Cook County’s Untouchable Sheriff: How Power, Politics, and Media Collide Inside Cook County

A System Built to Protect Itself

Cook County’s jail runs on political insulation - a director-heavy hierarchy, a message-managed press shop, and a contempt system that can jail a man for years without conviction.

Inside Cook County Jail, silence is currency. The moment an officer questions corruption, they stop belonging to the system - they become its enemy. Retaliation rarely arrives as open warfare. It comes quietly: a forced transfer, a write-up, or a sudden “investigation” launched by the very officials an officer dared to challenge.

For nearly two decades, Sheriff Tom Dart has cultivated a public image as a reformer — a self-styled humanitarian presiding over one of America’s largest jail systems. But inside Cook County, his administration resembles a political machine more than a law-enforcement agency. Around him stands a network of journalists-turned-directors, political insiders, and loyal appointees. Transparency gives way to control. Dissent draws discipline. Accountability, at best, struggles to breathe.

The Media Shield

In Cook County, image is protection. Tom Dart’s most powerful defense has never been legal - it has been narrative. Over time, he built a communications arm staffed by journalists, producers, and media insiders whose careers once depended on telling Chicago’s stories - now re-tasked to control his own.

Sophia Ansari, once a reporter for ABC 7, now serves as the Sheriff’s Public Information Officer and Director of Communications. Once the journalist calling for statements from law enforcement, she now crafts them - shaping how the public perceives every controversy surrounding Cook County Jail.

Matthew Walberg, formerly a Chicago Tribune reporter covering courts and crime, left journalism to become Tom Dart’s Executive Director and chief spokesman. His understanding of newsroom operations gives Dart’s administration a crucial advantage -the ability to anticipate questions, frame narratives, and steer coverage from the inside out.

Shereen Mohammad, once a producer for WBBM News radio, also crossed the line between media and message. As one of the Sheriff’s Public Information Officers, she now operates within a department that decides which stories reach the light of day - and which quietly disappear.

Patrick Flannery, son of FOX 32 political reporter Mike Flannery, brings familial press ties into the Sheriff’s chain of command as Director of Community Engagement. His role links the Sheriff’s Office to community events and newsrooms, blending civic outreach with media access in a way that secures favorable coverage and stifles criticism.

Roe Conn, one of Chicago’s best-known radio hosts, was hired into a director-level role focused on crime analytics - a post with public visibility but vague operational definition. His name recognition and celebrity lend legitimacy to the administration’s narrative, signaling that even media figures trust and work under Dart.

Together, these hires form a media shield - a revolving door between the newsroom and the administration that ensures the Sheriff’s Office speaks through friendly voices.

When journalists become directors, the watchdog becomes part of the machine. When storytellers work for the subject, who tells the story?

That is why crisis after crisis passes without reckoning. The press can no longer fully hold accountable the institution that now employs many of its own.

The Political Web

Tom Dart’s second shield is political - and no less deliberate. His director roster mirrors Cook County’s power grid: less about function, more about favor.

Deborah Mell, former 33rd Ward alderman, daughter of longtime power broker Ald. Richard Mell, and sister-in-law of ex-Governor Rod Blagojevich, now holds a director-level post as Community Recovery Specialist. Her presence brings the weight of one of Chicago’s most entrenched political families into the Sheriff’s orbit.

Jason Hernandez, her former Chief of Staff during her City Council tenure, followed soon after into a director-level position within Dart’s administration - an example of loyalty translating into security.

Lonnie Hollis, once a correctional sergeant respected among staff and union circles, was elevated to a director-level management position. The promotion neutralized a union-connected figure, turning a potential critic into part of Dart’s managerial class.

Peggy Gustafson, sister to a longtime Sheriff’s lieutenant, now serves as Director of the Compliance Office - a department responsible for oversight and integrity. Her placement solidifies familial loyalty within a role meant to police ethical conduct.

