Trying the Bet-the-Company Case: Why Most Commercial Disputes Are Lost in Discovery

By Otto K. Hilbert, II

There is a comforting myth in commercial litigation that great trial lawyers win cases in the courtroom. Powerful cross-examinations, memorable closing arguments, the dramatic moment when the witness admits the document means what it says. In thirty-six years of trying complex commercial cases across twenty-three states, I have given a fair number of those closing arguments. I can tell you with some confidence that almost none of those cases were actually won in the courtroom. They were won — or lost — eighteen months earlier, in the conference rooms where document strategy was set, in the depositions where the record was made, and in the expert disclosures that quietly defined the trial.

When in-house counsel ask me what separates trial lawyers who consistently win bet-the-company cases from those who do not, my answer is rarely about courtroom skills. It is about the discipline of building a trial record from the moment the complaint is filed. The lawyers who win these cases are the ones who treat every deposition as if a jury will read it, every document production as if an appellate court will scrutinize it, and every expert disclosure as if it will be the centerpiece of a Daubert challenge. The ones who lose treat discovery as a negotiating sequence that precedes the real work of trying the case. They are wrong, and by the time they discover they are wrong, the case is largely decided.

The First Strategic Decision Is the Document Strategy

In any complex commercial dispute, the universe of potentially relevant documents is enormous. Email, instant messaging, calendar entries, draft contracts, internal memoranda, board materials, financial models, customer communications, and increasingly text messages and ephemeral messaging applications. The defense team that approaches this universe as a compliance burden — produce what is asked for, withhold what is privileged, fight about everything in between — has already made its first strategic error.

The document strategy in a serious case begins before the first production. It begins with a thesis. What story do the documents tell when read in the order plaintiff’s counsel will present them? What story do the same documents tell when read in the order we will present them? Where are the documents that complicate plaintiff’s narrative, and how do we ensure they receive the attention they deserve? Which documents in our production will plaintiff’s counsel feature in opening statement, and what is our response to each of them?

This work is not glamorous. It requires teams of associates reading documents that will never be exhibits, building chronologies, mapping document custodians, and identifying the patterns that the case file does not surface on its own. But it is the work that converts a document production into a trial record. When the case goes to trial, the lawyer who has done this work walks into the courtroom knowing every document the other side will use and how to defang each one. The lawyer who has not done this work is reacting to documents she has never read carefully, on a witness she has never deposed about them, in front of a jury that does not yet know which side is in control.

Depositions Are the Trial

I tell younger lawyers that depositions are the trial. That is not entirely true — the jury is not in the room, the judge is not enforcing rules of evidence, and the witness’s testimony has not yet been packaged into the form a fact-finder will see. But the deposition is where the testimony that will appear at trial is captured. If a witness testifies one way in deposition and another way at trial, the impeachment is automatic and devastating. If a witness commits to a position in deposition that we want them to hold at trial, that commitment is preserved in a record we can read to the jury.

The deposition strategy in a serious case requires understanding what each witness can give us and what they cannot. Some witnesses are deposed to lock in admissions. Some are deposed to expose gaps in their knowledge. Some are deposed to set up impeachment with documents they will not be permitted to explain at trial. Some are deposed because their testimony will never appear at trial, but their deposition will appear in a summary judgment motion or in cross-examination of a different witness. The lawyer who deposes every witness for the same purpose is missing most of the value of the discovery process.

I pay particular attention to corporate designees. The Rule 30(b)(6) deposition, in federal practice, is a tool of extraordinary power that is consistently underused by defendants and consistently misused by plaintiffs. The defendant who treats the 30(b)(6) deposition as a witness preparation exercise — pick the smartest available executive, prepare him exhaustively, and hope he does not blunder — has fundamentally misunderstood the rule. The 30(b)(6) testimony binds the corporation. It can be quoted at trial without calling a witness. It can be used to defeat summary judgment on issues the corporation thought it was conceding. The selection of the designee, the scope of the preparation, and the boundaries of the testimony are strategic decisions that should be made by trial counsel, not delegated to a litigation associate or, worse, to the witness himself.

The Expert Discipline

In sophisticated commercial cases, the experts often matter more than the fact witnesses. Damages experts, industry experts, accounting experts, regulatory experts, and increasingly data and forensic experts now drive the outcomes of cases that turn on complex transactions or contested market behavior.

The discipline of expert work begins with selection. The right expert for a case is not always the most credentialed expert, and is almost never the expert with the most jury appeal in the abstract. The right expert is the one whose actual professional history aligns with the opinions the case requires, whose prior testimony does not contradict the positions we need her to take, and whose Daubert vulnerability is lowest given the methodology she will employ. I have seen cases lost because the expert’s prior publications contradicted his trial testimony, and I have seen cases won because the expert’s contemporaneous consulting work supported the litigation positions the company needed her to support.

