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Court battles hit taxpayer wallets

Chicago’s legal strategy on reversed-conviction suits — private attorneys, drawn-out fights — adds millions to costs

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Thomas Sierra was exonerated after spending 22 years in prison on a murder conviction. The city fought his lawsuit for more than six years before agreeing to a $17.5 million settlement. (Brian Cassella/Chicago Tribune)
Thomas Sierra was exonerated after spending 22 years in prison on a murder conviction. The city fought his lawsuit for more than six years before agreeing to a $17.5 million settlement. (Brian Cassella/Chicago Tribune)
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Thomas Sierra spent 22 years in prison on a murder conviction before it was overturned in 2018 — only to face another long legal battle.

Like others who said they were framed by Reynaldo Guevara — a notorious police detective with a long alleged history of fabricated lineups, beatings and coerced confessions — Sierra filed a lawsuit seeking compensation that could help him rebuild his life. But instead of negotiating with Sierra, the city spent more than six years paying a team of private lawyers to challenge nearly every aspect of his case.

In 2023, after years of legal warfare, Sierra’s attorneys offered to settle the lawsuit for $14.7 million. The city refused. Not until a judge was about to force a trial, in early 2025, did the city call off its hired lawyers and agree to a deal. By then, Sierra’s price to walk away had risen to $17.5 million.

The city’s long battle resulted in a worse deal for taxpayers, who also had to shell out more than $3 million in fees for the outside lawyers.

In a recent interview, Sierra told the Tribune he would have been happy to settle his lawsuit for less than half of what the city ultimately agreed to pay — if lawyers had made him an early offer instead of spending so much time and money trying to argue the police had it right all along.

“If they would have came (to me) years ago, man, they would probably save the city way more money, and I would have been on my way,” Sierra said.

The costs of decades of misconduct by Chicago police have grown enormous as the city settles lawsuit after lawsuit using expensive private counsel to handle most of the work. Now a Tribune investigation has provided the most detailed analysis yet of how Chicago’s legal strategy has run up costs, making these misconduct cases more expensive on average for taxpayers than similar legal claims in New York and Los Angeles.

The Tribune found Chicago’s final costs to resolve claims in murder exonerations since 2010 averaged nearly $560,000 for each year the person was wrongfully imprisoned — and nearly $100,000 of that amount went to pay private lawyers. In New York, which has a far-better staffed law department and rarely uses private counsel, the equivalent figure was less than $400,000 per year of incarceration.

In the past decade, as Chicago has come to lead the nation in reversed convictions, City Hall more than doubled how much it’s paying outside lawyers on these cases to more than $20 million a year, the Tribune found.

City records show that more than a dozen lawyers logged more than $250,000 in hours defending reversed-conviction cases last year. That amount exceeds the salary of the Chicago Law Department lawyer who oversees their work. The firm where one former city lawyer is now employed billed taxpayers for more than $600,000 last year for her work on these cases.

While the city argues that its aggressive strategy is aimed at protecting taxpayers, the Tribune found that the longer cases drag on, the larger the settlement amounts. The legal battles allow mayors to postpone financial hits to the city budget but place an even heavier burden on future taxpayers.

The top lawyer for Mayor Brandon Johnson’s administration, Corporation Counsel Mary Richardson-Lowry, declined a Tribune request to be interviewed for this story.

Corporation Counsel Mary Richardson-Lowry speaks during a media availability at City Hall on May 27, 2025. (Antonio Perez/Chicago Tribune)
Mary Richardson-Lowry, head of the Chicago Law Department, acknowledged last fall that the city is relying too much on private attorneys and she is starting to change that. (Antonio Perez/Chicago Tribune)

In written responses to questions, including a statement this month, her department noted that the administration inherited a relatively small staff facing an explosion of reversed-conviction lawsuits. Those lawsuits, it said, can be harder and costlier to defend in Chicago because of Illinois’ laws and a strong police union contract. And it said each case requires legal attention to differing sets of facts that can significantly affect taxpayers’ liability.

