Philadelphia 76ers enter offseason at a critical crossroads

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And so the most fascinating offseason in the NBA begins.

The Philadelphia 76ers lost Game 7 in Toronto in heartbreaking fashion, falling in the Eastern Conference semifinals for the second straight season, this time by the hand of Kawhi Leonard. With 4.2 seconds left, after evading Ben Simmons and Joel Embiid, Leonard hit a fall-away go-ahead jumper from the corner that brought tears to Embiid’s eyes and the Sixers’ season to an abrupt close.

Embiid was emotional for good reason. The Sixers put up a much better fight in this series compared to their five-game loss to the Boston Celtics last year. These Raptors are a much stronger team than last year’s Celtics, and still, Philly extended it to the very last possible second.

It’s a cold, harsh ending that perhaps only the steely Leonard could bring. And now, the next chapter begins. With seven of the Sixers’ top nine players able to be free agents this summer, including Jimmy Butler, Tobias Harris and JJ Redick, this figures to be an explosive summer in the City of Brotherly Love.

Let’s go through the three big questions surrounding this franchise.

1. What happens to Brett Brown?

By NBA coaching standards, Brett Brown is an elder statesman. Only six coaches have longer tenures with their team than the Sixers’ coach. Among them, Gregg Popovich, Erik Spoelstra and Rick Carlisle have won championships with their their respective clubs; they’ll coach their teams as long as they please. Terry Stotts, Brad Stevens and Doc Rivers are the others, and they have only missed the playoffs once each in their six-plus years with their clubs.

And then there’s Brown, who hasn’t had nearly the same success as the six ahead of him. Part of that was by design. Hired by a different decision-maker than the current one to oversee one of the biggest teardowns in NBA history, Brown accelerated the playoff timeline by getting the Sixers to the playoffs in Simmons’ rookie season in 2017-18. But even still, Brown might be the first domino to fall after the Game 7 loss to the Raptors, a team that also shouldered enormous expectations going into these playoffs.

It’d be extremely hasty to evaluate Brown’s capabilities over one Game 7, but there’s been plenty of smoke surrounding Brown’s position and no one has extinguished it. Owner Josh Harris, speaking at the MIT Sloan Conference in early March, made headlines by saying it’d be “very problematic” if the Sixers lost to Boston in the opening round of the playoffs. He later told ESPN, “we have enough talent on our roster that if we play the way we’re capable of playing, we can beat any team in the East.”

It’s not hard to read between the lines there. Brown’s job security seemed even more tenuous after Harris and general manager Elton Brand held an impromptu press conference before Game 1 of the first-round matchup against the Brooklyn Nets. Harris wouldn’t commit to Brown beyond the season in that surprise session. When asked if Brown would keep his job no matter the outcome of the playoffs, Harris credited Brown for “a tremendous job” after two 50-win seasons and then later summed it up by saying, “right now, we’re supportive of Brett.”

Executives around the league have been surprised by the lack of external support Brown has received from the organization -- most alarming is Brand’s silence on the matter. Said one long-time executive: “Elton could have killed all that talk and hasn’t.”

It’s reasonable to wonder if Brand has that kind of power at all. It took the Sixers three months to decide that Brand was the right replacement for Bryan Colangelo after his resignation in June 2018 amid a social media scandal. Brand had just been named the vice president of basketball operations and ran the G League affiliate Delaware Blue Coats before being hired to run the big-league club.

Brand was chosen, in part, because he would be a collaborative decision-maker whose relative inexperience (he was playing for Brown in 2015-16) would lead to stronger partnerships in the organization. In other words, Brand wouldn’t have full autonomy. League sources have long suspected that if Harris feels disappointed this postseason, organizational changes may be in order, going deeper than just the head coach.

It’s been a confusing power structure ever since Colangelo stepped down. Remember, it was Brown who was the interim GM in Colangelo’s place and was heavily involved in the hiring process that led to Brand becoming the full-time leader. Some around the league saw it as a cost-effective placeholder move that would be, as one executive described it, “easier if you have to do a total reset.” From that perspective, the question is not whether Brown is let go, but if Brand’s job may be in jeopardy, too.

Said one source with knowledge of the situation: “I think there’s a chance it’s wholesale changes top to bottom. It’s a strange situation.”