Soo Choi, former senior HR official for the City of Chicago, was appointed Executive Director of Human Resources, importing City Hall’s political networks directly into the Sheriff’s infrastructure.

Through a public-records request in 2025, the Sheriff’s Office confirmed at least 100 individuals hold “Director” or “Executive Director” titles. Yet multiple known figures - including Roe Conn - are absent from the list, implying that the actual count is higher.

For comparison:

   •    Virginia DOC: 14 Division Directors

   •    Utah DOC:  11 Directors

   •    Maryland DPSCS:  9 Directors

   •    Federal BOP: 1 Director, 1 Deputy, 7 Assistant Directors

Cook County Jail, a single county facility, has more directors than some entire state and federal correctional systems combined. This is not management — it is insulation: a labyrinth of patronage designed to shield those at the top.

This structure intersects with one of the jail’s most dangerous practices: cross-watching, rebranded internally as “dual assignment” — the unsafe and contested as unlawful in ILRB proceedings practice of forcing a single officer to monitor multiple housing tiers.

In ILRB Case No. L-CA-21-033 (Janda & Bollinger v. Cook County), the Illinois Labor Relations Board reaffirmed that officers have the right to refuse such unsafe assignments. Yet retaliation persists. Officers who decline dual assignments face write-ups, threats of being fired, forced reassignments, and professional isolation.

Short staffing has made cross-watching the norm, not the exception. Officers are routinely mandated for double shifts - often 16 hours straight - with little notice. Those who refuse are disciplined for “insubordination,” while those who comply risk exhaustion, mistakes, and injury.

It has become a lose-lose equation: work beyond human limits, or face punishment for protecting your safety. Many officers quietly say it feels as if this administration despises its own workforce - placing them in impossible positions to fail, then punishing them for doing so.

The Administrative Wall

The Sheriff’s most effective weapon isn’t force - it’s bureaucracy.

Departments intended to safeguard fairness - Human Resources, the Compliance Office, and the Office of Professional Review (OPR) - have become defensive walls rather than guardians of integrity.

Human Resources, under Executive Director Soo Choi, now functions as a control mechanism. Instead of protecting employees, HR frequently recasts legitimate safety concerns as behavioral issues.

The Compliance Office, led by Peggy Gustafson, nominally exists to ensure ethical adherence and lawful operations. In practice, it functions as a buffer - intercepting internal complaints, slowing investigations, and ensuring controversies rarely escape into public record.

The Office of Professional Review (OPR), supposed to be the watchdog of misconduct, often mirrors the very structure it was built to restrain. Whistleblower complaints frequently circle back to the complainant, transforming victims into defendants.

Together, these three departments form a seamless administrative wall that keeps power intact and shields leadership from accountability.

In Tom Dart’s Cook County Jail, transparency is optional - but silence is policy.

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The Whistleblower’s Punishment

In early 2025, one veteran correctional officer cited PREA Standard 115.13(a) — a federal rule requiring adequate staffing and supervision to protect detainees from abuse - as part of a formal complaint over unsafe conditions and dual assignments.

PREA (the Prison Rape Elimination Act of 2003, 42 U.S.C. §§ 15601–15609) applies to all local jails, including Cook County, and mandates staffing levels, supervision standards, and gender-sensitive monitoring protocols.

“Each facility shall develop, document, and make its best efforts to comply on a regular basis with a staffing plan that provides for adequate levels of staffing and, where applicable, video monitoring, to protect inmates against sexual abuse.” - 28 C.F.R. § 115.13(a)

The officer also referenced the U.S. Department of Justice’s 2008 Cook County Jail Findings Report, which documented chronic understaffing, delayed medical response, and patterns of unsafe supervision — deficiencies that federal investigators tied directly to detainee harm.

The following day, while home and off duty, the officer received a phone call from an Executive Director attempting to force him to submit his job bid immediately - without information, notice, or preparation. It was a transparent act of coercion, the kind of bureaucratic retaliation meant to send a message: questioning the system carries consequences.