“The City owes a fiduciary duty to the taxpayers to examine each case closely and carefully,” the department wrote.

In an earlier Tribune interview last fall, Richardson-Lowry acknowledged the city is spending too much money for outside lawyers and said the administration wants to settle cases earlier and, ultimately, to bring more work in-house to do the job for less money.

“That was a model that was set up decades ago, and we are starting to change that,” said Richardson-Lowry, in her third year on the job.

One sign of a new approach came in the fall, when the administration agreed to pay a collective $90 million to settle scores of cases related to disgraced police Sgt. Ronald Watts. By then the city had already paid $11 million in settlements and $20 million to outside law firms over nine years to defend cases involving Watts, who led a crew of tactical officers accused of framing innocent people who wouldn’t pay bribes.

So far, City Hall has yet to reach a global settlement to resolve the roughly three dozen remaining Guevara cases, with five set for trial in the next 12 months. As of March, the city had already spent nearly $47 million on private lawyers working on Guevara lawsuits, plus roughly $140 million in settlements and verdicts for 14 completed cases.

For their part, private law firms told the Tribune their work is critical in defending the strained city budget against people who may be seeking an undeserved payout. After all, the argument goes, not everyone arrested by a dirty cop or freed from prison is innocent.

One of the city’s top billers, James Sotos, said in a statement that “the free-wheeling reversal of convictions in Cook County” and the lawsuits that often follow pose a threat to Chicago’s municipal finances unlike that seen in any other large American city.

One case, dozens of lawyers

At a routine court hearing seven years ago for one of the Watts lawsuits, so many city-hired private lawyers had crowded into a federal courtroom that a judge wondered how all the attorneys on the case would find seats.

“It’s a small courtroom,” U.S. Magistrate Judge Sheila Finnegan told the group. “And there are so many of you.”

That lawsuit, filed in 2016 by couple Ben Baker and Clarissa Glenn, anchored a group of early cases related to Watts and his crew. To fight the suit, the city hired multiple law firms, which the law department told the Tribune is sometimes necessary to avoid potential conflicts of interest.

Clarissa Glenn and Ben Baker in the law offices of Loevy & Loevy in Chicago, Sept. 15, 2016, after a federal lawsuit was filed against a corrupt crew of Chicago police officers including Sgt. Ronald Watts. (Nancy Stone/ Chicago Tribune).
Chicago settled a lawsuit filed by Ben Baker and Clarissa Glenn, shown in 2016 at the Loevy & Loevy law offices, for $7.5 million after a long fight that cost the city an additional $5.7 million in legal fees. (Nancy Stone/ Chicago Tribune)

One firm would represent the city and three former top department officials named in the lawsuit. The city hired a second firm to represent Watts, as the city was legally responsible for covering legal judgments against him despite his federal prison sentence for shaking down a drug courier. More lawyers would represent another ex-cop who was sent to prison for the same scheme as well as another dozen current and former cops named in the lawsuit.

Eventually, court records show, more than 40 private lawyers from four city-paid firms registered with the federal courts to defend the case.

As the years passed, invoices ebbed and flowed from month to month and firm to firm but rose toward the end as a judge drew closer to forcing a trial. In that last year — like the end of a fireworks show — the lawyers set off a burst of filings and arguments over what evidence and which experts could go in front of a jury.

Then it all became moot when the city settled the case in January 2025 for $7.5 million. By then, the city-hired attorneys had billed for more than $5.7 million in legal fees.

It was one of the highest-billing civil cases the Tribune found in the past decade, with more than 40% of the combined $13.2 million going to private lawyers hired by City Hall.

To be sure, this suit was arguably a test case for the city in litigating cases involving Watts. The $90 million settlement proposed last fall covers roughly 180 lawsuits related to that crew, sparing the city the expense of litigating those claims one by one.

A global settlement in the Guevara litigation would be much more complex, given that many of those exonerees spent decades in prison on murder convictions. By contrast, the victims of Watts and his tactical unit typically were framed for lower-level crimes and served far less time.

