Meet Sachin Gupta, The Driving Force Behind Many of Sam Hinkie’s Trades

The Sixers rebuild was the result of a collective team effort. Included in that group is Sachin Gupta, the architect behind the trade with the Sacramento Kings.

Left: Joel Embiid (Cal Sport Media/Associated Press); right: Ben Simmons (Steven Freeman/NBAE/Getty Images)

Joel Embiid (Cal Sport Media/Associated Press) and Ben Simmons (Steven Freeman/NBAE/Getty Images) were acquired as a result of the Sixers’ rebuild. Was it worth it?

The Philadelphia 76ers — winners of 11 of their last 16 games, sitting just 4.5 games of the playoffs, and, most importantly, led by the kind of generational superstar that promises to make them relevant for the foreseeable future — have started to capture the imagination of the Philadelphia sports fan in a way almost nobody could have predicted just a few short months ago.

Almost nobody.

Much of that excitement is predictably centered around Joel Embiid, the third-year rookie taking the NBA by storm. Embiid is averaging 20.2 points, 7.8 rebounds, 2.1 assists, and 2.5 blocked shots per game, despite having his playing time limited to just 25.4 per contest as he works his way back from two missed seasons because of an injury to the navicular bone in his right foot. Despite the limited playing time Embiid has showcased the diversity of skills that could, perhaps should, make him one of the best two-way players of his generation.

For many fans that right there would make the last three years worth it. Yet if Embiid is the surface layer of the Sixers’ puzzle, the most obvious and readily available reason for excitement around the trajectory of the rebuild, there are many different layers beyond Embiid that could prove to be special in just a few years’ time as well.

The most obvious of that is Ben Simmons, the Australian phenom drafted #1 overall last June who should be making his NBA debut in just about a month’s time, providing that elusive second prospect to take this rebuild to yet another level.

Beyond that are a series of moves which give the Sixers tremendous flexibility going forward.

In former general manager Sam Hinkie‘s resignation letter he talked about a zugzwang, a chess term which describes a situation where a player’s future is compromised by any move left on the board, where any decision will weaken the strength of their position going forward.

As the Sixers stand here, 4.5 games out of a playoff spot that nobody expected them to challenge for, featuring a generational talent that many doubted would ever take the court, they find themselves in the opposite situation: any outcome should move the rebuild forward in a meaningful, exciting way.

If the playoff push — which still seems unlikely, but also seems less and less absurd by the passing day — falls short the Sixers will end up with a lottery pick in a deep draft, along with extra ping pong ball combinations thanks to the right to swap picks with the Sacramento Kings, the chance to get yet another lottery pick from the flailing Los Angeles Lakers, the experience of playing meaningful games late in the season, and the confidence created because that unexpected playoff race was ignited by the faster than expected coming-of-age story of one of the game’s truly elite talents.

If the playoff push succeeds the Sixers gain invaluable experience and a boost in prestige, using the allure of joining Joel Embiid and a playoff run as marketing chips in free agency, where oh-by-the-way they’ll have as much money to spend as anybody thanks to a cleaning of the books under the former administration.

They’ll also still have the possibility of ending the day with two top-10 picks in June’s draft, an incredible situation to be in for a team on the rise, decoupling their ability to acquire elite young talent away from the natural ascension the team will see when a dominating force like Embiid finds his footing.

Even the worst case scenario, such as the Lakers ending up with a top-3 pick after May 16th’s lottery, causing them to retain their pick for yet another season, looks wildly optimistic. The Sixers would still end up with a likely top-10 pick in the 2017 draft (either their own or the Kings, whichever is better), then unprotected picks from the Lakers in 2018 and the Kings in 2019, teams that have lost a combined 291 games over the past three years and face seemingly constant turmoil.

That scenario, with an unprotected Lakers pick in 2018 and an unprotected Kings pick in 2019, is considered by many to be the *worst case scenario*, what happens if every chance occurrence goes against the Sixers’ favor. Think about that for a second.

It’s the kind of situation that doesn’t happen without the meticulous planning of a select few.

The most obvious architect behind the Sixers rebuild is Hinkie, and he certainly deserves a lot of the attention, good or bad, for where the Sixers are and how they arrived at this juncture.

But like most well-functioning teams those decisions were made by a great many, and the Sixers’ previous regime was no different. One such architect was Sachin Gupta, Hinkie’s second in command, who left his position of Vice President of Basketball Operations last summer.

