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Sachin Gupta's "dream" has been to be in charge of an NBA team's basketball operations.
From the time he was helping develop ESPN's trade machine, to earning his MBA from Stanford, then finding previously unseen ways to execute trades around the collective bargaining for Houston, Philadelphia and Detroit, this was always the goal, no matter what team it was.
That it happened in Minnesota, where Gupta has made a home the past two years with his wife, Anuja Singh, gave the honor extra significance.
"Any one of these 30 jobs is beyond imagination," Gupta said. "But this one in particular is so special for me."
It's special even amid the unusual circumstances Gupta, 40, earned the job. He has to impress not one but two ownership groups — first Glen Taylor, then Marc Lore and Alex Rodriguez, who are on a path to becoming controlling owners in 2023. While they have expressed confidence in Gupta running the operations following the Sept. 22 firing of former team president Gersson Rosas, they have not named Gupta the permanent successor, a process that can still take months, Lore said Friday. They also left his title — executive vice president of basketball operations — intact.
"I think there's great core value alignment," Lore said. "He's a very smart guy. Been around a long time and excited to spend more time with him, get to know him better."
Rosas made all signing and trade decisions over the summer and shaped this season's roster in his vision. If Gupta is going to impress his bosses, it won't be with splashy signings or deft maneuvering around a draft. Instead, he will have to make that impression in how he helps the current roster succeed, and recalibrates the tone of a workplace that Rosas left at best in conflict and at worst demoralized, sources said. Gupta will have to make that impression with his character, intelligence and demeanor.
If there is one move out there that would allow Gupta to leave a big imprint, it would be trading for disgruntled 76ers star Ben Simmons. But Gupta isn't interested in trying to make a big mark for the sake of it.
"I couldn't ask for anything better, "Gupta said. "I don't view it as like, 'Oh I've got this for a time. I've got to try and prove myself and I've got to make a splash quickly and try to save the job.' "
Instead, he plans on taking the same approach to being the Wolves' basketball boss that he has throughout his career — by not being full of bravado, but by being diligent, synthesizing many points of view and listening more than he talks.
Said former NBA executive Ben Falk, who worked with Gupta in Philadelphia: "He's a very powerful leader in a way most people wouldn't recognize as leadership unless they really thought about it."
Falk remembers the first time he and Gupta had a conversation. It was at the Sloan Conference, the analytical Super Bowl, and instead of sticking to sports, Gupta and Falk veered into philosophy of life. This can be Gupta's conversational style — it can take you in different directions, Falk said, and he asks insightful questions.
"If you said that about someone else you might think it's some uber intellectual who wants to turn everything into a metaphysical discussion or something. But it's not that," said Falk, who runs the analytical website Cleaning the Glass. "When you talk with him, you want to slowly keep talking, unpacking whatever it is you're talking about. He's genuinely curious. He'll keep asking you questions and keep digging and so eventually you're going to hit something that gets pretty deep."
That goes for Gupta's basketball acumen as well. In Philadelphia, Gupta would sometimes be the last one to speak in meetings. He'd sit back, absorb information from everyone else speaking in the meeting and when he would speak, what he said carried a lot of weight.
"Above all he's humble and I think he knows when to ask questions," said Daniel Adler, an assistant GM of the Twins who has been Gupta's friend for years.
Gupta said he isn't about to change his style now that he's the one making final decisions instead of advising someone like Rosas, former 76ers GM Sam Hinkie or Sixers president Daryl Morey, the former Rockets GM.
"I see [listening] as being even more impactful," Gupta said. "It's more important that I do that in this role being the final decision-maker to make a concerted effort to get all the viewpoints that exist … across the whole org."
Sources said it wasn't always that way under Rosas, who frustrated some by seeming to diminish the input from his staff. Gupta and Rosas had a contentious relationship in recent months — Rosas blocked Gupta from taking a job with Houston in June — but had come to an understanding on working together before Rosas' dismissal.
Gupta said the concept of "servant leadership" is important to him and sees his role as trying to uplift the organization. He brought back longtime scout Zarko Durisic, a source said, after Rosas and Durisic couldn't come to an agreement on a new deal and Durisic left, a move that rocked morale around the organization.
"The core of [servant leadership] is understanding this is not about me," Gupta said. "This is about the team and trying to put the team in the best position to succeed … and that includes not just resources, but making sure the environment is what it needs to be, the culture is what it needs to be and people are excited to come to work."
Gupta has called coach Chris Finch an "ideal partner" to work with as they get ready for the new season. The two go back about a decade, to when Finch was coach of Houston's development league team and Gupta was helping him experiment with different analytic-driven concepts and styles of play.