Out of roughly 50 Guevara lawsuits filed over the years, 36 remain pending at the Dirksen U.S. Courthouse, with many still in the early stages of litigation.

It could be a long journey. The Tribune’s analysis of civil claims by murder exonerees found the typical lawsuit in Chicago took nearly five years to resolve, compared with less than two years in New York and roughly three years in Los Angeles.

Consider two lawsuits settled last July, one in Chicago and one in Los Angeles County. Both involved men exonerated in murder cases after spending roughly two decades in prison. Both accused cops of framing them; both local governments hired private lawyers to defend the lawsuits.

In LA, the case of Alexander Torres took less than three years before the two sides reached a settlement of $14 million. The private lawyers hired by Los Angeles County billed roughly $720,000 in fees and costs.

But in Chicago, the lawsuit filed by Roberto Almodovar — one of the Guevara cases — took twice as long to settle, with nearly twice as many court filings, resulting in more than $1 million in legal defense invoices. Despite the long fight, the end result was a settlement of $17 million — $3 million more than Los Angeles County paid Torres.

Roberto Almodovar, second right, embraces his daughter Jasmyn Almodovar as the family walks from Cook County Jail after Roberto was released from custody after more than 20 years in prison on April 14, 2017. (Chris Sweda/Chicago Tribune)
Roberto Almodovar, second from right, embraces his daughter Jasmyn in April 2017, when he was released from custody after more than 20 years in prison. He later sued the city. (Chris Sweda/Chicago Tribune)

The Johnson administration declined to respond to specific questions about the Almodovar case or any others. In its statement and other responses, the law department said it’s unfair to compare Chicago to places that operate under different state laws and different federal court rules, in addition to the differences in law department staffing and number of lawsuits.

The department also said federal scheduling delays, the time needed to address complex cases and the often “unrealistic” amounts plaintiffs demand to settle a case before trial can affect how long it takes to reach a resolution.

“Our responsibility is to evaluate each case thoroughly, protect the City’s legal interests, and ensure that settlements reflect both the facts and the law,” the statement said.

Plaintiffs’ lawyers say none of that adequately explains why, in their eyes, the city directs or allows its stable of private lawyers to litigate cases far longer than other cities.

The Chicago law firm Loevy & Loevy, which has represented many Chicago plaintiffs in reversed-conviction cases, happened to also represent Torres in Los Angeles. Loevy attorney Steve Art said the case showed him how a local government can instruct private lawyers to swiftly settle a case when the government is likely to lose at trial.

“In LA, there was a quick effort to assess the facts that does not happen in Chicago,” Art said last fall.

Attorney Steve Art, of Loevy & Loevy, leaves the Dirksen U.S. Courthouse in Chicago after appearing before U.S. District Judge Sarah Ellis on Oct. 20, 2025. (Terrence Antonio James/Chicago Tribune)
Steve Art, an attorney with Loevy & Loevy, represented the plaintiff in a reversed-conviction case in Los Angeles and told the Tribune: “In LA, there was a quick effort to assess the facts that does not happen in Chicago.” (Terrence Antonio James/Chicago Tribune)

In 2024, Loevy & Loevy went so far as to unsuccessfully ask a judge to allow the firm to pitch a settlement deal directly to the City Council.

“There can be no serious dispute that the ‘business as usual’ method of trying to resolve cases by exchanging letters with defense counsel is not working — for the parties, for the court, and for the city itself — and has not worked for a long time,” the motion argued. “Indeed, the only interests that have been conceivably served by the status quo are those of lawyers who may have incentives to protract litigation unnecessarily.”

In court and in statements to the Tribune, the city’s private lawyers have bristled at any suggestion they’re doing anything other than aggressively and ethically representing taxpayers’ best interests. They note that plaintiffs’ firms like Loevy & Loevy have their own incentives to reach settlements and get paid. The law department told the Tribune “one cannot ignore” that plaintiffs’ lawyers sometimes collect a third to 40% of settlements as well as fees.

