Beating the Odds: How Plaintiffs Win Against Powerful Defendants

Civil litigation against powerful defendants is often an uneven fight. Wealth buys top-tier lawyers, endless motion practice, and the ability to drag cases out until plaintiffs lose hope or resources. For survivors of sexual assault, trafficking, or harassment, the imbalance is even sharper.

And yet, sometimes plaintiffs win.

In Rubin v. Lawson, women who accused former Wall Street trader Howard Rubin of sex trafficking did just that. A Brooklyn jury awarded them millions, later enhanced with attorney fees to over $8.7 million. They prevailed despite Rubin’s resources, reputation, and aggressive defense.

Their victory is part of a larger pattern. Plaintiffs have beaten the odds before — against Harvey Weinstein, Bill Cosby, corporate giants, and hostile institutions. Their stories show that powerful defendants can be held accountable when strategy, persistence, and evidence align.

1. The Prefiling Stage: Building a Case Before Filing

The most important work often happens before the complaint is filed. Plaintiffs’ attorneys know they must anticipate defenses and gather enough evidence to survive the inevitable motion to dismiss.

In Rubin’s Case

• NDAs: Plaintiffs anticipated Rubin’s reliance on nondisclosure agreements. They argued from the start that contracts cannot excuse trafficking or intentional harm.
• Evidence: Travel receipts, medical notes, and messages were collected to provide a foundation before discovery.
• Credibility Prep: Lawyers worked with clients to ensure consistency on the core narrative, knowing minor discrepancies would be attacked.

In Weinstein’s Civil Suits

• Survivors knew NDAs and settlements would be used against them. Their lawyers emphasized public policy — the same principle Rubin’s accusers used.
• Pre-filing coordination with prosecutors and journalists also built momentum, making dismissal less likely.

The Lesson

Plaintiffs win the prefiling stage by treating litigation as a chess match, not a coin flip. They anticipate the defendant’s opening move and position themselves to counter it.

2. Surviving Motions to Dismiss: The First Gauntlet

Powerful defendants almost always move to dismiss. The goal: knock out claims before discovery, when their secrets are still safe.

Rubin

Rubin’s lawyers argued that NDAs barred the claims and that inconsistencies undermined plausibility. Judge Brian Cogan disagreed, citing public policy limits. The case lived.

Weinstein

Weinstein’s teams argued statute of limitations and contract waivers. Courts repeatedly refused to extinguish claims wholesale, recognizing the weight of public policy.

Bill Cosby (Defamation suits by accusers)

Cosby tried to dismiss defamation claims by framing them as protected speech. Several courts allowed the suits to proceed, ruling that calling women “liars” could be defamatory.

The Lesson

Getting past dismissal is survival itself. Once discovery opens, defendants lose control over the narrative.

3. Discovery: Corroborating Testimony

In sexual misconduct cases, discovery is brutal but essential. Plaintiffs’ private lives are scoured — but so are defendants’.

Rubin

Discovery yielded:

• Payment records tying cash to encounters.
• Medical notes consistent with injuries.
• NDAs stored in Rubin’s safe, confirming systemic use.

Weinstein

Discovery confirmed corporate complicity: Miramax and Disney executives knew of settlements, showing institutional enabling.

Cosby

Plaintiffs unearthed deposition transcripts in which Cosby admitted giving women drugs before sex — evidence that turned civil discovery into criminal peril.

The Lesson

Discovery is where allegations meet receipts. Credibility becomes harder to attack when documents, transfers, or prior statements align with testimony.

4. Trial Strategy: Simplifying the Story

Trials against powerful defendants are credibility contests. Plaintiffs win by keeping the story clear, consistent, and human.

Rubin

• Consistency across witnesses mattered more than exact dates. Judge Cogan reminded jurors: “Credibility does not require perfection.”
• The dungeon as stage: Multiple witnesses described the same physical space, anchoring testimony in concrete imagery.
• Control narrative: NDAs, cash, and coercion framed encounters as trafficking, not BDSM.

Weinstein

• Survivors emphasized pattern: multiple women describing similar methods, reinforcing each other’s credibility.
• Prosecutors and plaintiffs linked corporate silence to systemic abuse.

Cosby

• Civil plaintiffs leaned on Cosby’s own words, extracted in prior depositions, to collapse the “he said/she said” dynamic.

The Lesson

The best trial strategies strip complexity. Plaintiffs succeed when they frame the case as pattern + corroboration + control.

5. Verdict and Beyond

Rubin’s jury awarded $3.85 million, later increased with attorney fees to more than $8.7 million. For plaintiffs, the verdict meant validation — but also exposure. Their reputations were scrutinized, their privacy diminished. Yet they walked away with accountability.

Weinstein’s accusers won verdicts and settlements, though many also endured reputational attacks.
Cosby’s plaintiffs won damages in civil court, even as his criminal case ricocheted through appeals.

In each case, the verdicts mattered symbolically as much as financially.

6. Why Plaintiffs Win Despite the Odds

Looking across Rubin, Weinstein, Cosby, and others, a few themes emerge:

1. Public policy overrides paperwork. NDAs and waivers don’t save defendants.
2. Corroboration is king. Receipts, medical notes, and prior statements turn stories into evidence.
3. Patterns persuade. Multiple witnesses describing similar conduct outweigh minor inconsistencies.
4. Persistence pays. Wealthy defendants weaponize delay. Plaintiffs who hold on — emotionally and financially — increase their chances of prevailing.

7. The Costs of Winning

Winning is not without cost. Plaintiffs sacrifice:

• Privacy: Therapy, medical, and sexual histories become public.
• Reputation: Defense lawyers and media amplify inconsistencies.
• Time: Cases drag on for years, draining emotional reserves.

Rubin’s plaintiffs knew this going in. They chose exposure over silence — and won.

8. Reader FAQ

Q: Why don’t NDAs protect powerful defendants?
A: Courts void agreements that excuse abuse or trafficking as against public policy.

Q: How do plaintiffs prove credibility?
A: By corroborating stories with documents, medical records, or consistency across multiple witnesses.

Q: Do wealthy defendants always settle?
A: Often, but not always. Rubin fought to trial. Weinstein settled many cases but went to trial on others. Cosby fought, lost, and faced both civil and criminal consequences.

9. The Larger Lesson

Plaintiffs suing powerful figures face staggering odds: wealth, reputation, and legal firepower stacked against them. Yet victories like Rubin’s show those odds are not insurmountable.

The formula isn’t simple, but it is clear: anticipate defenses, survive dismissal, corroborate testimony, simplify the story, and persist.

Against all expectations, David sometimes beats Goliath.

Follow Small Matter for longform case studies that show how ordinary plaintiffs take on extraordinary defendants — and sometimes, against all odds, win.