"No egos," Finch said. "Just easy to work with, just generating ideas out of thin air about how to look at the game differently."
That goes back to the first project Finch and Gupta worked on together, which revolved around corner three-pointers and identifying where the highest percentage of passes came from on the floor to result in corner threes.
"He mapped it out," Finch said. "He 'gridified' the half-court and had all different color zones about the best way to create open corner threes from where you were passing on the floor."
Finch said, in his experience, Gupta considers input from coaches more than the norm.
"A lot of front offices will not value coaching staffs in that regard because they feel they're too close to the players," Finch said. "But he's just the opposite. He thinks that's where we have the most to learn because we have this innate and unshared knowledge of these guys and our opponents."
Gupta also used the same term Finch used to describe their relationship — "no egos."
"He's open to listening to any ideas I might have knowing that it comes from a good place and it's never me dictating or telling him he has to do X, Y or Z," Gupta said.
Gupta said he doesn't want to be "dogmatic" when it comes to building a team. There is no set correct way, even with analytics. A team has to be flexible, even as Gupta believes in many of the same general principles Rosas did — playing with pace, shooting threes, getting to the rim and the foul line. Those goals won't change.
"Information changes. Variables change," Gupta said. "As the roster changes you may need to update some of those philosophies. It's always about maximizing, the way I view the on-court strategy is trying to maximize the skill set of the players you have."
While Gupta said he isn't looking to make roster moves for the sake of making them, there is one situation that will have his attention: Simmons. Gupta can't comment on any specific trade scenario, but in general he said it was fair to say free agency "may not be the primary angle for player acquisition" for the Wolves. Rosas often said trades were the major way to rebuild a roster in Minnesota, where big-name free agents rarely, if ever, come.
Gupta will keep open the lines of communication with Philadelphia, sources said. He maintains good relationships with those in Philadelphia, many of whom he has worked with previously.
Speaking more broadly about trades, Gupta said existing relationships can help in negotiations.
"It is very important in terms of being able to get to a deal point," Gupta said. "It takes a lot of trust on both ends to get to that point."
To get Simmons, the Wolves might have to execute a multi-team trade if another team can offer Philadelphia it desires. Luckily for the Wolves there likely isn't anyone better at coming up with unique trade structures than Gupta. At every stop along the way, Gupta has dazzled colleagues in that category.
"It's like magic when you're watching him," Falk said. "And you're like, 'I don't know the answer to this,' and he'd come up with [a framework] that I wouldn't know how to think about … and it wouldn't seem like it took a lot of effort."
The key, Gupta said, is looking at trades from the other team's point of view and giving them something to incentivize doing the trade.
"That part is really satisfying to me. I really enjoy it," Gupta said of coming up with trade structures. "It gets the juices flowing. It's sort of like trying to solve a puzzle."
If he were to get a deal in place, Gupta would likely have to inform and explain his thinking two sets of owners of the trade. That part of the job, Adler said, is one of the most important for any head of an organization, like with Twins President Derek Falvey and owner Jim Pohlad.
"I view a really a huge part of Derek's job is making sure that Jim knows what's happening, isn't surprised by our moves and understands what our process is regardless of the outcome," Adler said. " That's an extremely important job. … Now you're talking about two different ownership groups … it is definitely a high degree of difficulty on that level I would say."
But Adler, who also worked in the NFL, said Gupta has the skills to pull off that balancing act.
"His humility will take him really far," Adler said. "Of course he's extremely smart and any chance to find an edge through an intricacy of the collective bargaining agreement or something analytical, I think he's going to be at the forefront of discovering any of those edges. That's a great advantage for the team."
Gupta got a vote of confidence from Taylor and Lore at media day, with Lore saying, "I've already started to build a relationship with Sachin, and he's quite a talent. He also exhibits many of the core values that we're looking to instill in this organization."
To hear those that know Gupta tell it, he has been that way throughout his career, and just because he's now in the big chair, he won't let that change him.
Lore said he wants to come up with the organization's "three core values" before launching into the process of picking a permanent head of basketball operations. That process, which began over the summer, could take six months or even up to a year. In the meantime, Lore, Rodriguez and Taylor are comfortable with the team in the hands of Gupta, who wants to prove he can do it beyond this temporary time.
"I don't view it as like I have this fixed amount of time to prove I can do this job or I'm the right person for the job," Gupta said. "I'm confident in my abilities and I view it is as ... doing the best I can and putting the team in the best position to succeed long term."
No matter how long he is here.