One defense firm the city frequently hires, Borkan & Scahill, said in a statement to the Tribune that there’s “no doubt” plaintiffs’ lawyers would prefer that the firm “not zealously defend” the city and its taxpayers and for the city to simply cut them a check.

Turning to outside help

The city’s evolution toward hiring outside attorneys for such cases began in the early 1990s as Chicago began facing lawsuits involving former Cmdr. Jon Burge and his “midnight crew” of detectives, repeatedly accused of beating confessions out of suspects, most of them Black, on the South Side.

Chicago had long used outside counsel for other types of legal matters — to the point critics complained that the contracts were thinly disguised political patronage.

Now city leaders were arguing it made sense to hire an outside lawyer to defend Burge because City Hall and Burge were at odds over what had happened and who was to blame. Getting an independent lawyer would help city lawyers avoid a conflict of interest.

Left unsaid: The move let City Hall bring in more firepower to fight claims that could be politically embarrassing to people then in power, including Mayor Richard M. Daley, who had been accused of turning a blind eye to the abuse.

There were other reasons to look outside for help, too. Courts had ruled the city, not individual cops, was on the hook for most payouts involving police misconduct. As the years went by, judges complained that the city’s in-house lawyers had fumbled key casework. And in more recent years, progressive county prosecutor Kim Foxx approved a far higher number of exonerations than her predecessors, leading to more lawsuits the city had to address.

In all, the Tribune identified more than 320 lawsuits in the last decade for which the city hired at least one private firm to defend it in federal court against a wrongful conviction allegation. Typically, the city hired at least two firms, one to defend City Hall and one for the accused cops. But sometimes the city split the cops into groups and hired a third or even a fourth firm to defend each group — such as that early Watts case.

As the number of reversed-conviction lawsuits exploded over the past decade, the city spread most of the work around a dozen firms, who deployed more than 200 attorneys in all plus another 200-plus support staffers.

By 2016 — well into Rahm Emanuel’s second term as mayor — the city was spending roughly $8 million a year on outside lawyers defending reversed-conviction lawsuits in federal court. By last year, under Johnson, the city was spending more than $20 million that way.

The Tribune analysis found little evidence that the strategy has paid off financially, with the city eventually agreeing to settle the vast majority of cases.

In analyzing the cases of murder exonerees who sued, the Tribune found cases typically spawned roughly 300 docket entries and cost taxpayers nearly $900,000 in legal defense fees as the city often took the cases to the verge of trial before agreeing to pay.

Some went longer than the typical five years, like Almodovar’s. His lawyer, Jennifer Bonjean, complained to a judge halfway through the case that she had been pushing for an early settlement but the city hadn’t yet offered a penny.

“As far as I’m concerned, the ball is really in their court to put a real number on the table to make anything move forward,” Bonjean told a judge in 2022.

The case wasn’t settled for another three years, after another $200,000 in city-paid legal fees.

To be sure, the city’s hired attorneys have scored some victories. Even after being exonerated, plaintiffs in these cases must prove that their civil rights were violated, and judges in some cases have dismissed plaintiffs’ lawsuits for lack of evidence. Other times, plaintiffs walked away with far less than they initially demanded.

In one recent case, a former Latin Kings gang member accused Guevara of framing him and sought $40 million. But a jury awarded him just $750,000 after city-paid attorneys argued they should discount the man’s overturned conviction and certificate of innocence because Foxx’s office didn’t thoroughly vet his guilt or innocence.

It’s impossible to measure how often the city’s aggressive strategy pays off for taxpayers, as the city would not release to the Tribune the financial details of early settlement offers made in each case. That made it difficult to compare the amounts plaintiffs’ lawyers sought throughout the life of a case versus what they ended up getting.

What’s left are rare details sometimes included in court records about settlement offers — such as in the Sierra case — and repeated complaints in court from plaintiffs’ attorneys that the city isn’t coming to the table.

The plaintiffs’ lawyers also have complained that delays infuriate their clients, who expect higher payouts as cases drag on. A Tribune analysis of settlement deals confirmed that the amount paid out to murder exonerees per year of incarceration — a standard measurement used to compare cases — grew larger the longer their cases took to settle.

