The Cases You Are Supposed
To Lose, But Didn’t

Some disputes look unwinnable before the first serious move is made. The contract favors the other side. Liability has already been determined. The client has already made the mistake. The opponent has more lawyers, more money, better optics, or a business model built around making defendants pay because fighting costs more than settling.

Those facts matter. But they do not dictate the outcome. A dispute is rarely controlled by a single fact. The question is whether there is another variable—timing, economics, collectability, evidentiary weakness, counter-exposure, transaction risk, or simply the other side's need to accomplish something—that matters more.

Some of our most successful matters began as cases that, on paper, appeared impossible to win completely—or where "winning" appeared certain to cost the client substantial money. They did not end that way.

Case Study #1: AI Merger

A terminated employee faced an equity claw back attempt from the CEO amidst a $10M merger with backing from sophisticated white-show lawyers threatening to eliminate his participation in the transaction.

The conventional view of the dispute was badly asymmetric. One individual was challenging a company undergoing a merger, with an army of lawyers on the other side and more than $1 million of his equity hanging in the balance. The company controlled the cap table. It controlled the transaction process. And the closing clock appeared to work against the employee as the merger was set to close in 7 days.

The closing clock turned out to be the opportunity.

A corporate acquisition creates obligations that do not exist in an ordinary employment dispute. Cap-table certainty, ownership disputes, intellectual-property issues, representations to an acquirer, and unresolved litigation can suddenly matter on a timetable measured in days rather than months.

We paired evidence of the employee's continued post-separation services with a draft declaratory-judgment complaint and brought the dispute directly against the transaction timetable.

The relative size of the parties stopped mattering. The relevant question became which side could tolerate uncertainty immediately before closing.

Less than 48 hours before the transaction closed, the company executed documents recognizing all 1,000,000 shares. The threatened $233,000 clawback disappeared. The employee received $1.14 million in merger consideration.

What appeared to be an overwhelming resource disadvantage became a timing advantage.

Case Study #2: In the Wrong In the Clear

On behalf of commercial tenant Applebees who was behind in arrears during the covid pandemic, liability had been determined, and the COVID-era rent arguments being advanced by commercial tenants were repeatedly failing. The landlord sought ongoing rent while the litigation proceeded.

This was not a case where the obvious defense simply needed to be argued better. The obvious defense was losing.

That distinction matters.

Once liability has been established, lawyers can become trapped into fighting the case entirely on the opponent's chosen axis: How much does my client owe?

We changed the axis.

Instead of treating the tenant's rent liability as the end of the analysis, we developed affirmative claims concerning the landlord's own conduct. Those claims created a separate source of exposure and prevented the dispute from remaining a one-directional collection case.

The landlord sought summary judgment and pendente lite rent. It did not get them. The tenant's affirmative claims survived.

The lesson was not that the existing liability disappeared. It was that existing liability did not eliminate the tenant's ability to create a materially different litigation position.

Sometimes the way out of a losing defense is not another defense.

It is offense.

Case Study #3: Accounting For Variables

Multiple creditors were already ahead, reducing the practical value of pursuing the same limited pool of money. Additional litigation threatened to become another sunk cost chasing an uncertain recovery.

A judgment and a recovery are two different things.

That becomes particularly important when a debtor has multiple creditors. Even a strong claim can become commercially worthless if obtaining the judgment requires spending substantial additional money only to arrive behind everyone else looking for the same assets.

The problem therefore was not simply proving entitlement. It was structuring a resolution that made payment more valuable than continued resistance.

The matter involved a small $20K loan but complicated by a host of issues. The matter resolved for $25,000, but the settlement was backed by an escrowed $50,000 confession of judgment under CPLR 3218. The structure changed the consequences of default: compliance preserved the negotiated settlement; default exposed the debtor to a substantially larger judgment without requiring the creditor to restart the dispute from zero.

The apparent weakness—the cost and uncertainty of continuing to pursue collection—was addressed through settlement architecture rather than ignored.

