In January 2014, Tonya DeBerry was driving through an unincorporated area of St. Louis County, Missouri, when a police officer pulled her over for having expired license plates.

After discovering that DeBerry, 51, had several outstanding traffic tickets from three jurisdictions, the officer handcuffed her and took her to jail.

To be released, she was told, she would have to pay hundreds of dollars in fines she owed the county, according to her account in a federal lawsuit. But after her family came up with the money, DeBerry wasn’t released from custody. Instead, she was handed over to the municipalities of Ferguson and Jennings, and in each city, she was told she would be released only after she paid a portion of the fines she owed them, according to the lawsuit.

It was as if she were being held for “ransom,” her lawyer would later say.

The Supreme Court ruled almost 50 years ago that a person can’t be jailed for not being able to pay a fine. But like so many people in Missouri, DeBerry had ended up cycling through a succession of jails for that very reason, caught up in what critics have called modern-day “debtors prisons,” used by towns to keep fines flowing into municipal coffers.

“It’s a cat-and-mouse game,” said her daughter, Allison Nelson, who has also spent time in jail for not being able to pay traffic fines.

If DeBerry and her family were exasperated by the heavy-handed collection efforts, they would learn how hard it would be to hold the authorities accountable, especially in Ferguson, even after the killing of Michael Brown later that year drew national attention to the city’s troubled criminal justice system.

The city slowly stopped jailing people for not being able to pay fines as the news media showed the victims were primarily black and the Justice Department made clear that what Ferguson had been doing was wrong. But four years after a federal class-action suit was filed against the city on behalf of thousands of people who claimed they were jailed for their inability to pay fines, the plaintiffs are still waiting for redress.

The city has sought to have the lawsuit dismissed, filing a succession of motions, arguing among other reasons that instead of suing the city, the plaintiffs should be suing the municipal division of the state court. All three of the motions have been denied by the judge, Audrey G. Fleissig, of the U.S. District Court in St. Louis, though one of the rulings was appealed and that took about a year to resolve.

One issue has proved to be particularly frustrating to the plaintiffs: whether the city of Ferguson is even insured for a class action.

In March 2016, the lawyer representing Ferguson sent an email to a representative of the city’s insurer, saying that the scope of the lawsuit had expanded, and that concern about the case “grew” after a similar suit was settled for what was believed to be a “substantial amount of money.”

The five-sentence email concluded with the lawyer, Peter Dunne, of the St. Louis firm Pitzer Snodgrass, saying that legal action may be necessary to resolve the question of whether the city was covered for a class action.

“We believe a DJ [declaratory judgment] suit to determine coverage may be necessary,” Dunne wrote.

Three months later, the insurance trust filed a declaratory judgement suit against Ferguson in St. Louis County Circuit Court, asking a judge to find that the city did not have insurance coverage for class actions.

Dunne’s role was not publicly known until September, when St. Louis Post-Dispatch columnist Tony Messenger reported Ferguson’s allegation that Dunne had violated his duty to the city. The email documenting Dunne’s discussion of a lawsuit with the insurer was first obtained by ProPublica. Dunne, one of the firm’s principals, did not respond to requests for comment. The other principals did not respond to emails or to a call to the firm’s office.

Suggesting legal action involving his own client was a breach of legal ethics, some experts said, and the revelation has only deepened the sense among the plaintiffs and their supporters that the deck is stacked.

“No matter where the citizens of Ferguson go in the legal system, justice is really hard for them to obtain,” said Vincent Southerland, executive director of New York University School of Law’s Center on Race, Inequality and the Law. “It’s another example that we have a legal system that was not built to protect and vindicate the rights of the most vulnerable among us.”

The killing of Brown by a police officer in August 2014 and the unrest that followed thrust Ferguson into the middle of a growing national debate over race and law enforcement. But for black people in Ferguson and the surrounding North County region, racial discrimination had long defined their relationship with the local police and courts.

