In their first public pronouncements after formally acquiring Chelsea in May 2022, Clearlake Capital co-founders Behdad Eghbali and Jose E Feliciano pledged to “expand the club’s investment across infrastructure, technology, and sports science to support the incredible Chelsea football and commercial teams — all with the goal of leveraging this growth to fuel even more on-pitch success”.

On-pitch success remains an aspiration rather than an achievement for the talented young squad showing fresh promise under head coach Enzo Maresca. But the investment that Eghbali and Feliciano promised is ongoing, undeniable and not limited to the frenetic transfer activity that has dominated headlines.

A key element of Clearlake’s plan from the outset was to dramatically improve the quality and scale of Chelsea’s data analytics to inform every aspect of the sporting operation, from performance and injury prevention to player recruitment. That push has now led them to hire Sachin Gupta, executive vice president of basketball operations for the Minnesota Timberwolves and one of the most highly regarded analytical minds in the NBA.

The upcoming recruitment of Gupta may raise a few eyebrows in the football world, but Clearlake have repeatedly shown a willingness to look outside the sport to find the individuals they believe are best qualified to drive Chelsea forward in their specialist fields. Two of the more prominent examples include Jason Gannon, former managing director of SoFi Stadium, who now serves as the club’s president and chief operating officer, and Aki Mandhar, hired from a senior executive position at The Athletic earlier this month to be the first dedicated chief executive officer of Chelsea Women.

Gupta’s challenge will be to bring his analytic and strategic expertise to football, but there can be no doubting the credentials he established as a basketball executive.

In many ways, Gupta serves as one of the faces of the changing times in the NBA over the past 15 years. His parents came to the United States from India in the 1970s and settled in Boston. Sachin is the youngest of three children and he got swept up in the fervour of a sports-mad town when he was a kid.

He went to Massachusetts Institute of Technology (MIT) to study computer science in college, but from the beginning hoped to find a way to pair it with his love of sports as he entered the working world. He started as an engineer at ESPN, where he wrote the code for the NBA Trade Machine, a wildly popular module that allowed fans to construct trades of their own making and check to see if they met the byzantine criteria of the league’s collective bargaining agreement to make them realistic ideas.

He entered the league in the think tank that was the Houston Rockets organisation, working in a front office led by Daryl Morey, who now runs the Philadelphia 76ers. Morey ushered in a new era in the way basketball front offices were staffed and thought about the game, emphasizing analysis with deep dives into data to complement the eye test applied by more conventional scouting.

When Gupta heard Morey talk about his philosophy at a sports conference before he was hired, he said it sounded like “Moneyball” for basketball.

“Oh my God, this is it,” Gupta said to The Athletic in 2019.

Morey assembled a staff that would eventually spread around the league as teams worked to catch up to the Rockets’ way of examining the game. That included former lieutenant Sam Hinkie taking over in Philadelphia and implementing a controversial strategy that came to be known as “The Process”. It involved constructing a team aimed at landing high draft picks that could become the No. 1 star that every team needs to be a contender.

Hinkie hired Gupta as his second in command and the two set about putting teams together that lost a lot of games, traded established players for future draft picks and amassed assets. The boldness of the play earned the front office admiration from some of the more out-of-the-box thinkers in the league and derision from more conventional observers. The strategy did lead to them drafting Joel Embiid in 2014, but Sixers ownership ultimately lost patience with the long play and parted ways with Hinkie.

Gupta went on to work briefly for the Detroit Pistons and was then hired in Minnesota by Gersson Rosas, one of his confidantes from his Houston days. He has always been targeted for his creativity with trades and his expertise in building analytics departments.

Gupta has always been targeted for his creativity with trades. (Courtesy of Minnesota Timberwolves)

In looking for a glimpse into how Gupta may integrate himself into a new club, a new country and an entirely new sport, an answer he gave in 2019 may provide an indicator. Those who are deemed to be on the analytics side of basketball are often accused of taking the human element out of sports, of ignoring personality and makeup while basing all of their evaluation on statistics and measurables. Gupta insisted that is not how he approaches the job.

“Ultimately it’s humility. I think that’s where a lot of people have issues, particularly if a new analytics person comes in guns blazing,” he said then. “This is what the numbers say. This is what the model says. You’re wrong, this is right.

“First of all, you’re not a very good analyst if you have that much confidence. The models don’t know anything about personality or fit and all that.”

The five years he spent in Minnesota were eventful. He arrived in 2019 to work with Rosas, who he got to know well when they both worked in Houston. The two set about making sweeping changes to the roster and the organisation to bring one of the league’s long-struggling franchises into competitiveness. By the middle of their first season on the job, they had traded all but two of the players they inherited from the previous regime. Rosas led a front office that hired coach Chris Finch, drafted Anthony Edwards and Jaden McDaniels, and signed Naz Reid as an undrafted free agent. The three of them comprise a major part of the core of a Wolves team that has become a contender in the Western Conference.

But two years into his tenure, Rosas started to meet resistance from inside the organisation because of his leadership style, which led to a messy exit from the team days before training camp in 2021-22. Gupta was elevated to run the team on an interim basis and he and Finch stabilised the team after the Rosas fireworks and helped the Wolves reach the play-offs for just the second time in 18 years. Gupta also beefed up the team’s analytics department, assembling one of the more robust staff in the league.

Gupta hoped to parlay that season into the full-time job, but the Timberwolves decided to go after a bigger name and lured Tim Connelly away from the Denver Nuggets to take over. Gupta remained on for the next two years and the Wolves made the play-offs both seasons. They advanced to the conference finals last season for the second time in the club’s 35-year history.

Under Connelly, Gupta remained in charge of strategy and analytics but was bumped down the organisation chart as Connelly brought in some of his people from outside. He also was the victim of a bizarre robbery last season when a former team employee pleaded guilty to stealing a hard drive from Gupta’s computer.

This is the boldest move yet for Gupta. (Courtesy of Minnesota Timberwolves)

For Gupta, joining Chelsea may be the boldest move yet in a career filled with them. He spent 18 years in the NBA, climbing from a special adviser with Houston in 2006 to the No. 1 spot in Minnesota in 2021-22. He could have stayed with the Timberwolves, where he was under contract for another season, but the opportunity to live in London with his wife, Anuja, and their young daughter, bring his analytical expertise to a prestigious club like Chelsea and tackle an entirely new sport proved too much to pass up.

The game is different, but the search for answers remains the same.

“The thing is that there’s not really a right answer,” Gupta said in an unpublished comment to The Athletic in 2019. “We’re just trying to get to the best answer. It’s not that there’s a right player to draft, a wrong player to draft. We’re trying to get there. The way I think about the world is all in probabilities. We’re trying to gain small probabilities anywhere we can.”

Clearlake will be hoping that Gupta will help give Chelsea the kind of edge that can make their promised on-pitch success a reality.

(Top photo: Courtesy of Minnesota Timberwolves)