* * * *

Gupta and Hinkie first came to know each other while working for the Houston Rockets, originally working side by side in cubicles as the Rockets underwent a controversial front office transformation of their own.

Daryl Morey first met Gupta when Morey, then the Senior Vice President of Operations with the Boston Celtics, gave a guest lecture at an alumni gathering for MIT students.

Gupta, a recent computer science and electrical engineering graduate of MIT who was working as a software engineer for ESPN at the time, stuck around when the talk was over to chat with Morey one-on-one.

Morey, of course, met with many young adults looking to enter the sports world, a hypercompetitive industry with depressingly low odds to break into. But Gupta left an impression on Morey because of how proactive he was, even as a relative outsider, in pushing the boundaries of statistical analysis. The fact that Gupta had proven his coding ability as an engineer at ESPN made him even more desirable.

Gupta left the talk blown away, but not really sure the extent to which the interest was mutual. Still, he knew he wanted his future to be in basketball and he kept in regular contact with Houston’s future general manager.

When Morey was hired by Houston just a little over a year later, Gupta immediately applied for one of the numerous positions Morey posted to fill out his staff. His role with the Rockets was one that started off in a more traditional, technical variety, building the databases and generating the reports that Morey and VP of Basketball Operations Sam Hinkie would use to help them make decisions.

But while Gupta’s connection to Morey may have helped him get his foot in the door, he was also fortunate enough to work in an environment that was built on meritocracy. Emboldened by the open environment Morey and Hinkie created, Gupta, who became an expert on the ins and outs of the NBA’s Collective Bargaining Agreement while developing the trade machine at ESPN, began branching out, pitching trade ideas to Morey and Hinkie despite not having the job title most would deem necessary to be taken seriously.

One such instance was the buildup to the summer of 2010, the year of LeBron, when every team in the league was clearing cap space, convincing themselves that they had a real chance to sign James and turn their franchise around. The Rockets took the the road less traveled, using their cap space to capitalize on the rest of the league’s unrealistic optimism in order to gain additional youth and draft picks, such as Jordan Hill, a future 1st round draft pick, and the right to swap first round picks with the Knicks, pieces which would prove valuable as the team tried to rebound from the devastating injuries to Yao Ming and Tracy McGrady.

That trade, according to those involved with the Houston front office at the time, was the brainchild of Gupta. Over the years this would prove to be Gupta’s forte, even more so than the comfort level with statistics that got him in the door.

“I give all the credit in the world to Daryl [Morey] and Sam [Hinkie] for allowing me to grow in this path,” Gupta told Philadephia magazine recently. “Sam tried as hard as he could to create a true meritocracy. Your responsibilities and your voice grow with the work that you put in.”

Gupta thrived in this environment, with his voice, and role, growing as he proved his worth. He would eventually leave the Rockets to pursue an MBA from Stanford University’s Graduate School of Business, although that time away from the game proved to be brief as Gupta was immediately brought in to be Hinkie’s #2 when the Sixers hired the now-controversial executive away from the Rockets in the spring of 2013. The Rockets, according to sources, were going to try to bring Gupta back once he was finished with his MBA, but his familiarity with Hinkie and the chance to be the #2 man in Philadelphia would make the decision easy.

Gupta would eventually finish the degree while doing double duty with the Sixers.

* * * *

It’s not really all that surprising, considering his background in computer science, that Gupta’s role with the Sixers would be characterized by most as being an “analytics guy”, a marginalization rarely done for a team’s second in command. Truth be told Gupta’s role with the Sixers rarely involved hands-on work manipulating code or databases, graduating to become a stakeholder of such systems rather than the architect.

Analytics, as a field, is frequently simplified down to formulas and rankings, databases and projections. Certainly that is all part of the process, and something built during Gupta’s time with both Houston and Philadelphia. You would be hard-pressed to find a team that isn’t investing in these resources at this stage of the game, and usually with incredibly bright, well-educated individuals to fill out the staff.

But more important than Gupta’s ability to design a database or tweak a formula, more important than Bayes’ theorem or the verdict of a Brier score, was the mindset he brought with him, an application of the scientific process to a field that is still too often controlled by gut instinct. The transition, Nobel Prize winning economist Daniel Kahneman might say, from thinking fast to thinking slow.

The life of a basketball executive is a rather unique field, one in which decisions are, by and large, made upwards of three times per year. In some fields, especially ones which require split-second decision making, a mostly correct decision made on time is more valuable than a correct decision made late, and we develop mental shortcuts in order to make these decisions in the blink of an eye. These shortcuts can lead to biases, biases which can then lead to mistakes, a phenomenon Gupta is keenly aware of. Gupta kept a poster of 20 common biases at his desk, a constant reminder of pitfalls to watch out for. He played the role of social scientist in addition to that of statistician and salary cap expert.