That doesn’t count the cases the city takes to trial and loses. For example, Chicago taxpayers have paid $2.4 million to teams of private lawyers who lost at a trial resolving two related lawsuits. If the judgment stands, it will cost taxpayers $120 million to compensate the two exonerated men.

In another example, a jury decided in 2021 that Eddie Bolden deserved $25 million in a case that, by then, had already cost the city $2.8 million in legal fees over nearly five years.

Since then, the city has continued to fight aspects of the judgment, racking up $1.3 million more in legal fees. Bolden agreed to take less money, $22 million, but the trial judge ruled that Bolden deserves extra compensation to cover the time the case took to get to trial.

U.S. District Judge Steven Seeger wrote in a ruling that the city could have tried to settle but “did not put serious money on the table.”

The Sierra situation

Chicago was a decade into the Burge scandal when Sierra was convicted in 1997 of a fatal shooting in Logan Square.

Someone in a Buick had fired into an Oldsmobile, killing a man in the backseat. The suspect description was vague: a hooded male who had flashed a Spanish Cobras gang sign. The two survivors looked at several hundred photographs of known Cobras but couldn’t ID anyone.

Enter Reynaldo Guevara, a detective who once bragged that he’d spoken to “every gangbanger on the street.” Within the department, he had a reputation for closing the hardest cases by finding witnesses no one else could and getting suspects to quickly confess.

Reynaldo Guevara leaves the Dirksen U.S. Courthouse in Chicago on June 8, 2018. (Terrence Antonio James/Chicago Tribune)
Former Chicago police Detective Reynaldo Guevara, shown leaving the Dirksen U.S. Courthouse in 2018, has been sued numerous times by people he helped put in prison. (Terrence Antonio James/Chicago Tribune)

Guevara, according to his court testimony, recalled seeing a similar Buick at a home of a slain gang member and traced the nickname of a passenger he remembered being in that car to Sierra. Then Guevara said he got both survivors in the Logan Square shooting to identify 19-year-old Sierra as the shooter.

But questions about the detective work soon emerged. Sierra wasn’t actually a member of the Spanish Cobras, and one of the survivors testified at trial he picked Sierra out of a lineup only because that’s who Guevara told him to pick. But the other survivor’s testimony implicated Sierra, and that was enough to send him to prison in an era of limited forensic evidence and a high level of trust in eyewitnesses and police officers.

Years went by, with Sierra sitting in prison, before Guevara’s reputation began to sink. In 2004, during a retrial of one of Guevara’s cases, two supposed crime witnesses said Guevara had coerced them to falsely identify Juan Johnson as the suspect, leading to an acquittal and then a lawsuit in which a jury awarded Johnson $21 million.

That was the first of dozens of cases where a tossed conviction led to a lawsuit in which attorneys argued Guevara framed innocent men by coercing witnesses and, at times, beating false confessions out of the suspects. Before Guevara retired and stopped answering questions in court, one criminal judge called out Guevara’s “bald faced lies” and said the ex-cop had “eliminated the possibility of being considered a credible witness in any proceeding.”

Sierra’s case soon was added to the pipeline after Cook County prosecutors agreed to throw out Sierra’s conviction in January 2018.

Thomas Sierra, center, walks with, from left, Anand Swaminathan, Joshua Tepfer and Steve Art, attorneys with the Exoneration Project, outside of the Leighton Criminal Court Building in Chicago on Jan. 9, 2018. The Cook County State's Attorney's Office announced that it dropped all charges against Sierra for the 1995 murder of Noel Andujar, a case investigated by former Chicago Det. Reynaldo Guevaral. Sierra spent 22 years in prison, always maintaining his innocence. (José M. Osorio/Chicago Tribune)
Thomas Sierra, center, walks away from the Leighton Criminal Court Building with his legal team in January 2018 after Cook County prosecutors dropped charges against him in a 1995 slaying. (José M. Osorio/Chicago Tribune)

Three months later, Sierra filed his lawsuit, alleging he too was innocent and had been framed.

