Unrivaled 2025: Yolanda Garcia of Sidley

You served as co-lead counsel to XRI Investment Holdings LLC in Gregory A. Holifield and GH Blue Holdings, LLC v. XRI Investment Holdings LLC, litigation involving XRI’s $10.6 million loan to one of its founders in exchange for a security interest in the founder’s equity. Your team sued after the founder defaulted on the loan and a $4 million loan from a third party. Ultimately, in July 2024 the Delaware Court of Chancery awarded XRI $4 million in breach of contract damages. Can you tell us about your trial strategy?

This case was critical for XRI and many other clients, as it affirms the sacrosanct “pick your partner” principle of Delaware limited liability company law as well as other bedrock principles of business law. It had three parts. The first was the liability trial. Then we needed to get the Delaware Supreme Court to affirm our win. Then there was a remand for the damages portion of the case.

For the liability trial, we decided to focus on an argument that would help ensure enforcement of LLC rights crucial to maintain “pick your partner” principal rights as embedded in LLC agreements.

The trial court found in our favor but felt the Delaware Supreme Court should revisit its position on aspects of that principle. In the Delaware Supreme Court, we focused on how the court established the principle and why the court’s prior decisions to support it should not be disturbed. The court agreed. After remand, the damages trial was tricky. The judge had some expressed hesitation regarding our damages theory during the liability phase. We overcame that concern by unearthing extensive evidence that addressed his noted concern, and we ultimately prevailed. We won everything we asked for in the case.

Can you describe a major hurdle that happened during the course of this trial? How did you overcome it?

A major challenge came after the remand in the damages portion of the case. As I noted previously, we knew the judge was reluctant to award damages. That played out through some aggressive questioning from the judge.

We combed through the factual record of the original trial and by digging deep found evidence about why damages were compelled and appropriate. We presented it in a way that was effective with the judge acknowledging his prior ruling and asking him to reconsider with careful reasoning. The proof of our success came in the details of the ruling. That really was a satisfying and important victory for our client.

When did you first know you wanted to be a trial lawyer? What clicked for you?

I realized I wanted to be a trial lawyer in law school. I enjoyed public speaking from a very young age. During mock trials and moot courts, it really clicked how much I enjoyed being on my feet and striving to make convincing points about important issues. It came naturally to me, and I understood it was my true passion. I realized I could really make a difference using this ability. My path was clear.

What are the major keys to winning over a jury or a judge?

Tell a compelling story with a clear beginning, middle, and end that inevitably explains your legal arguments. The story is based on the facts of the case, but it must be interesting. Even the driest facts can be more effectively presented if told as part of a narrative. Whether addressing a judge or a jury, you must present the story in a way that seemingly carries your audience to the conclusion you want them to reach.

What’s the best advice a mentor lawyer or judge gave you about trial prep?
“An early mentor shared with me the Ralph Waldo Emerson quote: ‘When you strike at a king, you must kill him’ — meaning that first, try avoiding a one-way-to-win argument, but if it is unavoidable, plan the argument precisely and execute.”