In fact, the more you talk to former members of the Sixers’ front office the more they come across like something else entirely: forecasters. Spend some time with Gupta and the Sixers’ former brain trust and you come away thinking these guys would be right at home in Philip Tetlock‘s Good Judgment Project, right down to a focus on empiricism and an avoidance of absolute answers.

(*Side note: The popular website, FiveThirtyEight, uses a fox for its logo, a reference to the famous phrase by Archilochus that “The fox knows many things, the hedgehog one big thing”. This has been adopted as a popular dichotomy for forecasting, made popular by philosopher Isaiah Berlin, and discussed extensively by Tetlock).

One of the frequent criticisms of Sam Hinkie’s front office was its lack of traditional “basketball guys” at the top, as none of Hinkie, Gupta, or Ben Falk (VP of Basketball Strategy) played high level basketball. To say that was intentional may be overstating the situation, but it certainly wasn’t something Hinkie seemed to shy away from, either, looking to build the best staff of decision makers he could, not just the smartest collection of basketball minds who happened to have the genetics required to physically compete at an NBA level.

For whatever obstacles their backgrounds presented it also provided them with benefits as well, including an increased tolerance of risk and a unique perspective on making decisions.

Many in this industry have been around the game their entire life, with backgrounds that have so far diverged from other industries that life outside of the game seems entirely foreign. That difference between a desire to be involved with the game you’re passionate about, compared to a need to fill one of a finite number of positions, can be a fine line to walk, and one that can alter the way risk is approached. If you could pick just one driving force behind crippling long-term mistakes, self-preservation, and the impatience that comes along with that, would likely win in a landslide.

For Hinkie’s front office this was a competitive advantage to exploit, a unique outlook on running a team not frequently found in today’s reactionary sports culture.

The good news for Sixers fans is that, while it may have taken some time, many of the forecasts that Hinkie, Gupta, and crew made now appear to be coming to life.

* * * *

The most obvious decisions that are now paying off came during the 2014 draft, with the selection of Joel Embiid with the 3rd overall pick and the trade to acquire the rights to Dario Saric, drafted 12th overall and, at the time of the 2014 draft, under contract for the next two seasons with the Turkish club Anadolu Efes.

Those decisions were controversial at the time because neither would contribute immediately. Embiid’s medical red flags, which included a stress fracture in his back and a fracture in the navicular bone of his right foot, scared off many general managers and prognosticators alike. Saric’s lack of immediate availability meant he was less valuable to most. Not the Sixers, however, who bet on long-term talent over immediate reward, and Embiid and Saric are now first and second among all rookies in scoring this season.

Beyond that what has become obvious is that many of the other moves that have put the Sixers in this enviable position — that inverse zugzwang, if you will — were forecasts that turned out to be true.

Michael Carter-Wliiams, fresh off a Rookie of the Year season, was traded at the 2015 trade deadline, a move criticized by many because they traded a “known” commodity (whatever that actually means) for an unknown future reward, highlighting a key fundamental difference in thought process. Teams, more often than not, are unrealistic about the actual value of their players, especially young players, and turn down countless offers that may never become available later on down the line.

Two years later and Carter-Williams, traded for Tony Snell earlier this season, has bounced around the league, oscillating between DNP-CD’s and desperate promotions to the starting lineup on one of the league’s more dysfunctional teams. The Lakers, meanwhile, have remained bad, somehow avoiding the rapid ascent many incorrectly predicted for one of the NBA’s more storied franchises.

Perhaps no trade exemplifies an organizational philosophy, and creativity in using their unique cap situation to their advantage to “create luck”, better than the trade with the Sacramento Kings. The trade brought in Nik Stauskas, Carl Landry, Jason Thompson, the right to swap draft picks (at the Sixers’ discretion) in both the 2016 and 2017 drafts, as well as a future draft pick from the Sacramento Kings, which will now end up conveying as an unprotected pick in 2019. The going rate? The 47th and 60th picks in the 2015 draft and the ability to adsorb the contracts of Stauskas, Landry, and Thompson.

The right to swap picks with the Kings was viewed by many, perhaps even the Kings themselves, to be worthless, a window dressing addition to the trade that was never going to materialize. The outside view thought there was no chance for the Kings to be worse than the Sixers, who at the time were about to embark on an almost historically bad season. So what’s the point?

