Waukegan Mayor Faces Questions Over Black Business Month Support

WAUKEGAN, Ill. — Waukegan Mayor Sam Cunningham is facing renewed criticism from some community members following the city’s celebration of National Black Business Month, with critics questioning whether the administration’s public support for Black entrepreneurship is reflected in city contracts, spending and hiring.

The City of Waukegan recently highlighted local Black-owned businesses on social media, writing that Black entrepreneurs “shape the identity and economy of Waukegan” and that the city remains committed to celebrating, uplifting and supporting them.

The Waukegan City Council also formally recognized National Black Business Month during its August 3 meeting.

But the city’s messaging has prompted a larger question from critics: What does that support look like financially?

Questions are being raised about how much of Waukegan’s municipal spending ultimately reaches Black-owned businesses, how many Black-owned companies currently hold city contracts, and how Black professionals are represented among appointments and senior positions within city government.

Those are measurable questions — and ones that could provide a clearer picture of whether the city’s public commitment translates into economic opportunity.

Police Chief Appointment Draws Scrutiny

Critics have also pointed toward leadership appointments.

The Waukegan Police Department currently lists Elias Agalianos as police chief, while Craig Neal serves as a deputy chief. Neal remains a senior member of department leadership and heads the Patrol Division.

Some Cunningham critics have questioned why Neal was not selected for the department’s top position.

However, claims circulating online that campaign contributions influenced the appointment have not been independently substantiated and should not be treated as established fact without supporting records.

Stretch’s Dispute Has a Documented Court History

Another business frequently mentioned in criticism of Cunningham is Stretch’s Sports Bar & Grill.

Public court records confirm that Stretch’s became involved in years of litigation after Waukegan Hospitality Group filed an eviction action against the restaurant in 2020.

The Illinois Supreme Court ultimately considered an appellate procedural issue stemming from the case in 2024.

Those records establish that a significant legal dispute occurred involving Stretch’s, but they do not, by themselves, substantiate separate allegations circulating online that Cunningham personally engineered the dispute or sought a financial kickback.

Questions Surrounding City Contracting

The debate comes as Cunningham’s administration publicly emphasizes its support for entrepreneurs.

In May, Cunningham described small businesses as vital to Waukegan’s success and promoted the city’s “Rebuild Waukegan” initiative as an effort to reduce red tape and help entrepreneurs establish and grow businesses.

Critics now want numbers attached to those promises.

Among the questions that could be answered through city purchasing and employment records:

How much money has Waukegan awarded to Black-owned businesses during Cunningham’s current term?

How many Black-owned businesses currently hold contracts with the city?

How does that figure compare with previous administrations?

How many Black employees have been hired or promoted into senior city positions?

Those figures would provide residents with something more meaningful than competing political claims: a measurable record.

Black Business Month Puts Record Under Spotlight

Cunningham made history in 2017 as Waukegan’s first Black mayor. His official city biography also lists recognition from organizations including the Illinois Black Chamber of Commerce and U.S. Minority Contractors Association.

That history makes the current debate particularly significant.

Black Business Month is intended to recognize Black entrepreneurship and the economic challenges Black-owned companies continue to face. For Waukegan residents questioning their local government’s record, however, recognition alone isn’t enough.

The city’s Facebook message says supporting the continued growth and success of Black-owned businesses is “essential to the city’s collective prosperity.”

Now the question for City Hall is whether the numbers tell the same story.

Rather than relying on political accusations from either side, Waukegan residents deserve access to the receipts: contracts, vendor expenditures, hiring figures and procurement data.

If the administration’s record matches its Black Business Month message, those records can demonstrate it.

If it doesn’t, they can demonstrate that too.

Pulse Radio 96.1 | The Beat of Lake County