Even as the rest of the country moved on from Ferguson, the people seeking a judgment against the city found themselves mired in the machinations of an insular legal system and an overburdened insurance carrier.

Ferguson, a city of about 21,000 people, was insured through a cooperative of 25 municipalities called the St. Louis Area Insurance Trust, commonly referred to as SLAIT.

The trust has operated largely out of the public eye. It took the persistence of Messenger, who won a Pulitzer Prize this year for his columns on “debtors prisons” in rural Missouri, to make the trust comply with open government laws.

Messenger said the rural courts ensnared whites, while in Ferguson and elsewhere in North County, it was blacks who were victimized. “But it’s the same concept,” he said. “It’s policing on the poor, it’s jurisdictions that don’t have a tax base anymore looking to the judicial system as a fundraising tool and judges allowing themselves to be tax collectors rather than purveyors of justice.”

The trust hired Dunne to provide Ferguson’s defense of the class-action lawsuit. But his firm, Pitzer Snodgrass, was also providing the trust with legal advice on insurance coverage issues, according to a court filing by Ferguson. That set up what Ferguson said in the filing was a conflict that the city had not been made aware of.

Even if city officials wanted to settle the case, the trust claims in court filings there isn’t coverage and it won’t pay out. The insurance trust’s lawsuit will determine whether there is coverage.

Michael Downey, a law professor at Washington University in St. Louis and an expert on legal ethics, said that unless Dunne had Ferguson’s permission, Dunne should not have talked to the insurer about the possibility of a lawsuit over coverage.

“A breach of the duty of confidentiality basically to encourage a party to take action against your client is a pretty serious violation of the rules,” Downey said.

Even if Dunne thought he was conveying something that the insurer already knew, the exchange was still concerning, Downey said.

The trust, through its lawyer, declined to comment.

Michael Frisch, Georgetown University Law Center’s ethics counsel, said that, were the bar to pursue an investigation, any punishment would not be severe. A reprimand — at most, he said.

“It’s the kind of a thing that would not draw that much of a response from the bar,” Frisch said. “Lawyers tend not to get suspended for things like this.”

New York University law professor Stephen Gillers, who specializes in legal ethics, said that regardless of any punishment, Dunn’s actions are significant.

“It’s a big deal, because clients are entitled to loyalty,” he said. “If you can’t be equally loyal to both clients, then you have a conflict and you have to withdraw entirely or from one or the other client.”

For lawyers hired by insurance companies to represent policyholders, the question of who is the client was for many years unsettled ethical terrain, experts say.

Lawyers can feel a sense of obligation to the insurance companies that hire them — and that can provide a steady stream of business — said William Barker, co-author of “Professional Responsibilities of Insurance Defense Counsel.”

Barker, a Chicago lawyer with the firm Dentons, said that until the 1970s, lawyers hired by insurance companies to represent a policyholder typically thought of the company as their chief client. But a series of court decisions since then established that the lawyer owes undivided loyalty to the policyholder, and that is why the lawyer’s actions in the Ferguson case appear to be troubling, Barker said. “That’s something that the defense lawyer ought not to be doing,” he said. “The lawyer who is handling the defense ought not to be involved, certainly in advising the insurance company on coverage issues.”

Michael-John Voss, a lawyer for the ArchCity Defenders, the civil rights group that brought the lawsuit against Ferguson, expects to case to drag into 2020.

“The relief and the remedy has been a long time coming, and there’s no clear end in sight,” he said. “And it reemphasized to me the way that these larger structures are put in place to avoid accountability and to perpetuate a system of social control.”

ProPublica asked the insurance trust if it had instructed Dunne to act as he did, but the trust’s lawyer said the organization would not answer any of ProPublica’s questions because of the ongoing lawsuits.

The insurance cooperative was created in the 1980s to help small St. Louis-area municipalities share the cost of liability insurance and health care. The arrangement worked for the occasional slip-and-fall claim and other routine municipal litigation. But it has not held up well in the face of payouts to cops injured on duty and for actions by the police and the courts.

