May 19, 2021

When is it Time to Hold and Time to Fold?

Subscribe to Our Newsletter

Newsletter


Dean Gresham

|

May 19, 2021

The settle-or-litigate conundrum

A victory, in complex litigation, is sometimes difficult to distinguish from a Pyrrhic victory.  King Pyrrhus won the battle, but his army suffered such heavy and irreplaceable losses that he was forced to abandon his campaign against the Romans. High stakes litigation can easily drag on and the accumulated attorney’s fees and discovery expenses can end up approaching or even exceeding an amount that might have resolved the dispute months or even years earlier. 

There is no science of knowing when to litigate and when to settle. Every dispute presents its own difficulties and opportunities. Although we know almost all litigation settles before trial, there will always still be some cases with no workable path to compromise. Moreover, even when settlement is clearly in the cards, there is never a perfect time to settle.

The Courthouse Steps

A critical last-minute ruling from the court will sometimes push the parties toward a compromise they had avoided for years. However, such eve-of-trial settlements seldom survive the scrutiny of hindsight. After all, it takes a lot of time and money to reach those courthouse steps. Too often, parties realize that they failed to explore earlier opportunities to resolve the case. A useful way to approach the settle-or-litigate conundrum is to remain wary of any case snowballing all too predicably toward another and costly eve-of-trial settlement that might be resolved earlier and far more efficiently.

The Bigger Picture

Litigation does not take place in a vacuum. Decisions about courtroom tactics and settlement approaches need to be consistent with the near, and long term, goals of the company. Time spent dealing with a lawsuit can reduce the productivity of key employees. Litigation can impact business relationships, funding and investors, stock prices, insurability and more. Sometimes the need to settle is driven by a need to get back to business.

The Cost of Discovery

There are two sorts of costs to discovery during litigation. First, there is the money.  Discovery is the most expensive aspect of litigation and, in many complex matters, can readily provide its own justification for pursuing settlement. Second, there is the disclosure aspect. Discovery often means sharing information a company would prefer not to share. There is no reason to actually incur all costs of discovery before including them in settle-or-litigate calculations.

Merits and Money

Don’t overemphasize the strength or weakness of an opponent’s legal position. Your perception of the merits of a case must always be weighed with not only the amount at stake but the cost of further litigation. It is often far better to pay a smaller amount to settle a case instead of spending a great deal of time and money just to “win.”

Creative Solutions and Litigation Insurance

An exorbitant demand for X and a stingy counteroffer for Y. There are more creative ways to get deals done. When deciding to settle or litigate, consider the availability and cost of litigation buyout insurance that can replace the uncertainty of litigation, long before any settlement is reached, with a known, fixed cost. In the class action context, remember that a claims-made settlement can be designed in any number of different ways. Work with class action experts and develop a settlement structure that makes the most sense for your organization. Keep in mind that insurance is available even after a settlement is reached to absorb the risk of a claims-made settlement. 

If your company is facing uncertainty because of litigation and you would like to explore strategies to minimize that uncertainty, please  contact us  to discuss how we may be able to help.

Certum Group Can Help

Get in touch to start discussing options.

Recent Content

People in a meeting room, sitting around a table, brainstorming. Glass wall reflects outside.
By Certum Group Team December 4, 2025
Certum Group, a leader in litigation risk management, is pleased to announce the launch of Certum Legal Solutions (CLS), a managed services organization (MSO) that helps law firms handle their day-to-day operations. CLS expands Certum Group’s platform beyond litigation finance and insurance into technology-driven operational support for law firms. With this launch, Certum is now the only provider to offer funding, insurance, and operational services through a single, integrated platform. Built by trial lawyers and experienced legal operations professionals, CLS delivers end-to-end support for mass tort and single-event litigation practices, including intake, pre-litigation investigation, plaintiff discovery support, settlement claims processing, and client communications. The CLS platform leverages proprietary and heavily customized tools such as integrations for rapid medical record collection, a mobile client app, automated document workflows, electronic signature systems, and an in house call center to streamline case management and boost efficiency. CLS currently manages thousands of cases for law firm clients across the United States and is designed to scale quickly to meet changing caseloads while maintaining control and delivering a consistent client experience. “Our clients have long relied on Certum to mitigate litigation risk and financial risk; with Certum Legal Solutions, we can now mitigate operational risk as well,” added David Diamond, Managing Director at Certum Group. “Because CLS is built the way trial lawyers think about building cases, from intake to resolution, firms get a turnkey, technology forward solution that measurably improves efficiency and outcomes,” said Asim M. Badaruzzaman, CEO of Certum Legal Solutions. CLS originated from a services operation launched in 2024 and was acquired by Certum Group in 2025. The new business line uses a customized fee for service model that aligns pricing with the scope and value of each engagement, allowing firms to avoid the capital costs and staffing requirements of building these capabilities themselves. While the initial focus is on mass tort and single event, Certum plans to extend CLS capabilities to additional practice areas over time, further expanding the company’s comprehensive approach to funding, insurance, and operational support. For more information, please contact: David Diamond Managing Director, Certum Group ddiamond@certumgroup.com Asim M. Badaruzzaman CEO, Certum Legal Solutions asim.badaruzzaman@certumlegalsolutions.com
A gavel rests on top of a stack of US one-hundred dollar bills.
By Kirstine Rogers November 6, 2025
The recent legislative push—then retreat—to impose a tax on litigation funding returns didn’t change the law, but it clarified what’s at stake. It shined a spotlight on the solution that litigation funding provides for the legal industry and to intellectual property owners. Litigation finance doesn’t present a taxation loophole to close. It’s a process that allows plaintiffs with strong claims—and limited resources—to make it to the courthouse steps. In the IP world, where the costs of litigation can eclipse the means of most inventors, startups, and universities, non-recourse litigation funding often is the only way to level the playing field. The investment risks for funders are high; the returns shouldn’t be penalized. The right policy response isn’t punitive taxation or blanket disclosure of sensitive funding terms, but acceptance of funding as a necessary tool and tailored transparency under the court’s supervision, so that financial disparity doesn’t become a tactical weapon.  The goal is simple: Keep the courthouse doors open while maintaining fairness and integrity in the adversarial system.
Statue of Lady Justice holding scales and sword, blindfolded.
By W. Tyler Perry October 23, 2025
It feels like every couple of weeks an article appears lamenting the rise of litigation finance as the death of capitalism and the birth of something monstrous. The most recent chorus began over the summer when the CEO of Chubb called litigation finance “ a hidden tax on society ” in the editorial pages of the Wall Street Journal. A month later, the CEO of The Hartford grieved on an investor call that litigation finance has “turned our judicial system into a gambling system.” And just last month, the American Property Casualty Insurance Association ’s Senior Vice President of Federal Government Relations exclaimed: “Too many baseless claims, filed by lawyers motivated by profit are clogging our legal system with unnecessary lawsuits, increasing costs and delaying swift resolution of genuine legal claims.”  As someone who has been a big firm defense lawyer, a small firm plaintiff lawyer, and now a litigation funder, I can confidently say that these arguments fundamentally misunderstand litigation finance and its incentives, while simultaneously conflating the interests of large repeat defendants with those of society writ large.