Chicago Procurement Fails

March 19, 2025

Mayor Brandon Johnson’s hand-picked Chief Procurement Officer, Sharla Roberts, asking for a three percent across-the-board supplier price reduction is more than a fiscal embarrassment -- it’s procurement malpractice

In recent quarters, Mayor Brandon Johnson’s Chicago has been plagued by procurement leadership failures and gifting scandals, collectively showcasing that the stinking fiscal swamp next to Lake Michigan continues to expand as graft and corruption serve in place of competition and fiscal discipline in awarding contracts to suppliers. 

Drain it you say? Nah, they are filling it. 

If you need to know, yes, we predicted this (as any reasonable party could have after Mayor Johnson took the oath of office). 

Chicago Contrarian previously reported that Chicago’s last Chief Procurement Officer (CPO), Aileen Velazquez, who was eminently qualified for the role, was forced out of her job by the Mayor and replaced by Sharla Roberts, whose primary expertise was in supplier diversity contract gerrymandering before her current CPO role. 

Roberts, unlike her predecessor, lacks established procurement leadership skills as a previous operations executive, does not appear to have deep technology acumen in systems that could save Chicago tens or hundreds of millions of dollars annually (e.g., strategic sourcing/RFX, contract management, fraud prevention, transactional purchasing systems, etc.) and shows no evidence of advanced purchasing skills, such as high-stakes negotiation capability with the city’s biggest suppliers. 

Given this context, it’s hardly surprising that Chicago is again trying to plug fiscal holes — this time by unilaterally asking all vendors to accept a three percent price reduction through a single, bluntly worded email. 

From where I sit as someone who has lived and breathed procurement in his day job for 30 years, this is the equivalent of asking your Uber driver for a discount because “money is tight.”

The poorly written note, sent last week, reads:

"Dear Valued Partner:
In light of the difficult economic times, the City of Chicago (“City”) faces new challenges to reduce its costs and allocate resources in a way that accomplishes more with less ensuring service delivery to its citizens. The City has an obligation to taxpayers to pursue all avenues involving cost cutting measures. Vendors doing business with the City are no exception. Therefore, the City requests a price reduction of minimally 3% off all invoices sent to the City for the next twelve months off any contracts you currently hold as a prime contract with the City.
The City will always seek to do business with vendors that offer the most competitive prices. Via email, no later than within five (5) business days of receiving this letter, please provide written confirmation indicating the price reduction you can provide the City under any contracts you currently hold as a prime contractor with the City. Please indicate your response separately for each contract on which you are a prime contractor. We would appreciate a response even if you are not able to accommodate the request at this time. If you have already received a request from the City to reduce pricing on a particular contract this year, please disregard this request with respect to that contract.
For purposes of this letter, the letter shall be considered received the day it is sent via electronic mail. The City will provide you with a formal amendment to your Contract after receiving your response regarding the price reduction you can offer the City.
Please contact DPS at DPSContracts@cityofchicago.org with your response to this request. The City looks forward to a continued partnership with your company and appreciates your cooperation as we navigate these challenging economic times. Your prompt attention to this matter is appreciated.
Sincerely,
Sharla Roberts
Chief Procurement Officer"

Even Chicago aldermen, typically diplomatic critics, are outraged. Examples from X include:

Alderman Andre Vasquez:

“Asking private contractors who have binding agreements with the city to take a 3% cut in already agreed payment is horribly irresponsible as it further erodes already eroding confidence in government. It is not a precedent the city should set. It’s challenging enough as the contractors aren’t even paid quickly the amounts that they are owed.”

Alderman Ray Lopez:

“What normally is loudly proclaimed in September as ‘year end efficiencies’ is now loudly demanded in springtime, proving @ChicagosMayor & his City Council amigos overcharged taxpayers in order to create another slush fund to cover the impending 2025 budget shortfalls.  The question now: Who is getting the 3% whack next week?”

