The Sinking of Old Ironsides: Winning the Discovery Fight and Losing the Case

September 21, 2026

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The Sinking of Old Ironsides: Winning the Discovery Fight and Losing the Case

The Massachusetts Appeals Court recently issued a useful reminder that aggressive discovery positions risk negative consequences far beyond facing motions to compel. In Old Ironsides Energy LLC v. Marsh & McLennan Agency LLC[1], the court affirmed summary judgment against a plaintiff seeking approximately $20 million in damages after concluding that the plaintiff lacked admissible expert testimony necessary to prove its claimed damages. The $20 million kicker? Expert testimony would have been admissible if the plaintiff had provided certain evidence to its expert witness and the other side—but earlier in the case, the plaintiff intentionally withheld that evidence as a litigation tactic.

The case arose out of a dispute between a private equity firm (plaintiff) and its insurance broker (defendant). The plaintiff contended that it had requested insurance coverage that would protect it against legal expenses incurred in responding to an SEC investigation, but that the broker procured coverage that protected only individual officers and not the company itself. When an SEC investigation later materialized, the plaintiff allegedly incurred substantial legal fees that were not covered by insurance and sued the broker.

What makes the decision particularly interesting is not the underlying insurance dispute—it is the discovery history.

Discovery Tactics

During discovery, the defendants sought attorney billing records and related materials supporting the plaintiff's damages claim. The plaintiff produced only invoice cover sheets and withheld the underlying billing entries on privilege grounds, asserting that the SEC matter remained active and that production could present risks in the investigation. It nonetheless produced a report from its own expert that opined on the reasonableness of the claimed attorney’s fees (even though the expert did not review the underlying invoices). Four years later in the litigation[2], when the defendant’s expert pointed out that the plaintiff’s expert did not have adequate support for his opinion, the plaintiff hastily gave the withheld fee invoices to its expert and the other side. Defendant moved to exclude the late discovery and plaintiff’s expert’s related opinion. The trial court[3] allowed the motion, explaining that “parties are not permitted to withhold documents based on objections, whether or not those objections are tested on a motion to compel, and then produce the same documents (or a subset thereof) when convenient to them.”

Plaintiff did not seek reconsideration, but it later tried to reproduce the legal invoices; the court prohibited that attempt and barred plaintiff from relying on “deliberately withheld material.”[4] As a result, the plaintiff’s expert report on the reasonableness of attorney’s fees was stricken for being “conclusory and speculative.” Without necessary expert evidence as to the reasonableness of fees,[5] there was no reliable way to calculate damages, so the BLS granted summary judgment to the defendant. The Appeals Court affirmed.

Lessons Learned

For parties and litigators, the most significant lesson is not that privilege claims or well-founded discovery objections are improper. They are often necessary and fully justified. Rather, the decision illustrates the danger of advancing broad objections as part of an aggressive discovery strategy without a parallel strategy for proving the elements of a claim.

Too often, litigants treat discovery disputes as isolated procedural battles. They resist production, stand on objections, and defeat individual discovery requests without stepping back to consider how those decisions will affect dispositive motions, expert opinions, or trial proof months later. Old Ironsides is a reminder that the court may eventually ask a simple question: if the documents quantifying your damages cannot be examined, how can the expert reliably support the claim?

The decision also highlights a recurring tension in commercial litigation. Parties frequently attempt to use privilege as both a shield against discovery and a sword to support affirmative claims. Courts have long been skeptical of that approach. Although the Appeals Court did not announce any new waiver doctrine, the practical result was the same. The plaintiff's decision to withhold key materials severely limited its ability to present admissible damages evidence. Winning the battle of not producing a particular set of discovery documents ultimately lost the war of trying to recover $20 million.

The broader takeaway for practitioners (and heads-up for parties or general counsel interacting with their litigation team) is straightforward. When objecting to discovery, especially discovery bearing directly on key case elements such as damages, counsel should always consider the downstream consequences. If billing records, internal analyses, valuation materials, or other core damages documents will ultimately be necessary to support expert opinions or trial testimony, a litigation strategy that succeeds in keeping those materials from the opposing party may simultaneously undermine the proponent’s own ability to satisfy its burden of proof. Discovery objections should be evaluated not only through the lens of immediate tactical advantage but also with respect to eventual admissibility. As Old Ironsides demonstrates, sometimes a victory in a discovery fight can contribute directly to a loss on the merits.

[1] Case No. 25-P-1075, 2026 WL 2444972 (Mass. App. Ct. Aug. 20, 2026) (Rule 23.0)

[2] Three years after the SEC investigation had concluded.

[3] The case was before the Business Litigation Session, a specialized Massachusetts trial court that hears complex business cases. Judges in the BLS rotate, and Judge Squires-Lee ruled on this particular motion.

[4] Judge Salinger issued this decision.

[5] The Appeals Court noted that assessing the reasonable range of expenditures in response to an SEC investigation is well beyond the common experience of a lay juror, and even of many attorneys. Without expert testimony, no damages figure could reasonably stand.

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The Sinking of Old Ironsides: Winning the Discovery Fight and Losing the Case

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