Most notably, the trust paid $1.5 million to Brown’s family in 2017 to settle a wrongful death claim against Ferguson. But that was hardly the only big hit in recent years. In 2016, a jury awarded $3 million to the family of Jason Moore, an unarmed 31-year-old man, who died after a Ferguson police officer delivered several shots from a Taser.

A state audit released in February showed the organization’s fund balance dropped to $3.8 million in 2018 from $12.2 million in 2016. Like many insurers, the trust also has its own coverage, known as reinsurance, and it turned to those carriers to help with the Moore verdict. But the companies have told the trust that they won’t cover the judgment in the Moore case because the companies allege the trust improperly notified them of the claim. The trust is suing the companies.

Dunne and his firm are no longer working on the Ferguson case. The firm was disqualified by the judge after it hired a lawyer from the ArchCity Defenders who represented one of the lawsuit’s plaintiffs in court.

De’carlon Seewood, who stepped down in March after three and a half years as Ferguson’s city manager, said resolving the lawsuit will help the community move beyond the abuses and the notoriety that came with them.

“It is important to kind of move forward and show that new face, that better face,” Seewood said this year, before he left Ferguson to become the city manager in Fairburn, Georgia, just outside Atlanta. Jeffrey Blume, Ferguson’s interim city manager, directed questions to the city’s attorney, who declined to answer.

Seewood said the city had hoped the insurance trust would take care of the settlement the way the insurer for the city of Jennings had. But Jennings was in a very different position. Its insurer was Travelers, the country’s sixth-largest property and casualty insurer. By contrast, the insurance trust is a small cooperative with dwindling funds.

“The insurance [trust] looked at the enormity of what’s being asked and they said that’s it’s outside their [coverage] of the city, and so the city finds itself fighting with its insurance company about [coverage],” Seewood said.

According to a memo written by the trust’s claims administrator, the plaintiffs originally asked for $27.5 million but during mediation in April 2016 reduced the demand to $9.5 million. That amount is what the plaintiffs believe, based on the policies, is the total coverage limit of Ferguson’s insurance.

Alexandra Lahav, a professor at the University of Connecticut School of Law and an expert in civil litigation, said a case like this typically would be resolved in about two years and said the insurance dispute was slowing the process.

“This really shouldn’t be a very complicated class action,” Lahav said.

Lisa Soronen, executive director for the State and Local Legal Center, a Washington organization that supports states and local governments in legal disputes that rise to the U.S. Supreme Court, said the dispute between the trust and Ferguson didn’t leave the city with many sound options other than fighting the case mightily.

“As a practical matter, Ferguson’s a really small city that has no money,” she said. “If there’s no insurance coverage and there’s a huge judgement, I don’t know how it would pay.”

John Rappaport, a professor at the University of Chicago Law School who has studied the impact insurance can have on police practices and policies, said insurance trusts have a reputation for being less likely than commercial insurers to settle case involving police officers.

“The risk pools or the trusts, they see themselves as extensions of the cities themselves,” he said. “Their reluctance to settle litigation against the police would seem [to be] a kind of loyalty to their members — their cities.”

Rappaport said commercial insurers often see the issues as purely a matter of dollars and cents.

“Whereas if the city either is in a risk pool or the city represents itself, they see it as more of like a moral issue, like we have to stand up for our officers,” he said.

Even after the Ferguson suit is resolved, litigation in Missouri over “debtors prison” practices won’t be. ArchCity Defenders has lawsuits pending in six other cities, with more in the pipeline stretching beyond North County.

DeBerry, the Ferguson woman who was a named plaintiff in the Ferguson class action, was also a plaintiff in the lawsuit against neighboring Jennings, which settled for $4.8 million less than a year and a half after the suit was filed.

But the suit in Ferguson has dragged on longer than DeBerry could wait.

She died in April 2018.

“And now she will never even get a piece of this justice because she’s no longer here,” said Nelson, her daughter. “That’s sad, that’s really sad. It’s actually pathetic because it should have never come to that. It hurts.”