When additional litigation threatens to become sunk cost, the answer is not necessarily to litigate harder. Sometimes it is to make future nonperformance more expensive than performance.

Case Study 4: The Contract Favored Them and the Optics Did Too

The claimant was represented by an institutional law firm, relied on broad contractual language favorable to its position, and could point to aspects of the client's own conduct that made the dispute look worse than the underlying economics justified.

Some cases are difficult because the law is bad. Others are difficult because the documents are bad. The hardest can be those where the contract and the story initially appear to point in the same direction.

The claimant demanded $300,000.

Rather than negotiate from that number, we attacked the assumptions necessary to produce it. The dispute was broken into its component contractual obligations, factual predicates, and damages theories. In a single substantive negotiation, the apparent strength of the headline claim was separated from what the counterparty could actually support.

The $300,000 baseline did not survive.

When litigation followed, the claimant sought "no less than $60,000"—an 80% contraction from its pre-suit demand.

Nothing required us to transform imperfect facts into perfect ones. The task was to identify which facts actually controlled the value of the claim.

Bad optics are not damages. Broad contractual language is not self-executing. And an institutional opponent's opening number is still only an opening number.

Cordova: Paying Was Supposed to Be Cheaper Than Winning

Why it looked doomed: Companies confronted with these claims were routinely paying the demanded fee because refusing could expose them to litigation seeking millions of dollars. The economics themselves were designed to make settlement rational even where the defendant believed the underlying claim was defective.

This is one of the most difficult forms of commercial leverage because it exploits a basic truth about litigation: sometimes it costs more to prove that you owe nothing than simply to pay something.

The plaintiff demanded $15,000.

The obvious economic response was to treat that number as a toll—the price of avoiding a much larger lawsuit and the defense costs that would accompany it.

We refused to accept that framework.

Instead, we subjected the underlying claim to immediate substantive and evidentiary scrutiny and forced the plaintiff to confront the weaknesses it would have to carry into actual litigation. The question stopped being whether the company could afford to pay $15,000 and became whether the plaintiff could justify continuing the case when the defendant would not pay simply to make it disappear.

The lawsuit was voluntarily dismissed.

The client paid $0.

The conventional calculation—settlement is cheaper than winning—only works when the other side believes you will accept it.

Never Count Yourself Out of Options

These cases had very little in common factually.

One involved more than $1 million of employee equity immediately before a merger. Another involved a commercial tenant already liable for unpaid rent. Another involved a creditor pursuing money against competing claims. Another involved unfavorable contractual language and difficult client optics. Another involved litigation economics deliberately structured to make paying a nuisance demand cheaper than defending the case.

What they shared was more important:

The obvious battlefield favored the other side.

So the solution was not to fight exclusively on the obvious battlefield.

In Streamr, resource asymmetry became transaction-timing pressure.

In Bay Plaza, a losing defense became affirmative counter-exposure.

In Ghonim, collection uncertainty became payment security.

In Irth, a facially strong contract claim became a damages problem.

In Cordova, the economics of nuisance settlement became a test of whether the plaintiff was actually prepared to litigate the merits.

That is why I am skeptical when someone says a case is "unwinnable."

Sometimes it is. But that conclusion should come only after identifying every variable that can affect the other side's decision—not simply after determining who has the better contract, cleaner facts, larger litigation budget, or stronger opening position.

The objective is not to pretend weaknesses do not exist. It is to determine whether those weaknesses actually control the outcome.

A party can be liable and still possess leverage. A contract can favor the opponent without supporting its damages. A creditor can face collection problems and still engineer payment security. A lone employee can confront an entire corporate legal apparatus and still possess the one thing a billion-dollar transaction cannot tolerate at closing: uncertainty. And a company can face litigation designed to make surrender cheaper than victory and still refuse to pay.

A bad starting position is not the same thing as having no options.

The cases that appear most difficult often require the clearest understanding of what the other side actually needs, what it cannot tolerate, and which variable everyone else has overlooked.

That is where the case changes.