A Sister's Eulogy

On September 27, 1986, the birth of my brother, Sandip Jain Gupta, disrupted my otherwise peaceful existence of four years. While many were charmed by Sandip’s wide eyes and adorable cowlick, I saw right through this boss baby: he was going to turn my world upside down. My fears materialized as Sandip outpaced me on all intellectual milestones. Reading before the age of two and navigating maps on family road trips before middle school, Sandip clearly had access to the deeper side of the gene pool. 

Since I could never win against my brother as a competitor, I made Sandip my accomplice instead. Rather than playing board games like Monopoly that pitted us against each other, I enlisted Sandip as my teammate in games such as Taboo, Outburst and Pictionary. His intelligence guaranteed my winning streak. Soon, I found that Sandip was not just my board game partner, but also a willing dance partner when I wanted to learn how to swing dance to Zoot Suit Riot - a questionable song choice. And he was a patient scene partner when I wanted to learn lines from movie scripts and act them out. If you’re ever in the mood to watch A Few Good Men, feel free to call me. 

My accomplice melted everyone. Sandip loved just sitting with you and watching the planes take off at airports, or riding the trains around and around. More than your admiration, he wanted your company in assembling toy trains or playing in the neighbor’s swimming pool. And he was quick to forgive when you hurt him. Like when we were jumping up and down on the bed and fell, Sandip hit his head and it started to bleed. While I was admonished pretty heavily by my parents, my brother’s only concern was that the drops of red blood would stain his favorite yellow sweater. Or at the ice skating rink where we practiced, I keep thinking of this time when Sandip was hit by one of the older kids who was doing a spiral move and crashed into him. The skater’s blade hit my brother’s temple, and the pain prompted Sandip to burst into tears. But once we confirmed Sandip did not need to go to the hospital, he just carried on with practice and held no ill will against that skater. 

All those same qualities carried into his adolescence. Every teacher who had Sandip in his or her classroom usually had me four years prior. It was “fun” to witness every teacher run the same gamut of emotions in under a minute as they realized we were siblings. The teacher would initially be dazzled by Sandip’s brilliance, then be surprised to learn we were related, and finally, confused why Sandip did not seem to need their approval in the same, Type A way I did. Sandip’s perfect scores on all his aptitude tests and accolades across his extracurricular activities, such as debate, piano and choir, earned him more awards than could fit on the mantle – so much that we still have boxes of his trophies in the attic to this day.

Regardless, or maybe because he was so smart, Sandip knew that impressing people was not worth his time compared to solving real problems and enjoying the company of friends. I was re-reading one of his emails from 2009 and he wrote, verbatim, “my goal is to do something that will make a difference for people.”  As he grew into adulthood – and perhaps because of some of his own experiences or things he witnessed – he became keen on reforming health care. At UT Austin, he was one of the first organizers for the Obama 2008 presidential campaign, when the dream of the Affordable Care Act was still in the embryo stage. 

Sandip’s work at Compass, Alight and Garner all had a single unifying theme – do health care better. I remember when Mark Cuban launched Cost Plus Drugs – Sandip clearly had some notes for Mark.  So many smart people in the world had yet to solve this problem, but I 1000000% believe that if Sandip had a chance to live his full life, he would have truly changed the way health care worked in this country.

Aside from his professional problem solving, I think Sandip also personally wanted to help people feel … less lonely. He continuously brought people together. In this past year, I cannot tell you how many people have reached out to me, sharing how Sandip brought them into his circle, and made a place for them – whether with an invitation to trivia night, to join a running crew … or simply to join him for lunch. One person wrote how Sandip was a big part of helping him get through a really awful period of his life. Another told me flat out, “I would not be alive today if not for Sandip.” The resounding theme of anyone who shares a memory is KINDNESS. 

I am heartened by these shared memories, but never surprised. It was always a party when Sandip would come visit me in New York. After taking in multiple Broadway shows together, we would host a dinner party and game night at my home. My friends started to ask when Sandip would be back in town next. They couldn’t wait to hear his take on the state of the world while gobbling up his eggplant parm. They loved that because of him, I finally had cookware in my kitchen and learned how to make eggs for myself. They also couldn’t wait to see him push my buttons to defeat me in every single board game we played, as he refused to remain my accomplice once he realized I was actually the one holding him back ;)

I think we the best way to characterize our relationship in adulthood was an iron-clad alliance. When we had a problem, we strategized together on how to solve it. When I hit a wall at Google and knew I would have to leave the company, I called Sandip for sage advice on how to pen my whistleblower letter. The amount of redlines in the edited draft he returned made me cry, but in a good way. Only someone who cared like Sandip would take the time to provide such thorough and meaningful feedback. When our dad faced the prospect of surgeries to remove the tumors in his colon or to repair his spine, Sandip led the charge on researching medical options and recovery practices while I took on logistics and hospital night shifts. We were a team – and together, we were unlimited. But out of thirty-eight years of memories, the most remarkable is the meta-memory of the sheer volume of love he gave to me, and I felt for him, across those years. 

But regardless of my loss, worse is the future Sandip himself lost. The one I know he wanted, and so richly deserved. He wanted to launch his own successful business, either in the same health care cost containment field or in deploying software as a service to debate tournaments. I kept trying to pitch him on a brother-sister law firm, where he’d run the business and I’d tackle the lawyering. “Think of it, Jain & Gupta!” I would say. And I could tell he was considering it because his only response was, “that’s not what we’re gonna call it, is it?” (Sorry Mom and Dad.) We discussed politics – and agreed that if I ran for office, he would be my campaign manager. And then, because I’d of course win with him at the helm, he’d subsequently be my Leo McGarry too. That was his professional future.

On the personal front, Sandip had also saved to buy a new house in cash to avoid the encumbrances of a mortgage because he wanted to be ready for the next wave in the housing market. Sandip had just decided he wanted to start dating again to meet a partner with whom he could travel the world and build a life at home. One of my greatest honors in the Fall of 2024 was seeing Sandip get “on the apps,” as the kids say, and then being solicited for input on which way he should swipe per match. My privilege was swiftly revoked, but I knew that Sandip would make a wonderful partner to any woman lucky enough to win his heart. Most of all, Sandip wanted to become a father - perhaps because of how much he loved his own. Sandip wanted to help young ones navigate the world, and discover the world again through his children’s eyes. In short, Sandip wanted to live. 

If Sandip himself was a Broadway show, the lights went out at intermission and, for reasons that cannot be explained or justified, never came back. So, we’re going to have to write a banger of a second act for him. Sandip, my brilliant, beautiful, big-hearted brother, my first, longest and best friend, my fallen comrade, thank you for being who you were. As our friends would say, “it’s been a pleasure doing sister business with you.” I will love you forever.