This story was produced by South Side Weekly and the Springboard Project at Type Investigations.
Cook County Sheriff Tom Dart raked in tens of thousands of dollars in campaign cash from more than 100 of his own employees despite facing little competition in his reelection campaign, according to an analysis by South Side Weekly and Type Investigations. Almost all of that money came from a select, although not small, cadre of at-will political employees.
Dart, 64, is seeking a record sixth term in office as head of one of the largest and most powerful agencies in Illinois. With more than 5,000 employees, the Cook County Sheriff’s Office (CCSO) has a broad remit: operating one of the country’s largest single-site jails on Chicago’s West Side, serving orders of protection, carrying out evictions and policing many of the small, unincorporated villages and towns in the county.
It’s legal for Cook County elected officials to collect campaign donations from their employees so long as donations are not solicited during work hours and there are no strings attached—and Dart has long done so. Yet the dollar amount the sheriff has collected this time around from his employees is more than he raised from them in the previous two election cycles combined.
That’s despite the fact that his campaign expenses are relatively modest, as he is running against one third-party candidate in November—Libertarian Brad Sandefur. In 2022, Dart defeated Sandefur and Republican Lupe Aguirre in the general election. He ran unopposed in the general election and in the Democratic primary in 2018.
Dart’s campaign committee, Friends of Dart, has raised more than $315,000 during the current campaign cycle, and as of September 30 had more than $445,000 in cash on hand. Though the sheriff is expected to cruise to reelection, the accumulation of funds may speak to his long-rumored political ambitions for a different office—possibly Cook County Board President in 2030 or Chicago mayor in 2031. Historically, candidates have raised upward of $600,000 in competitive bids for those offices.
In all, 119 employees contributed more than $71,000 to Dart’s campaign fund from November 2022 to June 2026, nearly a third of his total dollars collected from individuals. The share of donations from the sheriff’s employees have markedly increased over the last three election cycles, rising from about 11% of individual contributions in the 2014 cycle to roughly 30% this election.
The analysis is based on publicly available state campaign contribution and county payroll records, as well as sheriff’s office records the Weekly and Type obtained via Freedom of Information Act requests.
“All individuals, including Sheriff’s Office Employees, have the First Amendment right to contribute to political campaigns of their choosing,” said CCSO spokesperson Matt Walberg in a written statement.
Burt Odelson, the lawyer for Friends of Dart, said he couldn’t explain the increase in employee donations during this uncompetitive election cycle. “The committee has no insight as to why individuals choose to exercise their first amendment right to contribute or not contribute,” he wrote in a statement. “The Sheriff has made it very clear to all employees that any choice they make to contribute money or attend events is totally voluntary and in accordance with their constitutional rights to participate or not.”
But accepting employee donations—which some Cook County elected officials voluntarily foreswear—has long been a controversial practice, most famously in the case of former Cook County Clerk Dorothy Brown, who was dogged by corruption allegations during her two decades in office from 2000 to 2020. It is also reminiscent of infamous Chicago-style patronage politics, rooted in the late-19th and 20th centuries, in which municipal jobs were handed out in exchange for campaign work for the elected bosses.
Good government advocates say accepting employee donations creates the possibility of pay-to-play politics and, in the case of employees who can be hired and fired at will, the practice makes it impossible to discern merit-based career advancement from political patronage.
“Even a public official who’s honest and straightforward is still likely to be influenced to some degree by the fact that somebody made contributions to his campaign,” said Michael Shakman, a lawyer and activist whose 1969 lawsuit kicked off decades of federal court oversight of state, county and municipal offices to root out patronage practices.
Alisa Kaplan, the executive director of Reform Illinois, an organization that tracks candidates’ political donations and spending across the state, put it more bluntly. “As long as this is legal, you’re never going to really know how voluntary these donations are,” she said. “There’s always the risk of pressure, and that’s not right.”
The Cook County Board of Commissioners, helmed by President Toni Preckwinkle, could amend the county’s ethics ordinance to prohibit the practice. Some officials are hesitant to restrict employees’ ability to voluntarily participate in the political process, though one of the county’s 17 commissioners told the Weekly and Type that they would support a ban.
Dart has faced accusations of campaign improprieties in the past. A 2023 lawsuit alleged that senior level officials in the sheriff’s office were coerced into working for Dart’s 2022 reelection campaign. A joint FBI-CCSO task force reportedly investigated those allegations as part of a wide-ranging probe that yielded no criminal charges, according to a separate lawsuit. Dart’s office and his campaign fund denied the allegations. Both lawsuits settled out of court.