This fiasco confirms exactly what Chicago Contrarian predicted last year regarding Roberts’ qualifications. To wit, the notion that someone can waltz into a CPO role for a major city without a senior leadership background in all of the procurement (or at least the highly strategic areas) is not just optimistic, it’s downright delusional, especially in Chicago, given the city’s historical procurement fraud issues and current, half-baked technology systems. Unless, of course, you are an alderman or mayor with a vested interest in seeing proper procurement processes never run in the first place because such formalities may toss a kink into your plans for, shall we say, “diverting” things? 

In contrast, as we noted, “To genuinely qualify as Chicago’s CPO, one should have at minimum:

  • Extensive category management experience across multiple areas — IT, SaaS/software, construction, and office products.
  • Experience leading diverse procurement teams (contract specialists, buyers, IT professionals, process owners, risk and fraud management specialists — essentially a Noah’s Ark of procurement talent).
  • A robust understanding of source-to-pay technologies, including spend analytics, supplier onboarding and management, cyber risk assessment, and deep familiarity with platforms like MDF Commerce, Ivalua, Coupa, and SAP Ariba.
  • Proven capability in high-stakes negotiations and change management, including successful large-scale procurement system implementations.
  • Profound insight into public sector-specific procurement issues, including supplier diversity, recruitment, cross-departmental spend visibility, budgeting constraints, and fraud prevention mechanisms.”

This is what happens when you swap out a competent procurement executive for someone whose primary qualification appears to be a commitment to awarding contracts based on wokeness and the social justice oppressed/oppressor binary.

The result? A procurement strategy that makes Fyre Festival planning look competent by comparison.

What Should Have Been Done Instead

Procurement isn’t a game like Fortnite, where you click on construction material and a refuge suddenly appears. 

Instead, purchasing actual savings comes from structured, strategic approaches. 

Here’s what should have happened:

  • Spend Analytics & Benchmarking: Before you start asking for discounts, you need a clear picture of your spending and where you have leverage. This means breaking down costs by category, vendor, and contract, benchmarking against market pricing, and identifying true cost-reduction opportunities.
  • Should-Cost Analysis: No, this isn’t something ChatGPT can whip up in 30 seconds. This requires breaking down services and products into their component costs — labor, materials, overhead — then determining what a reasonable price should be based on industry margins and telling a supplier to hit that number (which is often 10 to 20 percent less than what you’re currently paying in the private sector more in government.)
  • Competitive Sourcing and Reverse Auctions: Want to drive down costs? Instead of begging vendors, create competition. Proper RFX processes, dynamic bidding, and real-time negotiations force vendors to sharpen their pencils without cutting corners. Competitive negotiation savings range from a few percentage points to 30 percent or more.
  • Contract Enforcement and Compliance Reviews: If Chicago actually enforced contract terms — performance SLAs, price indexing clauses, rebate structures — there’d be no need for desperate email blasts. The real savings are in ensuring vendors adhere to their obligations.
  • Supplier Development and Negotiation Playbooks: Long-term, sustainable savings don’t come from issuing ultimatums. They come from partnerships, joint cost-saving initiatives, and structured supplier negotiations. You don’t get savings by saying, “give me three percent.” You get them by understanding supplier constraints and working through creative solutions.

The bottom line

This “please take less money” strategy wouldn’t fly at a high school lemonade stand, let alone in a major city government. Chicago’s approach to procurement is like trying to make America healthy again by removing one ingredient from the 50+ Chick-fil-A sandwich. 

It’s unserious, ineffective, and borderline insulting to vendors who already face slow payments, bureaucratic nightmares, and Kafkaesque compliance rules — not to mention that many weren’t the most competitive suppliers to begin with (meaning their own cost structures probably aren’t exactly lean, either).

If the City of Chicago actually wants to reduce costs, it needs a procurement team with a backbone, a strategy, and a working knowledge of modern sourcing techniques and technology. Otherwise, the only thing that’s going to shrink is the list of vendors willing to do business with the city — well, except for the ones who can donate to Mayor Brandon Johnson’s reelection campaign or GoFundMe for his inevitable criminal defense fund. 

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