(Let’s ignore, for now, the free lottery ball combinations the Sixers received last year, bumping their odds at the #1 overall pick up from 25 percent to nearly 30, a hardly inconsequential consideration).

Yet here the Sixers are, unexpectedly tied with the Kings in the loss column after last night’s thrilling 122-119 victory, two teams seemingly headed down different paths. That worthless pick swap is now very much in play, an unprotected draft pick from a team that hasn’t made the playoffs in a decade sitting comfortably in their back pocket, all because the Kings were overconfident in their forecast over how much that little bit of cap space granted to them in the summer of 2015 would change the course of their franchise.

While characterized as an “analytics guy”, Gupta was more often than not at the forefront of trade activity with the Sixers, constantly brainstorming trade ideas and with an uncanny ability to look at the trade from the other side and correctly assess their motivations and ambitions, coupled with a deep understanding of the collective bargaining agreement and a creative mind. Depending on relationships with other team, time constraints, and schedule, Gupta would also, from time to time, conduct at least part of the negotiations himself.

In fact, according to multiple sources with knowledge of the Sixers’ front office proceedings, there wasn’t a trade of significance that Gupta didn’t have his hands in, an aspect of the Sixers’ rebuild even their most ardent detractors would almost universally admit was well executed. “His whole life revolved around that day in February,” one Sixers staffer told me, referring to February’s trade deadline. Those same sources describe Gupta as the driving force behind the Kings’ transaction, a trade which now looks to have set the Sixers up so enviably for the near- and long-term future.

The Sixers’ front office will frequently be characterized, dismissively so, and only from those on the outside, as “geniuses”. In truth the NBA is filled with a plethora of smart minds. If anything, the Sixers were looking for a fresh perspective to solve the age-old problem of team building in a zero-sum game.

It’s a problem teams all over the sports landscape are increasingly turning to an outside perspective to solve, to guys with the temperament and mindset to aggregate different perspectives, combining institutional knowledge of scouting departments, analytics departments, and the economic realities of the collective bargaining agreement to craft a clear team direction. Whether that’s Paul DePodesta with the Cleveland Browns or Theo Epstein with the Cubs, who rose from public relations assistant to destroyer of century-long curses in a staggeringly short period of time, teams are increasingly thinking outside the box for a fresh perspective.

* * * *

Since leaving the Sixers over the summer Gupta returned to his native Boston area, rediscovering a work/life balance that’s impossibly difficult to maintain in the world of front office executives. He’s remaining close to the Sixers’ ownership group, working as an adviser to their many sports franchises and business dealings. He’s also kept in contact with NBA circles, heading to various events, such as this month’s D-League showcase, the life of an NBA addict with every intention of getting back in the game.

Gupta continues to maintain an active interest in his former team from afar, a fixation which he admits can be difficult at times because of the way it ended and because of the promise they believed was still there, but buried under bad lottery variance and soul crushing MRI scans. Yet there’s a connection there, both with his work and with Embiid’s personal journey, that is far more personal in nature.

There’s also a truth that’s impossible to ignore, which is that the reputation of the architects of the Sixers’ rebuild is intrinsically linked to the progress the rebuild makes, even after they’ve left. It’s an odd twist of fate for a group that believes so passionately about process over results, that a chance occurrence in either direction doesn’t necessarily make a 60-40 projection wrong. Such is the rollercoaster journey in a field still largely judged through a deterministic lens.

While Hinkie, Gupta, Falk, and crew were still with the team a shockingly small number of their long-term gambits bore fruit, at least in the time frame they needed them to, no doubt influencing the narrative around what they were looking to do.

In just a short amount of time that equation has been flipped on its head, with Embiid returning to health, lottery ball combinations netting Ben Simmons in the draft, and future draft assets like the Lakers pick and the Kings pick swap coming into focus, looking increasingly likely to provide a spark to a rebuild already in high gear.

The Sixers have started to pass some of their rebuilding peers, teams like the Lakers, Suns, and Magic, in the standings, while holding the highest upside player of the group and having the most unplayed chips still sitting in their back pocket, waiting to be thrown into the middle of the table when the right opportunity presents itself.

That drastic change in course could cause everyone — fans, media, peers, league owners — to look at the previous regime in a drastically different light, even if they themselves might argue it shouldn’t change a thing.

Derek Bodner covers the 76ers for Philadelphia magazine. Follow @DerekBodnerNBA on Twitter.