When the officer filed a complaint with OPR, the focus of the investigation turned on him instead of the department. He had violated no rule - only the unwritten one: do not challenge power.

Public records and investigative outlets such as South Side Weekly and Unicorn Riot have documented similar reprisals - employees punished for exposing internal misconduct or questioning orders.

In South Side Weekly’s 2021 investigation, “Lawsuit Accuses Sheriff of Retaliation Over Fraud Investigation,” a county employee alleged that after uncovering fraud within the Electronic Monitoring Division, she was removed from her position and targeted by internal investigators rather than protected by them. The lawsuit claimed that the Sheriff’s administration retaliated against her for reporting financial misconduct - a pattern echoed by other officers who raised concerns about safety, staffing, and corruption.

Each case fits the same pattern: those who enforce the law find themselves targeted by those who break it.

The Fanady Paradox

Few stories expose Cook County’s intersection of politics, privilege, and punishment as starkly as that of Steve Fanady, a 61-year-old businessman held in Cook County Jail for civil contempt - not a criminal charge.

In 2011, amid his divorce from Pamela Harnack, a Cook County judge valued his estate at $7.3 million and awarded Harnack 120,000 shares of CBOE stock - then worth roughly $2.9 million.

Years later, litigation revealed that roughly one-third of those shares were tied up in an ownership dispute with Jerome Israelov, Fanady’s former business partner. Although the court acknowledged Israelov’s claim, it never amended the decree.

By 2020, with the stock’s value soaring, the court ordered Fanady to produce the 120,000 shares or pay $10 million - a sum reflecting appreciation and related obligations. Fanady argued that he no longer held the stock, and that part of it was not legally his to transfer. The court disagreed, found him in civil contempt, and ordered his detention until he purged the contempt.

He has remained incarcerated for more than three years - for debt he contends he cannot pay, tied to assets he no longer possesses. During that confinement, both of Fanady’s parents died - a loss that renders his civil detention not merely a question of law, but of humanity itself.

The July 31, 2024 circuit court opinion by Judge Michael A. Forti described Fanady’s defense as “woefully deficient” and his testimony as “not credible.” The case itself states:

“Although the Court had always intended to issue a written ruling containing specific findings of fact and conclusions of law, this Court ultimately issued a brief oral opinion.”

Judge Forti elaborated further during the proceeding:

“Rather than waiting for me to issue my opinion that is going to ultimately deny Mr. Fanady’s request for relief, given his lack of evidence, even though I convened a multi-hour hearing on this, why don’t I just memorialize today that judgment because I found his case to be woefully deficient, and I found him [Mr. Fanady] not to be credible.”

The tone of this denial is not only punitive but also deeply personal - insinuating that the decision to deny Steve Fanady’s release was based as much on opinion as on law. What should have been a written ruling containing specific findings of fact and conclusions of law became, instead, an oral rebuke that blurred the line between judicial reasoning and personal disdain.

That phrasing invites an uncomfortable question: in a case orbiting powerful social networks like the Union League Club of Chicago, could proximity itself - not proof - have shaped perception?

Pamela Harnack is the daughter of Don Steger Harnack, a former President of the Union League Club - one of the state’s most influential civic institutions.

There is no evidence of judicial bias - but in a jurisdiction where social and professional circles so frequently overlap, even the appearance of influence matters.

Fanady’s confinement now sits at the crossroads of legality and morality. Under Article I §14 of the Illinois Constitution, “No person shall be imprisoned for debt, unless he refuses to deliver up his estate for the benefit of his creditors.”

After more than three years, the coercive intent of Fanady’s detention has faded; what remains looks indistinguishable from punishment for debt - the very condition the Constitution forbids.

Yet his case receives little coverage, perhaps because the moral dissonance is too sharp: a man held indefinitely for a civil judgment in a jail run by a sheriff who calls himself a reformer.

