They’ve Got Next: The 40 Under 40 - Rakesh Kilaru of Wilkinson Stekloff

July 14, 2021, 8:46 AM

Please describe two of your most substantial, recent wins in practice.
I was honored to represent Judge Emmet Sullivan in the mandamus proceedings arising out of Michael Flynn’s criminal case. Judge Sullivan couldn’t have been a more gracious client. The case moved quickly; we filed our opening brief on some complicated issues less than ten days after being retained. But our team worked seamlessly and with purpose and we were happy to ultimately deliver a win for the Judge and the judicial process.

I’ve also been representing Altria, the NCAA, the NFL, and a sovereign Indian nation in putative class action cases since the complaints were filed. We often come into cases closer to trial, but it’s been exciting and rewarding to develop the themes and narrative from the ground up.

What is the most important lesson you learned as a first-year attorney and how does it inform your practice today?
It’s OK to admit you don’t know the answer. In both of my clerkships, I would often receive challenging questions on a moment’s notice, as my boss was either preparing for argument or working through an opinion. It was tempting to shoot from the hip to show I was on top of everything, but I figured it was more important to get the right answer than a fast one. That instinct served me well, as often my (necessarily quick!) research revealed an answer different from what I had anticipated, or at least a more nuanced one. I’ve remembered this lesson every day, including when I started working in the White House with little idea of what an Executive Branch lawyer does, and when I began working at a trial boutique without ever having tried a case. It is particularly important in my current job, where it is paramount to maintain credibility with judges, clients, and colleagues and much worse to give the wrong answer than to admit you need some time to analyze or find the right one. This advice is the most common feedback I relay to young lawyers starting out.

How do you define success in your practice?
Litigation is a results-driven business, and so the easy answer is whether we win and/or whether our clients are happy with the outcomes we deliver. But I am also obsessed with process—with making sure we use a sound means for making sound decisions. Separate from results, I measure success by asking three questions. Are we being appropriately inclusive, by considering the views of everyone who has something to contribute and ensuring that our whole team has bought into our decisions? Did we see around the corners and avoid fire drills in the process of preparing a brief, an oral argument, or a witness? And was there anything the other side or the Court did that we hadn’t prepared for? These are ideals I strive for.

What are you most proud of as a lawyer?
Even though I am relatively young, nothing makes me prouder than when a more junior lawyer excels in front of a client or in the courtroom. I’ve been fortunate to have a variety of great platforms throughout my career and it’s always been a priority for me to help junior colleagues stand out. One example that stands out is a pro bono matter in which two associates at my firm were helping a man named Momolu Stewart seek early release from prison. Momolu had killed another man at a young age and spent his entire adult life in prison. But when he retained us, it was clear he was a changed man—he had spent decades focusing on his education and mentoring dozens of younger men and women on how to avoid the mistakes he had made. The associates led every aspect of the case, from developing a compelling evidentiary record, to writing a first-rate brief, to effectively presenting Momolu’s case in front of a packed courtroom. They deserve 100% of the credit, but along the way, I saw them implementing a few of my suggestions on executing a winning strategy, which—coupled with the result—was incredibly rewarding.

Who is your greatest mentor in the law and what have they taught you?
I had to pick one mentor, it would be Judge Sri Srinivasan. He is undeniably a brilliant lawyer and jurist, and remains the best oral advocate I have ever seen. But what has always stood out to me even more is his unfailing kindness and decency. I first met him when I was a paralegal at the Department of Justice, and he took time out of a busy day at the Solicitor General’s Office to get to know me. How many lawyers of his caliber would do that? He’s been an incredible sponsor throughout my career, and an inspiration that if you are a good person who does good work, great things will happen. I’d add that I am lucky to have many other incredible mentors, including my judges, my colleagues in the White House, and everyone I work with at Wilkinson Stekloff (particularly Beth and Brian, the founding partners).

Just for fun, tell us your two favorite songs on your summer music playlist.
My two-and-a-half-year-old daughter controls the family Spotify so the songs we hear most often are “Baby Yoda” and “Pancake Robot” by Parry Gripp, which I’d describe as annoyingly catchy.

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