Let's Make A Deal

Monday October 20, 2008 0:16 AM

Let's Make A Deal

Meet the man behind the ESPN trade machine

Jason Friedman
Rockets.com Staff Writer

HOUSTON - If you’re a hardcore NBA fan, chances are you’ve sacrificed countless hours of productivity while playing with ESPN.com’s trade machine; an ingenious tool which allows armchair GMs to summon their inner Daryl Morey as they craft and concoct everything from the straightforward one-for-one player swap, to something as convoluted as a four-team deal involving a smorgasbord of players, bloated contracts and cash considerations – all done within the confines of the NBA’s current collective bargaining agreement.

For some, the trade machine is merely an amusing diversion; a good way to kill some free time. For others, like ESPN’s Bill Simmons, its allure creates something altogether closer to obsession, as witnessed by the countless columns the wildly popular writer has devoted to his own wheelings and dealings with the device.

It’s all a testament to the trade machine’s creator – a 26-year-old MIT graduate named Sachin Gupta. But if you’re feeling so inclined, don’t bother sending thank you letters to ESPN headquarters in Bristol, Connecticut. Though Gupta is still helping others pull the trigger on blockbuster deals, these days his work has a far more tangible application. His title: basketball operations developer with the Houston Rockets. His role: assisting Morey and the rest of the Rockets’ braintrust in their quest to build a championship-winning team.


Like pretty much every other high school senior in America, Gupta didn’t know what he wanted to do with his life. Then again, not too many teenagers have the wherewithal to eventually translate that sort of indecision into a computer science degree from MIT. And while the prestigious Cambridge campus isn’t exactly known as the cradle of NBA careers, it helped launch Gupta, in more ways that one, onto the path which would one day lead him to Houston.

The first key moment took place before he’d even graduated from college. A lifelong sports nut, Gupta parlayed his passion – along with his computer science expertise - into a software engineering gig at ESPN. That opened up a host of other opportunities. With his foot in the door, the Boston-native went out of his way to befriend the network’s crack basketball staff.

“I stepped out of my engineering role a little bit to try to get more involved in the basketball side of things,” says Gupta. “I eventually developed a close relationship with some of the NBA editors and writers like Chris Ramsay, Royce Webb, and John Hollinger. I have to give those guys a lot of credit for giving me the chance to contribute and including me as part of their team.”

So Sachin pulled double-duty for awhile. In addition to his engineering responsibilities, he took on various side projects for ESPN ’s basketball staff. One such project landed on his plate about a month before the 2006 NBA trade deadline. ESPN wanted to figure out a way for fans to fully engage themselves in the deadline drama. The solution was simple. The trade machine was born.

“Chris Ramsay, who runs the NBA section, came to me with the idea of building an application to let fans get a little closer to the game by playing GM and trying out different trade scenarios. I thought it was really interesting so I kind of took the idea and ran with it. I spent days just studying the CBA and learning all of the ins and outs of the trade rules. I don’t think anyone had any idea how popular it would end up becoming. I’m sure the fact that Bill Simmons and Chad Ford started using it in their columns really helped it take off.”

But while the trade machine was a huge success for ESPN, Gupta was already contemplating ways of using his skill beyond the realm of Bristol.

“I knew that basketball was starting to take after baseball in terms of using analytics to gain an advantage and I felt like the things that I was working on could be valuable to a team,” explains Gupta. “Though I liked the idea of my work being viewed by so many people at espn.com, I really wanted to get closer to the game and help a team win.”

Enter fellow MIT product Daryl Morey.

Gupta and Morey first met in March of 2005 when Daryl – then a member of the Celtics’ operations staff – was the guest speaker for a small alumni gathering. The two kept in touch via email until Morey moved on to his current position as GM of the Rockets.

“I was blown away by Daryl’s presentation about the things that he was working on with the Celtics and I knew immediately that he was someone that I needed to keep in touch with in the future. So I would send him emails occasionally to let him know about the latest things that I had been working on, and he was always very responsive even though I’m sure he was extremely busy with his responsibilities with the Celtics. I knew that the analysis that he was doing was far beyond anything I was sending him but I always appreciated him taking the time to consider my analysis.”

“So needless to say, once he got the job [in Houston], I immediately got in touch with him to congratulate him and then applied for the job that I have now. I was very lucky that my work at ESPN really prepared me for this job so it just worked out perfectly for me.”

Gupta started working for the Rockets in June of 2006. As part of his duties, he manages the Rockets’ database and produces reports which analyze the team, opponents, trade options and draft-eligible players. It’s a lot of work, but the gig comes with its fair share of perks – such as living every sports talk radio caller’s dream by being able to discuss deals with the guy pulling the trigger.

“Though my work is mostly objective and doesn’t involve me giving my own personal opinion, Daryl and [Vice President of basketball operations] Sam Hinkie are both very open to hearing what I think. I think they like the fact that I bring a different perspective to the group, even though I may not be right. Daryl and Sam are both very open-minded and they want to make the best decisions possible regardless of who comes up with the ideas. Especially since I got to know the trade and salary cap rules pretty well while building the trade machine, they listen to my ideas about trades and free agency, and respect my opinion about players who I think may be undervalued.”

And precisely what type of player is undervalued?

“Chuck Hayes has always been one of those guys,” says Gupta. “A lot of things just can’t be measured in the box score stats. So one thing that we like to do is measure a player’s impact by seeing how the team performs when he’s on the floor versus when he’s off the floor. And Chuck is always a guy who, when he’s on the floor, the team just wins. He may not have a direct impact by putting up big points, but when he’s on the floor our defense is better and he makes the hustle plays that help us win games.”

“In general, defense is what’s not captured in the box score, so defensive players are probably the ones who are most underrated in the league.”

Sachin says he tends to focus on efficiency and usage whenever he’s conducting his own analysis, and cites a pair of current Rockets as prime examples of players who stand out when placed beneath his microscope.

“I’ve always liked players, like Shane Battier and Brent Barry, who may not be the first offensive option but are going to score points efficiently with the opportunities that they get. On the other hand, I’ve never been a big fan of players who are often considered stars but force up bad shots to get their share of points. To be fair, it does get harder for a player to score efficiently when he is the focal point of the offense and opposing defenses are keying on him, but you have to remember that basketball is a team game. We’re very lucky because our superstars – Tracy, Yao, and now Ron - are very unselfish and know that they can trust their teammates to score efficiently when opponents are overplaying them.”

He’s not alone. Efficiency has been the buzzword of the basketball community – at least those inclined toward statistical analysis – for a few years now. It’s even starting to creep into the mainstream. And as these ideas take hold, it will only serve to open up more doors for people just like Gupta.

In other words, the ESPN trade machine was just the beginning.

“Everyone wants to be a GM, but I just love working in basketball for a team. Eventually I would love to do more with trades and free agency, as well as become more involved with the CBA and salary cap management – that’s the part of the job that I enjoy the most and I hope to do more of it in the future. But right now, I just want to continue on this path of pushing our focus on analysis and doing whatever I can to help us win more games and hopefully bring home a championship.”

Have a question for Rockets.com? Send it to Jason Friedman via email at: jasonf@rocketball.com.

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