Within weeks, five attorneys from Rock Fusco & Connelly registered with the federal court to represent City Hall.

Then four more attorneys, from Leinenweber Daffada & Sansonetti, to represent Guevara.

And seven more attorneys, from The Sotos Law Firm, to represent other officers named in the lawsuit.

In all, 20 privately paid attorneys eventually signed up in court to work for the defense — with each of their firms billing city taxpayers.

They had been handed a tough case to win.

With Guevara already pleading the Fifth to avoid self-incrimination, the plaintiffs’ attorneys could pepper him with questions in front of a jury that would hear, over and over, his refusal to answer. In one 2018 trial, a jury watched Guevara invoke the Fifth more than 200 times before awarding a $17 million payout to a man, Jacques Rivera, who’d spent a year less time in prison than Sierra.

Even knowing he had a solid case, Sierra told the Tribune he was ready — early on — to settle. He was grateful he’d quickly gotten a job out of prison helping install shower glass but was eager for more financial stability. And he wanted to avoid further reliving the hell of a two-decade imprisonment that he entered as a teen and left in his early 40s.

“I didn’t want to wake up every day thinking about this,” Sierra said.

He said he told his attorneys he’d settle quickly if he could get $10 million, $8 million, even $7 million. But, he said, the city didn’t want to talk about a settlement, just to fight him.

A faster pace in New York

In other places, other city lawyers look to quickly settle such a case. That’s because plaintiffs and their attorneys are often willing to accept a “discount” to avoid years of legal headaches.

New York City — which typically settles cases for less money than Chicago — uses City Hall lawyers to handle its lawsuits, and it also lets its elected comptroller cut deals with exonerees before a lawsuit is filed.

That’s how it was able to compensate two men relatively quickly, and more cheaply, after they were exonerated in a Brooklyn carjacking and murder that shared similarities to Sierra’s case — in both, a swaggering detective had surfaced to solve a seemingly unsolvable crime.

In the Brooklyn case, the detective was Louis Scarcella, who described a series of lucky breaks that led him and his partner to two teenagers whom a survivor could identify. But decades after the teens were convicted, serious questions arose about Scarcella’s methods and the convictions were overturned along with a dozen others.

Retired NYPD Detective Louis Scarcella leaves a Brooklyn courthouse after testifying in the case of Rosean Hargrave who was convicted of a 1991 homicide on Sept. 24, 2014. Hargrave's conviction was vacated by the court in 2015 and in 2018 he was cleared of all charges in the case handled by Scarcella. (Theodore Pariseinne/for the New York Daily News)
Retired New York police Detective Louis Scarcella leaves a Brooklyn courthouse in 2014 after testifying in the case of Rosean Hargrave, one of two men whose murder convictions were overturned after questions arose about Scarcella's methods. (Theodore Pariseinne/for the New York Daily News)

Within roughly a year, New York’s city comptroller cut a deal to pay one of the Brooklyn exonerees $6.7 million for his nearly 24 years in prison, or roughly $280,000 for every year, which is about a third of the rate Chicago taxpayers would eventually pay Sierra.

The other Brooklyn exoneree decided to take his chances in federal court. New York City took the unusual step for that city of hiring outside counsel to represent the ex-detective. Even then, only six total attorneys — from City Hall and the private firm — registered to defend the lawsuit.

The Sierra case had a 1½ year head start on that lawsuit, but the Brooklyn case got to the finish line first. Unlike in Chicago, where the city’s private lawyers argued for years over which records to gather and share with the plaintiffs, court records show that the New York attorneys followed a more streamlined record-sharing process imposed by the judges in that federal court system. They also took advantage of the system’s push for early mediation to help settle such cases.

By Thanksgiving 2020, roughly 15 months in, New York city attorneys cut a deal to settle the second exoneree’s lawsuit for $5.9 million, or roughly $350,000 per year for the nearly 17 years he’d spent in prison.