The Cook County Independent Inspector General’s Office and Board of Ethics, which oversee compliance with the county’s campaign finance rules, declined to comment, citing confidentiality rules.
The rise of employee giving
Dart’s campaign fundraising has steadily grown since he first ran for office in 2006. And in that time, contributions from sheriff’s office employees and those who appear to be their family members have also been on the rise, peaking this election cycle, the analysis shows. Our analysis runs through June 30 of this year, and is limited to contributions from individual donors; we excluded contributions from businesses, as well as transfers in and in-kind contributions from other campaign committees. We defined family members as people who share a surname and home address with a CCSO employee.
In the run-up to the 2014 election, 41 employees gave Dart over $21,000 out of nearly $197,000 raised from individual contributors. That stayed fairly consistent in the next campaign cycle, when 51 employees contributed just over $20,000. Dart won the Democratic primaries handily in both years and was uncontested in the November general elections.
But CCSO employees started contributing a larger share to Dart’s campaign chest after the 2018 campaign. In his run for a fifth term in office in 2022, Dart raised just over $38,000 from 62 employees, accounting for about 22% of his total individual contributions. This time around, employees make up about 41% of his individual contributors and account for nearly a third of his roughly $234,000 raised from individuals.
In each of those cycles, a large majority of the cash and donors came not from the ranks of the office’s unionized sheriff’s deputies or correctional officers, but from at-will employees whose positions are exempt from the federal court orders that came out of Shakman’s landmark lawsuit concerning political patronage. That means they can be hired or fired for their political affiliations. About a quarter of these so-called Shakman-exempt employees—who often have higher annual salaries, hold supervisory or policy roles, and are charged with major decision-making within the office—have donated to Dart’s campaign during the current cycle.
Among the Weekly and Type’s other findings:
- Illinois election law requires anyone who donates more than $500 to a campaign fund to disclose who their employer is. We found two apparent violations by sheriff’s office employees: then-Merit Board member Brian J. Riordan made a $900 donation in 2016 without disclosing his affiliation, as did current Merit Board member Wade Ingram, who made a $1,032 donation in 2025 while listing himself as retired. Riordan and Ingram did not respond to requests for comment. Odelson, of Friends of Dart, said that even when disclosure is required, the campaign committee “would not always know if individuals were employees of the Sheriff’s Office or not.”
- Across several campaign cycles, another eight employees disclosed that they work for the county but did not specify that they are employed by the sheriff’s office.
- Apparent family members of employees upped their giving in recent years, roughly doubling from around $5,100 and $4,400 in the 2018 and 2022 cycles respectively, to over $10,000 this cycle.
- Altogether, more than 190 employees and their family members have contributed roughly $174,000 to Dart’s campaign fund since November 2010, representing 22% of all the money he’s raised from individuals during that period.
The increase in campaign donations by Dart’s employees and their families is “disturbing” and “undesirable,” said Dick Simpson, an emeritus professor of political science at the University of Illinois, Chicago and a former city alderman.
“They don’t appear to be a violation of Illinois law,” he said, “and that’s partly because Illinois law is really weak.” While Illinois, like many states, only prohibits direct quid pro quos—say, a pay increase in explicit response to a campaign contribution—federal law governing congressional offices bars employees from contributing to their bosses’ campaigns.
As of July, Dart had barely used any of his campaign cash in the run-up to this November election. Instead of spending it on campaign staff or activities, such as mailers, rallies, or speaking events, Dart mostly dipped into it for donations to his preferred charities, including to his old high school, Mt. Carmel; the Chicago Police Department’s memorial fund; and a foundation dedicated to a West suburban girl who was killed in 2011 during a burglary.
Simpson said that while Dart may be building up his campaign fund to run for a different office, he could also be doing so defensively—to protect his current position.
“Political candidates, particularly when they’re [running for] higher offices, like Congress or county offices, want to raise money so that people won’t run against them,” he said. “As an incumbent, he also has name recognition and a record to run on, all of which makes it more difficult to challenge him.”
Dart did not face a Democratic challenger in the March primary, widely viewed as the electoral pivotal contest in a county that votes overwhelmingly blue. The only candidate who will appear on the ballot against Dart is Sandefur, the Libertarian candidate whom Dart defeated by more than 1 million votes in 2022.