Questions Cook County Must Answer

·  How many officers must be threatened before the County Board intervenes?

·  How many detainees must die before the Department of Justice returns?

·  How many whistleblowers must be silenced before Cook County admits that its Sheriff answers to no one?

The genius of Tom Dart’s system isn’t how it serves the public - it’s how flawlessly it serves itself.

In the Interest of Transparency

Publishing these salaries is not an act of defiance - it is an act of transparency, a record of how public money concentrates in administrative ranks even as frontline resources collapse.

The following information is drawn directly from Cook County Department of Human Resources payroll data obtained through lawful public record access and verified through the county’s data portal.

It lists director-level and executive-director positions within the Cook County Sheriff’s Office, including titles and base salaries.

Cook County Sheriff’s Office — Director & Executive Director Payroll‍

(All salaries reflect base annual pay as released by the Cook County Department of Human Resources.)

   1.    Ansari, Sophia — Director — $125,663

   2.    Beachem Jr, Don — Executive Director — $159,213

   3.    Bellettiere, Joseph — Executive Director — $150,367

   4.    Bennett, Martin — Executive Director of Emergency Communications — $163,045

   5.    Bock, Heather — Executive Director — $128,519

   6.    Bray, Jason — Director — $87,657

   7.    Carlson, Matthew — Director — $138,133

   8.    Carmody, Kathleen — Executive Director — $138,615

   9.    Carr, Bryan — Director — $114,494

   10.    Chambers, Anne — Executive Director — $132,300

   11.    Chambers, Sean — Executive Director — $129,426

   12.    Chatz, Sherry — Director — $133,929

   13.    Choi, Soo — Executive Director of Human Resources — $159,600

   14.    Cianciarulo, Jason — Assistant Executive Director — $142,083

   15.    Collins, Lasharme — Director — $127,708

   16.    Connelly, Kevin — Executive Director — $159,665

   17.    Cook, Vincent — Fiscal Director, Trust Office — $121,880

   18.    Cornier, John — Director — $117,166

   19.    Danko, Katherine — Director — $121,574

   20.    De Lisa, James — Director of Renew & Swap — $120,243

   21.    Debro, Yolanda — Director — $139,254

   22.    Duignan, Todd — Executive Director — $135,845

   23.    Dukes, Pamela — Director — $95,212

   24.    Dziedzic, John — Director — $128,232

   25.    Ertler, Dawn — Executive Director — $123,899

   26.    Escalante, Christopher — Director — $95,551

   27.    Feliciano, Alexis — Executive Director — $140,700

   28.    Flannery, Patrick — Executive Director — $143,102

   29.    Garza, Lisa — Director of Payroll — $138,268

   30.    Glick, Elisabeth — Director of Compliance IIC Sexual Misconduct — $130,664

   31.    Gonzalez, Cinthya — Director — $94,998

   32.    Gubser, Jane — Executive Director — $165,832

   33.    Gustafson, Peggy — Director of Compliance — $139,231

   34.    Harrington, John — Director — $153,246

   35.    Harris, Eric — Assistant Executive Director — $117,809

   36.    Hatcher, Sharonda — Director — $117,809

   37.    Hedderman, Jacquelyn — Director — $120,750

   38.    Hernandez, Jason — Executive Director — $143,021

   39.    Hill, Gerard — Director — $119,952

   40.    Hollis, Lonnie — Director — $142,081

   41.    Howard, Ronald — Assistant Executive Director — $142,081

   42.    Hunt, Joshua — Director — $131,250

   43.    Iracheta, Paulina — Director — $122,391

   44.    Jakubowski, Scott — Executive Director — $143,647

   45.    Jarlego Penaranda, Jasmin — Director — $107,742