Once the expert is selected, the discipline shifts to the report. The expert’s written report — Rule 26(a)(2) in federal practice — is a document that will be tested at deposition, attacked on Daubert motion, and quoted at trial. It should be drafted with the same care as a brief. The methodology section should anticipate the challenges that will be made to it. The opinions should be stated with the precision they will need to survive cross-examination. The supporting data should be complete and reliable, because any gap or error becomes a basis for exclusion.

I have watched too many cases founder because the expert report was treated as the expert’s work product rather than as a team product. The expert provides the technical content. The trial lawyer ensures the report tells the story the case requires it to tell. That is not ghostwriting and it is not ethical compromise. It is the proper division of labor between an expert with deep substantive knowledge and a trial lawyer with deep knowledge of how testimony works in a courtroom.

Summary Judgment Is Not a Sideshow

Many trial lawyers treat summary judgment as a procedural waypoint between discovery and trial. File the motion if there is a chance of winning, brief it, lose it, prepare for trial. This is wrong. Summary judgment is the moment when the trial record assembled in discovery is presented to the court in its strongest possible form. Even when the motion is unlikely to succeed, the briefing exercise compels the defense team to organize the evidence, identify the gaps in plaintiff’s case, and frame the legal theory that will govern the trial.

Just as importantly, the summary judgment record becomes the appellate record for issues preserved at that stage. An appellate court reviewing a denial of summary judgment looks at the evidence the parties presented. If the defendant’s summary judgment briefing did not surface the documents and testimony that establish its defense, the appellate court will not see them in its review, and the trial record will be the only place those facts ever appear.

I file summary judgment motions in cases I expect to lose at that stage because the discipline of preparing the motion is part of preparing for trial. The brief becomes the trial outline. The evidentiary exhibits become the trial exhibits. The legal arguments become the jury instructions we will request. The motion’s denial does not waste the work; it accelerates it.

The Settlement Conversation Reflects the Trial Posture

In any complex case that has been thoroughly discovered, the settlement conversation will eventually become serious. The timing varies — sometimes after summary judgment, sometimes on the courthouse steps, occasionally during trial itself — but in nearly every case there is a moment when both sides assess the trial risk and consider whether resolution makes sense.

The position the defense takes in that conversation is a direct function of how well discovery was conducted. The defense that has built a comprehensive trial record, locked in adverse witnesses, and developed credible expert support negotiates from strength. The defense that arrives at settlement discussions with an incomplete discovery record, witnesses who were not effectively deposed, and experts who were retained late and prepared quickly negotiates from weakness, regardless of the underlying merits of the case.

I tell clients that the price of settlement is set in discovery. The litigators who built the record determine the leverage. The lawyer who arrives at the settlement conference for the first time, without the discovery context, is negotiating with information her adversary has spent eighteen months accumulating. She will lose that negotiation, and so will the client whose interests she represents.

The Trial Lawyer’s Discipline

What does all of this require? It requires that trial counsel be involved in discovery from the beginning, not introduced as the matter approaches trial. It requires that the document review be conducted by lawyers who understand how documents become exhibits, not by contract reviewers operating from a coding manual. It requires that depositions be taken by lawyers who have read the documents and know what each witness needs to give us. It requires that experts be retained early, briefed thoroughly, and treated as members of the trial team rather than as third-party consultants.

Most importantly, it requires the discipline to build the trial record even in cases that may settle before trial. The cases that settle are the cases that settle on favorable terms because the trial record made them too risky for the other side to take to verdict. The cases that go to trial are the cases that go to trial because the record forced them there. Either way, the work is the same.

In thirty-six years, I have not tried a case that I won at trial without first winning it in discovery. I have lost cases at trial that I might have won had the discovery been done differently. The pattern is consistent enough that I no longer think of it as a pattern. I think of it as the structure of how complex commercial cases actually work, and the discipline of bet-the-company trial practice is fundamentally the discipline of building, witness by witness and document by document, a record that the courtroom moments will rest on.

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Otto K. Hilbert, II is a Trial Attorney with AEGIS Law. He brings over 36 years of first-chair trial and appellate experience to representing clients in complex commercial litigation, securities defense, and regulatory enforcement matters. He has tried cases in 23 states and is admitted before the United States Supreme Court and multiple United States Courts of Appeals.

This article is provided for general informational purposes and does not constitute legal advice. Readers facing specific legal matters should consult qualified counsel.