Dart’s primary campaign that year was run by a longtime sheriff’s office employee, David Feller, who took a leave of absence from the office to helm the reelection effort. The race was poised to be competitive until Feller successfully challenged the candidacy of Dart’s top Democratic primary opponent using a controversial provision of the state’s landmark criminal justice reform that created stringent eligibility requirements to run for sheriff.
Feller first joined the sheriff’s office in 1995, and he made small consistent donations to his boss’s campaign since Dart was first elected in 2006. By the time he was tapped to run the 2022 campaign, he had contributed $775 over three election cycles. He also held many roles in the sheriff’s office, from legislative affairs coordinator in 2011 to deputy inspector in court services in 2014 and superintendent of the Fugitive Apprehension Unit in 2021.
Feller returned on the county payroll in July 2022, well before the general election that November. He is now employed at the sheriff’s office as a senior advisor in the public policy division. With a salary of roughly $140,000 a year, he is the division’s highest paid employee earning at least $15,000 more than both its director and deputy director.
Feller did not respond to requests for comment.
A politicized workplace
Dart’s last campaign drew scrutiny for possible irregularities. Drake Carpenter and Aracelis Gotay, two former high ranking Cook County jail officials who had been placed on administrative leave, alleged in a retaliation lawsuit that they and dozens of coworkers were pressured by their supervisor David Chiko to do unpaid campaign work for Dart’s 2022 reelection bid, including checking nominating petitions and canvassing. Carpenter and Gotay were subsequently fired.
Chiko had allegedly told them that “the boss” needed their assistance.
“We were volunTOLD to challenge the signatures for [Dart’s] challengers (especially Carmen Gercone),” Carpenter told the Weekly and Type. “We had to use our own time off and worked on that instead.”
At least 30 sheriff’s office employees participated in helping Friends of Dart with petition challenges in 2022, the Chicago Sun-Times reported. Chiko later allegedly expressed “the boss[’s]” gratitude for their work.
The case was settled in 2025. Carpenter and Gotay each received $35,000 from the county and $1,500 from Dart’s campaign. The Sheriff’s Office and Friends of Dart did not admit liability and denied all the allegations contained in the lawsuit. Odelson, the campaign committee’s lawyer, wrote in a statement that the lawsuit was resolved for “nuisance value.”
In interviews, other former Shakman-exempt employees described an office culture that is highly politicized.
“Once you get to a certain rank, you are strongly encouraged—because they know that they cannot force you—but they strongly encourage you to support either a fundraiser that he has or some kind of special event,” said Robin Baker, who worked as a lieutenant in the Markham courthouse in the south suburbs from 1994 until 2018. “That was normal.”
Baker said the practice predated Dart. She said she was approached by supervisors while at work, starting about a year before the elections in 2006, 2010, and 2014, and asked if she wanted to buy a ticket.
Gotay said she was also pressured to buy tickets online to Dart fundraisers at the Oak Park Country Club and Connie’s Pizza in 2021 and early 2022 by high-ranking sheriff’s office officials.
“It was something you really couldn’t say no to,” she said.
Cook County ordinance prohibits employees from soliciting donations or campaigning on county property or while on the clock.
Walberg, the CCSO spokesperson, and Odelson, of Friends of Dart, denied that any employees have ever been pressured to donate to Dart’s political campaigns.
“Any employee who feels they have been pressured or encouraged to donate to the Sheriff’s campaign should file a complaint with the Director of Compliance, as the Sheriff’s Office policy dictates,” wrote Walberg.
Mark Wolfe, a former lieutenant in the electronic monitoring division who retired in 2024, said that when he and his colleagues purchased tickets to a fundraiser, they did so expecting “to get something in return.”
“Everything about the department is political, whether they want to admit it or not,” he said.
Wolfe said he bought a ticket for at least $100 to a fundraiser in 2009, hoping it would help smooth the way for his promotion to sergeant. Following the 2010 election, several other sheriff’s deputies who made donations and were up for promotion received theirs, while he didn’t, Wolfe said. Upset, he filed a complaint with the Office of Professional Review (OPR), the sheriff’s internal affairs department, alleging that the sheriff’s office unfairly took into account campaign contributions when it came to promotion decisions. OPR did not end up taking action in response to the complaint, according to Wolfe, who said he no longer has access to those records. The sheriff’s office confirmed Wolfe made a formal complaint in 2011 but said it could not provide a copy because “these records are no longer in existence.” The Weekly and Type were thus unable to verify its contents.