Combined, the payouts to the two Brooklyn exonerees — covering a collective 40-plus years behind bars — were less than what Chicago would end up paying for Sierra’s 22 years’ imprisonment.

In Chicago, Sierra’s lawsuit was arguably even harder for a local government to defend than the botched Brooklyn homicide case. At least in New York, the lead detective was still willing to testify to defend his past work. Not only was Guevara pleading the Fifth, but so was his partner at the time.

In addition, the passenger in the shot-up car had originally testified at trial, then in a later deposition, that Sierra was the shooter. But he was also no longer willing to testify, pleading the Fifth himself in an era when prosecutors at times threatened to charge recanting witnesses with perjury.

The other main witness at the criminal trial — the driver of the Buick — maintained during 2019 questioning that he still had no idea who shot at the car that night and that Guevara had told him to pick Sierra out of a photo lineup.

Two years later, a criminal appeals court judge called Guevara a “malignant blight on the Chicago Police Department and the judicial system” with a “penchant for manipulating witness identification.”

Sotos, one of the city lawyers on Sierra’s lawsuit, recently told the Tribune that he still believed the city had a shot to win at trial. He said the city could have relied on the car passenger’s earlier testimony tying Sierra to the murder while trying to convince a jury that the driver had falsely recanted out of fear for his safety.

Regardless, Sotos said, his firm took its marching orders from the law department, which continued to push the legal fight.

That fight came at a price. In the case’s early years, during the mayoral administrations of Emanuel and Lori Lightfoot, the private firms collectively racked up bills that averaged $10,000 a week as they worked to gather records, schedule depositions and argue over the scope and timing of both.

In December 2021, Sierra’s lawyers floated an offer for $17 million to settle the case, according to a letter they sent to the city memorializing the deal. The firm said its offer was ignored.

Sierra’s case got one more boost months later when a criminal court judge, in the county courthouse, formally issued him a certificate of innocence — finding it more likely than not that Sierra didn’t commit the murder.

Even then, the city didn’t pursue a settlement.

‘Puppet on a string’

In the fall of 2023, the city agreed to mediation to try to settle the case, records show. That’s when Sierra offered to settle for $14.7 million, which in hindsight would have been a relative bargain for taxpayers. It was also less money than a jury had awarded Rivera months after Sierra filed his lawsuit.

But the city law department, now under Johnson, rejected the offer at the end of mediation. City Hall instead offered only $4.7 million, according to a Loevy & Loevy letter memorializing the exchange.

So the legal fight continued, as did the legal bills to taxpayers. By then, the case had entered a final, arduous pretrial stage called summary judgment.

It’s where any side can argue to a judge that the evidence on a particular issue is such a slam dunk in their favor that it doesn’t need to be put to a jury. Those arguments often are combined with battles over whether one side’s expert witness is truly expert enough to go in front of a jury.

Court records show Sierra’s attorneys asked the city to negotiate a deal to limit this phase of the case so both sides wouldn’t have to “waste considerable resources” on pretrial arguments. But that isn’t what happened.

Over six months, the two sides filed roughly 60 motions totaling nearly 2,700 pages with more than 86,000 pages of exhibits.

During this time, the city-paid law firms’ billing increased, averaging more than $30,000 a week and peaking at $25,000 on one day in early 2024.

Sierra, now 49, said he grew more frustrated with each delay. He’d already lost his 20s and 30s to prison. He never got to watch his daughter grow up. And now he was approaching 50, still with this “black cloud” over his head. He kept having to emotionally gear up for a trial that would dwell on the worst experience of his life, then be told to wait longer.

“Their attorneys are filing things, to prolong for another continuance, for another continuance, for another continuance,” he recalled to the Tribune. “I just felt like a puppet on a string.”

Inevitably, the city’s blazing legal fire finally ran out of fuel. By the end of summer 2024, there was little more to argue about how a trial should proceed; the judge had already set a trial date in January 2025.

