Darrell Mathis: O-Block Grit and Work Comp

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In this episode, Yvonne and Rafael talk with Darrell Mathis, Director of Workers’ Compensation for the City of Chicago, and explore his work to modernize and manage one of the nation's largest municipal programs. 

Darrell shares his 33-year journey from the private sector to public service, offering candid insights into program reform, transparency, and talking about “paying what we owe.” 

He discusses how Chicago has transformed litigation strategy, reduced claim backlogs, and improved fairness for injured employees, all while supporting first responders facing unimaginable risks. 

City of Chicago is self-insured and works with a TPA to administer claims. With over 33,000 employees and 3,600 open claims, Darrell’s team is setting a new benchmark for municipal excellence in workers’ compensation. This conversation is a must-listen for anyone interested in the intersection of leadership, accountability, service mindset, and compassion in public-sector risk management.

Darrell also opens up about his own health journey and how dedicating himself to the City of Chicago and the work he loves became a key part of his recovery.

Key Takeaways

• How municipal code changes, litigation reform, and payment integrity reshaped Chicago’s comp program.
• Why “paying what we owe” builds trust and accelerates resolution.
• The real challenges of managing 3,600 open claims and a $700M reserve.
• Strategies to motivate and retain adjusters in a high-pressure environment.
• Chicago’s commitment to care for catastrophically injured police and firefighters.
• Darrell’s vision to make Chicago the global gold standard for workers’ compensation programs. 

Darrell mentioned some folks who help him keep the lights on at the City of Chicago Workers' Compensation program: 

• Donald “Taylor” Chittick – Asst. Director
• Tiffany Williams – RTW Project Manager
• Kathleen Heenan – Workers’ Compensation Liaison
• Tomeka Long – Workers’ Compensation Liaison
• Ashley Chen – Admin

Darrell mentions his devotion to faith and service. He is an ordained Deacon at the Progressive Baptist Church. His Pastor is Dr. Charlie E. Dates. As an officer of the Church, he is involved with many aspects of the ministry. Black Boy Lit is an initiative of Progressive Baptist Church and Salem Baptist Church. Dr. Dates is the Pastor of both churches.  

Additionally, he and his wife chair a capital campaign for the church, called DREAM. 

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