   46.    Kaufmann, Timothy — Director — $127,727

   47.    Kelly, Patrick — Director — $129,640

   48.    Kenzinger, Cyndi — Director of Victim Support Services — $121,880

   49.    Kinsella, Megan — Director of E911 Communications Center — $148,726

   50.    Klinger, Walter — Director of Police — $153,733

   51.    Korso, Daniel — Executive Director — $142,443

   52.    Lake, Maretta — Director — $139,198

   53.    Leachman, Jennifer — Executive Director — $110,604

   54.    Leal, Tammy — Director — $124,530

   55.    Lienhardt, Christopher — Director — $138,131

   56.    Lindsey, Gregory — Director — $109,845

   57.    Luna, Charles — Director — $139,065

   58.    Martinez, Charles — Executive Director — $148,050

   59.    Martinez, Salomon — Assistant Executive Director — $142,081

   60.    McArdle, Jill — Budget Director — $166,473

   61.    McCray, Kia — First Assistant Executive Director — $138,615

   62.    Mell, Deborah — Community Recovery Specialist (Director-level) — $110,421

   63.    Mills, Blair — Director — $117,599

   64.    Mitchell, Tara — First Assistant Executive Director — $138,615

   65.    Moore, Christopher — Director — $138,029

   66.    Morrison, James — Director of Building Management & Construction - $136,891

   67.    Muhammad, Keyuana — Assistant Executive Director of Programs — $142,081

   68.    O’Brien, Joseph — Executive Director — $128,361

   69.    O’Connor, Ashley — Director — $115,999

   70.    Owadowski, Pawel — Executive Director — $153,300

   71.    Pantoja, Patricia — Director — $136,500

   72.    Parks, Tia — Director — $131,250

   73.    Pate, Lashiver — Director of Behavioral Health Programs — $118,880

   74.    Payne, Michele — Director — $143,701

   75.    Pineda, Allan — Executive Director — $107,940

   76.    Porter, Antonio — Director of Programs — $107,742

   77.    Queen, Erica — Assistant Executive Director — $142,081

   78.    Reaney, Colleen — Executive Director — $135,000

   79.    Rentas, Miriam — Director — $140,138

   80.    Rhodes, Valerie — Director — $145,036

   81.    Roman, Geraldo — Director — $111,927

   82.    Romas, Jeannie — Director of Strategy & Policy — $119,300

   83.    Romeo, Christopher — Director — $107,099

   84.    Ruffin-Bonhart, Carmen — Director — $137,197

   85.    Salazar, Kelsey — Assistant Executive Director — $117,809

   86.    Schramm, Kathryn — Director — $100,031

   87.    Schurig II, Larry — Executive Director — $139,231

   88.    Simental, Deborah — Executive Director — $138,249

   89.    Spencer, John — Director — $130,000

   90.    Stokes, Emmily — Director of Employee Relations — $124,999

   91.    Taylor, Joi — Director of Employee Discipline — $121,934

   92.    Walberg, Matthew — Executive Director — $138,615

   93.    Walsh, Hugh — First Assistant Executive Director — $151,168

   94.    Webb, John — Director — $126,764

   95.    Westensee, Jay — Assistant Executive Director — $146,999

   96.    Whiting, Christian — Director — $146,999

   97.    Wilensky, Steven — First Assistant Executive Director — $151,168

   98.    Williams, Parris — Director — $132,488

   99.    Yasin, Abraham — Director — $120,224

   100.    Yoksoulian, Martha — Director — $137,353

Sources (Verified URLs)

1. https://southsideweekly.com/lawsuit-accuses-sheriff-of-retaliation-over-fraud-investigation

2. https://unicornriot.ninja/2025/whistleblowers-account-of-corruption-and-administrative-abuse-within-cook-county-jail

3. https://www.justice.gov/sites/default/files/crt/legacy/2010/12/15/CookCountyJail_findings_7-11-08.pdf

4. https://www.justice.gov/sites/default/files/crt/legacy/2010/12/15/CookCountyJail_agreement_2010.pdf