Then, as in many other lawsuits like Sierra’s, the city suddenly wanted to settle. The change of heart came shortly after a jury in another reversed-conviction case had awarded $50 million to an exoneree who spent half as much time in prison as Sierra did.

But at this point, Sierra’s attorneys were asking for $17.5 million to walk away. With no more room to maneuver, the city agreed to Sierra’s now-higher demand.

Sotos, the city-paid attorney, defended the timing and amount, noting that the $50 million verdict had changed the city’s risk calculations. But Sotos also maintained the Sierra lawsuit “was far from an indefensible case.”

Sierra begged to differ.

Over the lawsuit’s six-plus years, he’d settled down with his longtime girlfriend, moved onto a steadier factory job, and then run his own small shipping firm. He said he suspected the city knew its case was weak but just wanted to drag it out anyway.

“I’m not trying to sound cocky or arrogant, but what is there more that you can argue or fight when a judge is saying, ‘Hey, here you go. You’re exonerated. We believe you’re not guilty. Here is your certificate of innocence’? What else is there more?”

Moves toward change

In January 2025, the City Council’s finance committee took the final, substantive step to end Sierra’s 30-year journey from arrest to imprisonment to exoneration to compensation.

A law department official gave a five-minute rundown of the case, warning that if the council didn’t take the deal, Sierra could ask a jury for $44 million, plus get another $3 million to $5 million for his attorney fees paid.

Nobody mentioned how more than six years of outsourced legal work had cost the city $3.2 million. Nobody mentioned how the city could have saved $700,000 in legal fees, and nearly $3 million on the settlement payout, if it had taken the deal Sierra had offered in late 2023.

The committee unanimously approved the settlement, which was then OK’d by the full City Council the same week.

In its statement to the Tribune, the law department said that since 2023 it had launched efforts to better assess risk and improve oversight of how lawsuits are handled, with a push toward faster and cheaper resolutions. It estimated the global settlement of the Watts lawsuits had cut a half-billion dollars in potential payouts and $15 million to $25 million in future outside legal fees.

Overall, the city said, the number of pending reversed-conviction cases has dropped from more than 240 to 95 in the past three years. “This administration has made tremendous strides to economically and efficiently resolve reversed-conviction cases,” the city said.

Reducing the city’s prolific use of outside lawyers is a much thornier issue. Several new mayoral administrations have said they would bring such legal work in-house but then didn’t. That was true of Richardson-Lowry’s predecessor, who told the Tribune in 2019 that the scope of outside legal fees at the time was “scandalous.”

Richardson-Lowry’s department has avoided such strong language but said it had gotten the OK to hire a dozen more staff attorneys. That’s still well short of the in-house legal staffing in New York City and Los Angeles, and the law department acknowledged it still needs to rely on outside lawyers.

Thomas Sierra spent 22 years in prison for a 1995 murder before being exonerated and suing the city and Chicago police Det. Reynaldo Guevara. (Brian Cassella/Chicago Tribune)
Thomas Sierra said he would have happily settled his lawsuit for much less than the city ultimately agreed to pay, if he could have avoided a long legal battle. (Brian Cassella/Chicago Tribune)

Sotos’ firm has billed the city more than $35 million in the past decade for work tied to reversed-conviction lawsuits — the most of any firm. He told the Tribune he shares the city’s goal of limiting the work given to his firm and others but for now, outside firms’ legal firepower is needed to defend against an “avalanche” of complex cases.

One person who hopes the city changes its approach: Sierra.

He said he’s a taxpayer, too, and it makes more sense for the city to settle legitimate claims like his faster and cheaper. He figures there are plenty of other guys willing to cut a faster deal and get on with life.

“Like I said, I would have been happy years ago, and it would have probably saved taxpayers like … you and everyone else probably millions of dollars, if they’d have come to the table a long time ago,” he said.

And, to Sierra, it’s also about showing respect to those who lost so many years in trumped-up cases.

“For a person to do that much time for something they didn’t do, and come home and still the city of Chicago’s telling you, ‘No, we’re still gonna fight this, you know, we don’t believe you’ — it’s sad,” Sierra said.