What a Journey

August 29, 2018 GMT

Back in February of 2010, the Houston Rockets were at a crossroads, staring at an uncertain future with their roster.

Perennial All-Stars Yao Ming and Tracy McGrady, the franchise players that Houston had built around, were breaking down due to injury, and it had become abundantly clear the Rockets were not a true championship contender.

Billerica High graduate (class of 2000) Sachin Gupta had been brought into the Rockets’ front office years earlier by general manager Daryl Morey, in part, to solve problems like this. Like Morey, Gupta was a graduate of MIT and an analytics whiz who had a firm grasp on the NBA salary cap structure. After college, Gupta was hired by ESPN, where he invented ’s NBA Trade Machine, which has allowed countless basketball fans to fancy themselves as GM’s.


Gupta racked his brain to come up with a way to give the Rockets more flexibility and point them in the right direction. With the trade deadline looming, he finally had an epiphany one day in the shower.

“It just hit me,” recalled Gupta. “I didn’t love the idea of letting Tracy’s contract expire and play in free agency. Houston is a pretty big market, but every team in the league was trying to create space for that summer of free agency. Between New York, LA and Miami, I just didn’t love our chances of getting one of these marquee free agents. As far as trading Tracy for someone to help us now, I just felt that we weren’t really close enough that it would make that big of a difference. So I realized since everyone was so desperate to create cap space, we should play on that. New York, in particular, was really desperate to create double max-contract room and they had some interest in Tracy. So, the idea was to trade Tracy to them and take back a bad contract of theirs and extract as many assets as we could out of them.”

Morey loved Gupta’s idea and the Rockets executed the trade they were looking for. They agreed on a three-team deal with the Knicks and Sacramento Kings that sent McGrady to New York. The Rockets received Kevin Martin and Hilton Armstrong from the Kings and Jordan Hill and Jared Jeffries from the Knicks. Houston also got the right to swap first-round draft picks with New York in 2011 and received New York’s first-round pick in 2012 (top-five protected).

Morey has stated that Gupta’s contributions to the Rockets were invaluable. The 36-year-old former cross country and track runner at Billerica High has turned himself into a sought-after league executive.


In early August, Gupta was hired to be the assistant general manager of the Detroit Pistons after a six-year stint with the Rockets and a three-year run in the Philadelphia 76ers front office.

Ed Stefanski, a special advisor to Pistons owner Tom Gores, said Gupta has a great handle on analytics and will be a “tremendous resource” for the basketball operations team.

It’s been a remarkable path for someone who never played a season of high school basketball at Billerica.

“He was very intelligent, very empathetic. He was also inquisitive and focused. Just a great kid,” said Billerica High School Principal Tom Murphy, who taught Gupta in eighth grade history. “The nice part about Sachin is he was always a gifted math student. He loved math and he loved sports, too. He was able to take two things that he really loves and make a career out it. The level of humility that Sachin has is off the charts. If you talk to him, he acts like he’s never done anything.”

Gupta studied computer science and electrical engineering while at MIT. He was always an avid sports fan, especially of the NBA. He wanted to combine his degree with his passion for sports.

He had interned at as a junior at MIT, doing coding and programming, and ended up getting hired by ESPN as a software engineer after graduation. In his two years with the Bristol-based company, his claim to fame was creating the NBA Trade Machine, which allows people to play around and figure out which potential trades would work in the NBA. For hoop heads, it can be addicting.

“It’s kind of funny, it was sort of just a random project that was outside of my day-to-day responsibilities,” said Gupta. “I became pretty close with the NBA editors and they came to me with the idea. I thought it was really interesting and worked on it in my free time. I did a lot of research to learn all the rules of the CBA (Collective Bargaining Agreement) and how trades work and all that, and then programmed it up. I had no idea it would become what it did.”

During this time, analytics was just starting to take hold in the NBA. Teams were understanding the importance of deeper analysis and statistics that told a greater story than just points, rebounds and assists. Gupta wanted to be more involved in the wins and losses part of basketball, so he started looking around to see if he could break into the NBA.

Morey, meanwhile, was working in basketball operations for the Boston Celtics. He spoke to students and alumni at MIT about the work he was doing for the Celtics and Gupta drove up from Bristol to see the speech. Morey was essentially bringing baseball’s concept of “Moneyball” to basketball, or “Moreyball,” as it were. Gupta realized running an NBA front office with analytics as the backbone was exactly what he was looking for.