5. https://www2.illinois.gov/ilrb/decisions/Documents/S-CA-21-033.pdf

6. https://caselaw.findlaw.com/court/il-court-of-appeals/1666684.html

7. https://www.illinoiscourts.gov/files/1151874_R23.pdf/opinion

8. https://ilcourtsaudio.blob.core.windows.net/antilles-resources/resources/4b4bed5d-fa16-4f23-b474-9e958bba434a/In%20re%20Marriage%20of%20Harnack%202021%20IL%20App%20%281st%29%20210014-U.pdf

9. https://ilcourtsaudio.blob.core.windows.net/antilles-resources/resources/fc4b31a9-0db1-4f59-91ae-9c7af230799b/In%20re%20Marriage%20of%20Harnack%2C%202022%20IL%20App%20%281st%29%20210143.pdf

10.  https://www.forbes.com/sites/jayadkisson/2022/07/14/settlor-of-belize-trust-who-would-not-turn-over-cboe-stock-to-ex-wife-sent-to-jail-in-marriage-of-harnack

11.  https://cwbchicago.com/2025/06/man-jailed-3-years-divorce-dispute-appeals-court-rules.html

12.  https://cookcountyrecord.com/stories/654404942-man-stays-in-jail-indefinitely-until-he-pays-ex-wife-10m

13.  https://cookcountysheriffil.gov/wp-content/uploads/2025/05/Cook-County-Sheriffs-Office-Organizational-Chart_4.20.2025.pdf

14.  https://www.commonwealth.virginia.gov/media/governorvirginiagov/secretary-of-the-commonwealth/pdf/org-charts/2023/Department-of-Corrections-Executive-Structure-12012023.pdf

15.  https://corrections.utah.gov/about-us/leadership-team

16.  https://www.dpscs.state.md.us/agencies/DPSCS%20Organizational%20Chart.pdf

17.  https://doc.wa.gov/sites/default/files/2025-02/100-DG001.pdf

18.  https://datacatalog.cookcountyil.gov/browse?category=Finance+%26+Administration

19.  https://ulcc.org/history

20.  https://www.illinoiscourts.gov/judicial-ethics-opinions

21.  https://chicago.suntimes.com/2020/4/10/21215689/tom-dart-cook-county-jail-covid-release-plan

22.  https://abc7chicago.com/tom-dart-cook-county-jail-covid-release-overcrowding/6125368

23.  https://vault.unicornriot.ninja/cook-county-il-jail/Beneath_the_Badge_Corruption_and_Administrative_Abuse_Within_Cook_County_Jail_FINAL.pdf

24.  https://www.injusticewatch.org/2025/january/family-sues-cook-county-sheriff-dart

25.  https://www.injusticewatch.org/2025/december/handcuffed-detainee-dies-beaten-guards

26.  https://www.cookcountyil.gov/sites/default/files/documents/2023-annual-report-medical-examiner.pdf

27.  https://www.justice.gov/crt/file/1348286/download

28.  https://news.wttw.com/2023/06/02/how-chicago-jail-population-dropped-amid-bail-reforms

29.  https://www.law.cornell.edu/cfr/text/28/115.13

30.  https://www.bettergov.org/research-reports

Legal & Editorial Disclaimer

This publication is an independent work of investigative commentary.

The views, analysis, and conclusions expressed herein are solely those of the author, Kade Veritas, and do not represent or imply endorsement by the Cook County Sheriff’s Office or any governmental body.

All information presented is derived from publicly available records, verified court filings, official government documents, and publicly accessible payroll data.

This publication is provided for informational and public-interest purposes under the protections of the First Amendment, the Illinois Whistleblower Act (740 ILCS 174/), and related state and federal laws guaranteeing freedom of information, speech, and press.

© 2025 Kade Veritas. All Rights Reserved.

Published by the Cook County Corrections Coalition (C4) under license.

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