Odelson said it is “flat out wrong” for employees to expect workplace benefits in return for contributing or participating in Dart’s political campaigns.
“We cannot be responsible for the mistaken beliefs of a few employees,” he wrote.
Possibilities for reform
Infamous for a culture of rampant political corruption, patronage is nothing new in Illinois. But reformers have sought to stamp it out by various means, including legislation establishing independent inspectors general and lawsuits that led to court-ordered, merit-based employment plans.
While the Shakman lawsuit, for one, helped put in place protections that would “minimize the likelihood of a return to wholesale patronage practices,” Michael Shakman said he never expected that “we could absolutely eliminate all vestiges of a system that had been in place since the 19th century.”
Dart’s office came under Shakman oversight in 2008 and, in December 2010, was the first office a federal judge deemed compliant. Decree oversight was lifted. As part of that process, the sheriff’s office was forced to adopt an employment plan and other procedures whose primary purpose is to prohibit unlawful political discrimination and political contacts.
“[Dart] met those requirements,” Shakman said. “But of course, once the court orders no longer applied to him and he was free to go about his business, I have no idea of what he’s done and don’t have any current information.”
The following year, Dart hired his office’s court-appointed Shakman monitor, Helen Burke, as probationary director of administration. Since then, records show, she’s made donations to Dart’s campaign fund totaling more than $1,900 and her annual salary has climbed from $120,000 in 2013 to roughly $200,000 as chief legal officer today, putting her among the highest paid individuals in the office.
Burke did not respond to requests for comment.
Also since the end of Shakman oversight, Dart has almost doubled the ranks of his office’s Shakman-exempt employees, whom he can hire and fire at will, from 172 employees in 2011 to 339 this year. These are the employees who are increasingly fueling his campaigns.
Ethics oversight in Cook County primarily falls to the Office of the Independent Inspector General and the Board of Ethics. Both agencies typically act in response to complaints from the public and have the power to assess fines or take other action if they find wrongdoing. Neither appears to have previously investigated Dart or his campaign committee, according to a review of publicly available reports.
The Board of Ethics also hosts a voluntary annual ethics training, which the sheriff’s office attended this year, as well as in 2022 and 2025.
In the early 2000s, former Gov. George Ryan, who was ultimately convicted on federal corruption charges, proposed a law banning employees of statewide offices from contributing to their boss’ campaigns, but it never passed.
Several Cook County elected officials have nevertheless voluntarily pledged in recent years not to accept employee contributions. That includes Preckwinkle, Cook County Commissioners Scott Britton (14th) and Bridget Degnen (12th), outgoing Assessor Fritz Kaegi, and former State’s Attorney Kim Foxx, who served in that role from 2016 to 2024.
“I didn’t want anybody who worked for me to feel that anything that they had achieved by way of promotion was because they had contributed to my campaign,” Foxx said. “Nor did I want people who did not contribute to look around and say, ‘Aha, that’s why it happened.’”
Kaplan, of Reform Illinois, said banning the practice would be better for government functioning.
“It’s not in the public interest for public offices to be staffed by people who are there because they pony up the right amount of money and toe the party line,” she said. “We want people who are there because of their merit and their ability, not because they curry favor with the bosses.”
November 2026 Cook County judicial election guide
Editor’s note: One of the authors of this article, Harley Pomper, filed a First Amendment lawsuit against the Cook County Sheriff’s Office in 2024. The case was settled in 2025.
Ethan Corey contributed data analysis to this investigation.
This article was supported in part by a grant from the Fund for Investigative Journalism.
A note on methodology:
The Weekly and Type matched contributions reported by Dart’s campaign to the Illinois State Board of Elections with Cook County payroll data to identify political donations made by CCSO employees. We also cross-referenced annual rosters of Shakman-exempt employees dating back to 2010 that we obtained using Freedom of Information Act requests to identify political contributions made by exempt employees. A fuzzy matching algorithm accounted for minor variations in name spellings, such as the presence or absence of middle initials and the use of common nicknames, such as “Ricky” for “Richard” or “Bill” for “William.” Though we manually reviewed matches to identify false positives, it is not possible to confirm any individual match with 100% accuracy. Total contribution amounts and counts are best estimates, not exact figures. We identified contributions made by family members of CCSO employees by matching individuals who shared both surnames and home addresses with CCSO employees; this means that we may not have identified all family-member contributions.
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