In that pre-playoff press conference, Harris did call for Brand to be voted as the NBA’s Executive of the Year, which is notable considering the non-committal he gave for Brown.

But the real question is whether Brown is the right person for the job. Yes, the Sixers didn’t make the Eastern Conference Finals, but it’s hard to blame Brown for that unless you want to accuse him of infecting Embiid with multiple illnesses. Really, Embiid’s gastroenteritis and upper respiratory issues, which clearly limited him and his minutes in this series, are what separates the Sixers from this exit and reaching the conference finals. The Sixers were plus-90 in the 237 minutes with Embiid on the floor this series and minus-109 in the 99 minutes he sat.

Against Brooklyn, maybe the Sixers survive their best player getting what amounts to the flu. But Leonard and the Raptors are too good to not capitalize on Embiid needing overnight IVs. The Sixers were expected to improve the depth of the roster with buyout candidates, but the front office didn’t land any significant pieces this season like it had with Marco Belinelli and Ersan Ilyasova in ’17-18.

Though Brown wasn’t handpicked by this front office, he deserves another shot next season. The Sixers remade the roster twice midseason on the fly. The starting lineup -- without a preseason or training camp -- ended up being the most effective starting five outside of Golden State. Maybe the organization determines he’s not the right person to lead the next phase. But give any coach the cards he was dealt, and I’m not sure they do any better.

Even if Harris believes Brown did a fine job, he may want a different voice than Brown to lead the team in this next chapter. Toronto did that last year, and look at where it got them. Like Dwane Casey, Brown wouldn’t be without a job long if that’s the direction Philly goes.

2. Will Jimmy Butler and/or Tobias Harris be back?

Though Josh Harris hasn’t extended a strong vote of confidence toward Brown, the owner has made it clear: He wants Jimmy Butler and Tobias Harris back. At every turn, he’s all but said he will offer max contracts to both of them.

Harris will be an unrestricted free agent and figures to be a max guy in this seller’s market. Sources around the league expect Brooklyn, Dallas and New York to be in line for his services if he decides he wants out of Philadelphia. Like Butler, Harris is eligible to sign a five-year, $190 million contract with the team. Outside suitors can only offer him, and Butler, a four-year contract for less annual money.

It’ll be costly, especially in 2020-21 when Simmons’ expected max-level extension kicks in. Keeping Butler, Simmons, Harris and Embiid will cost about $130 million that season, when the salary cap is projected to be at $118 million. That’s the cost of keeping four All-Star players in their prime.

Butler, who will be 30 years old next training camp,  won’t be in his prime for long. How quickly he ages will determine how prudent offering a max contract will look. But right now, he deserves it. Depending on who you ask around the league, Butler is a top 10-to-20 player in today’s NBA, excelling on both ends of the floor. ESPN’s real plus-minus metric placed Butler as the 18th-most impactful player in the league this season and one of just three wing players who registered at least 2.0 RPM rating on offensive and defense (Paul George and Pascal Siakam were the others).

Butler didn’t pick his trade destination and may have his sights set on brighter stages in Los Angeles and New York. But Philadelphia offers him a chance to be, as Brown reminds every other game, “the adult in the room” while not having to play 40 minutes a night. He can age gracefully next to Simmons and Embiid rather than having to play the alpha gunner role that can grind a body to a pulp. It’s not my money, but I’d be confident in paying up for the Philly Phive going forward.

Yes, there’s considerable risk in giving Butler a five-year max. He has played more than 67 games in just two of his eight seasons in the NBA. Those seasons have been riddled by injuries that may or may not be related to the fact that no player has averaged more minutes per game than Butler since he became a full-time starter in Chicago in 2013-14. That’s a lot of mileage on those tires.

But the Sixers have taken matters into their own hands, slicing his minutes down to 33.4 minutes per game, considerably lower than it was in Minnesota before the trade (36.1) and last season (36.7). The Sixers are certainly not playing him like a rental. They have the long-term in mind. With Chris Paul, John Wall, Gordon Hayward and Blake Griffin all making more than $30 million in each of the next two seasons, Butler’s contract would hardly be untradeable if he drops off.