Gupta spoke to Morey after the speech and kept in touch with him.

“I was sort of hoping I would angle my way into a job with the hometown Celtics,” said Gupta. “Then Daryl completely out of the blue got the GM job in Houston. It was surprising. He wasn’t well known in traditional circles, but he was forward-thinking.”

When Morey was hired, he posted a few job openings for analysts to help build the Rockets’ infrastructure. Gupta applied and was hired, aided by his vast experience at ESPN and with NBA data.

Initially, Gupta’s day-to-day was to create a database with play-by-play data, historical box score data, college data and international data, and then build tools and reports to analyze that data. But because of his familiarity with the CBA, Gupta would present Morey with trade ideas and personnel ideas. Morey was open to it and Gupta’s role in the front office expanded. Over time, managing the salary cap and finding loopholes became more of his job description.

While working in Houston, Gupta also worked alongside Sam Hinkie, who served as the team’s vice president and executive vice president. Hinkie was second in command to Morey and was also a huge advocate of advanced basketball analytics.

In 2013, Hinkie became the general manager of the 76ers, and that opened the next door to Gupta’s career.

Gupta left the Rockets in 2012 to attend business school at Stanford. He joined Hinkie in Philly in the summer of 2013 as the GM’s right-hand man. Gupta finished his second year at Stanford, balancing that while working remotely for the Sixers.

Gupta was Philadelphia’s VP of Basketball Operations, and he happened to be in Philly for a now-infamous and somewhat controversial tenure known as “The Process,” in which the team went through a rebuilding phase that featured a lot of losing and a lot of draft picks.

“It was really special,” said Gupta. “For all that you hear in the public about Sam, most of it’s probably not true. The perception that Sam is this computer nerd who doesn’t know how to talk to people, it’s really the opposite. He’s a tremendous human being, an ethical, nice person who is super-easy to talk to. I consider Sam a very close friend. During that endeavor of ‘The Process’ in Philly, I basically felt like his partner. I got there about 10 days before the (2013) NBA Draft and he had gotten there maybe a month before that, and we had set our plan in place. ”

Essentially, the plan was to get younger, acquire many draft assets and build for the future, making wins in the immediate future a low priority. The first piece of the puzzle was unveiled during the 2013 draft when the Sixers dealt All-Star point guard Jrue Holiday to the New Orleans Pelicans for the Pelicans’ top-five protected 2014 draft pick and Nerlens Noel.

Over the next three seasons (2013-14, 2014-15 and 2015-16) the Sixers won a combined 47 games, including a 10-72 record in 2015-16. However, during those years they compiled a treasure trove of draft picks, including promising young big man Joel Embiid and point guard Ben Simmons.

There were constant accusations during “The Process” that the Sixers were tanking for draft picks and damaging the integrity of the game. In April of 2016, Hinkie stepped down from his post. Gupta stayed on for a few more months and then left to do some independent consulting. He was a special advisor for Morey and the Rockets last season.

The true genius of Hinkie and Gupta and “trusting the process” is now being seen by all after the Sixers and their young nucleus went 52-30 last season and advanced to the Eastern Conference semifinals.

“Sam would often joke that he was just the puppet GM and I was the real GM, which was him just trying to be nice,” Gupta said. “It was really a pretty awesome experience working with Sam in Philly and what we did was pretty unique.”

Gupta says he enjoyed his experience growing up in Billerica. His parents have since moved to Carlisle, and he has a brother and sister who live in Arlington. He keeps in contact with friends he grew up with.

In 2017, he gave the commencement speech at Billerica High’s graduation.

“It was a real honor,” said Gupta. “Before I gave the speech, I swung by the high school and caught up with Mr. Murphy, and he was telling me how they’re building a brand new high school, which is super exciting. He was saying they are trying to change the culture there. He grew up in Billerica, too, and I could relate to him saying when he was growing up it was always, ‘This person did well, in spite of Billerica.’ I always felt like that was the culture when I grew up, too. We wanted to get the message out that it’s not ‘in spite of Billerica’ it’s ‘because of Billerica.’ I truly believe that.”

Follow Matt Langone on Twitter @MattLangone