteside, Al Horford, Andre Drummond (RFA), DeMar DeRozan, Dwight Howard, Bradley Beal (RFA), Harrison Barnes (RFA), Chandler Parsons, Nicolas Batum, Bismack Biyombo.

The key words are: Rim protection, (efficient) volume scoring and versatility. It should be possible for the Celtics to acquire at least one of the above players, even if close to every team in the league will have money to burn in free agency.

But even getting, say either Howard or Horford and Batum, is hardly enough to push the Celtics into contender status. They might actually hurt their chances by committing to a second tier core.

Even if the Celtics succeed in forming the best defensive team in the league, every successful playoff team has a potential top 10 offensive player or more on the roster. Only Durant (and James) fits that bill among the free agents. Even though Whiteside and Drummond are very effective, they fail by not scoring in high enough volume. Drummond could gain a great deal by rule changes to prevent hack-a-player tactics, though.

Anyway, the Celtics will need to trade some assets in, and the rumor list will be endless. The main targets should be players like DeMarcus Cousins, Paul George, Jimmy Butler, Kevin Love, and maybe even Blake Griffin, Carmelo Anthony, or Marc Gasol.

None of the above-mentioned players are actively being shopped, but they’re also not untouchable in their current situation (or at least they might become available under the right circumstances). So obviously Danny Ainge is the active one on the phones. And that’s probably how the rumors that the Celtics are shopping their top pick started.

Behind this group of players with proven star power, Ainge probably has a list of players who like Isaiah Thomas can shine under the right circumstances or who are rising stars. Utah’s Gordon Hayward, with his Butler connection to coach Stevens, has been mentioned in rumors, as well as Milwaukee’s Jabari Parker and Khris Middleton.

4. Possible ways to consolidate without giving up flexibility?

The Celtics need to have a whole set of contingency plans in place with all the draft picks this year in mind. With the roster limit at 15, they will need to either trade away picks/players or stash players overseas.

How valuable are the Celtics picks? The no. 3 pick might not be as highly valued as in other years, but no. 16 and 23 could very well yield rotation players or some very interesting boom or bust prospects.

The twist here is that four teams (Sixers, Celtics, Nuggets, and Suns) own 11 of the first round picks, which means that we have seven teams without a pick in the first round. Even more teams are without 2nd round picks. So unlike many other seasons, this is potentially a seller’s market.

And while the cap situation makes it possible to hire more veterans, rookie scale players should still come with a premium if only because of their possible upside.

Trading their picks one-by-one is obviously not the Celtics’ first choice. So if they start doing that on draft night, it should be a sign that they have switched to plan B in order to save assets.

5. After all, what’s the worst thing that can happen?

The core of the team consists of three players, Isaiah Thomas, Avery Bradley, and Jae Crowder. You could argue that Marcus Smart belongs there too, but he hasn’t arrived yet.

Thomas, Bradley, and Crowder are young veterans on insanely cheap contracts. They’re locked up for less than $22 million a yearr until 2018. That’s three players who could plug-and-play on any team in this league: a scoring All-Star point guard, a three-and-D All-Defensive First Team shooting guard, and a versatile forward who plays elite defense for his position.

Consider that even with these three players, plus Smart, Kelly Olynyk and Terry Rozier (plus others) on their rookie deals next season, the Celtics still have cap room for two max contracts (only the 30 percent versions though). Only the two teams from the bottom of the league, the Philadelphia 76ers and the Los Angeles Lakers, and the Dallas Mavericks (dependent on players terminating their contracts) have more cap room.

Thomas, Bradley and Crowder are not only the main cogs in the Celtics machine room. They’re also the key to the team’s financial flexibility. Just like it was key for the San Antonio Spurs to have Duncan at a huge discount ($6 million) in order to get LaMarcus Aldridge on the team last summer.

That brings us to the worst case for the Celtics this summer, which starts with Danny Ainge getting a sunstroke and go on a parade of bad decisions:

- Overpaying for Okafor, Butler, Love and/or other players who aren’t guaranteed to add star power.

- Adding bad chemistry to the roster. (“Hello Mr. Cousins, please leave the drama somewhere outside the building.”)

- Losing draft picks for nothing of value (that includes picking busts in the 1st round).

- Giving up flexibility for a small improvement without adding star power.

In short: Ainge really has to screw things up big time before the Celtics lose their long-term competitiveness. They might not be ready to challenge the top next season, but they should get closer, whatever happens this summer.

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