As for Harris, it’s a myth that max players have to be No. 1 options on a championship-caliber team. What is true is that every championship team needs three or four max guys on its roster. Harris’ skill set as a big pick-and-roll scorer and an elite shooter is befitting of that role, even if his percentages dipped in the short 39-game stint with Philly. He’s better than he showed in the playoffs. At 26 years old, Harris has improved his scoring average in each of the last four seasons and still has room for improvement.

If the starting five hadn’t been so successful this season, I’d save the money and move on. But with it already being a top five-man unit despite Simmons’ age and no training camp, it’s worth paying well into the luxury tax.

3. Is Ben Simmons still a franchise pillar?

Simmons is one of the best young players in the NBA. He’s an All-Star at 22 years old, capable of one day being the NBA Defensive Player of the Year and already a nightly triple-double threat.

It’s also true that he took zero shots outside of 12 feet this entire postseason, per Basketball-Reference. He took eight such shots last postseason. It’s not that he doesn’t have a reliable jump shot. It’s so raw that he hasn’t had the confidence to even try on the playoff stage.

For some league executives across in the NBA, this is not just a flaw in his game; it’s a sign that he isn’t serious about improvement. This was the one thing that he had to work on this past summer, the one skill he lacked in the sport. How can someone be so talented and yet so limited in this vital area of the game?

Well, he’s 22 years old and already one of the best players in the game. Fair or not, Simmons failing to add some semblance of a jump shot in Year 2 of his career is seen as a reason that Philadelphia has to put him on the trade block. Perhaps this is just wishful thinking by rival executives. There has been no indication from the Philly side that Simmons is being floated or will be this summer.

It’s early in that process. Leonard’s shot just fell through the net. But one Western Conference executive brought up a name that could be a Simmons trade target: LeBron James.

“I think they very well might explore that,” said a rival executive of Philadelphia.

James doesn’t have a no-trade clause, but he shares the same Klutch Sports agent with Ben Simmons in Rich Paul. James has two seasons left on his deal before he can become a free agent. After a disastrous offseason in which their president of basketball operations abruptly resigned and they struck out on their top two head coaching targets in Monty Williams and Tyronn Lue, do the Los Angeles Lakers honestly believe they can put together a championship contender in the next two seasons?

If the answer is no, trading James has to be on the table. And if you’re going to do that, there’s a short list of players that would be worthy of being traded for the King. Simmons is certainly good enough to be on it.

A Simmons-James swap becomes tricky because Simmons makes $8.1 million next season, before his rookie extension kicks in beginning in 2020-21 (he will be eligible for extension this summer). Because of that comparatively low salary, Simmons will have to be packaged with another max-level player, or near it, to match James’ huge $37.1 million salary for 2020-21. The Sixers could ink Harris to a sign-and-trade, but not for the five-year max. The new collective bargaining agreement removed that option from the toolkit. Harris would only agree to that if the Lakers were over the cap, which they’re not currently, and Harris desperately wanted to go there. The same goes for Butler in a potential blockbuster trade. Again, this is tricky.

There’s another wrinkle to this: Ty Lue turned down the Lakers job for a reason. He felt he could get a better job elsewhere. He’s holding out for something. Could that job be Philly? It’s not available at the moment. But there’s more than just a little chatter about the Sixers and the Lakers being potential trade partners this summer. Crazier things have happened in this league than Lue and James on a Sixers sideline next to Embiid.

Several executives see a major shakeup in Philadelphia this summer. Harris has already signed off on two blockbuster moves in the past seven months and a third blockbuster if you count trading former No. 1 overall pick Markelle Fultz. Is another on the way? Many around the league believe so. Said one long-time executive: “Harris won’t be able to resist.”

The safe money is that the Sixers brings the Philadelphia Phive back for redemption. The opinion here is that Simmons is too good and too young to bail on now. We just saw Portland break into the Western Conference Finals with their same core after two humiliating postseasons.

But then again, Toronto traded their beloved star in DeMar DeRozan this past summer and look where it got them. Which way will Philly go? There may be no bigger question in the NBA this summer.

Follow me on Twitter (@TomHaberstroh) and bookmark NBCSports.com/Haberstroh for my latest stories, videos and podcasts.

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