Who are Raki and Kimberly McGregor? CMS consultant deals questioned before Hill firing
Six days before Charlotte-Mecklenburg Schools board members voted to fire Superintendent Crystal Hill, she sent them a scathing 14-page memo raising concerns about some of their ties to CMS contractors.
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One couple was at the center of the controversy.
Raki and Kimberly McGregor, and their consulting businesses, appeared more than 70 times in Hill’s memo.
Since 2020, the McGregors have received more than $4 million in contracts with CMS and Mecklenburg County. Their work was the centerpiece of Hill’s bombshell memo, which has since ignited multiple state and federal investigations into the district’s financial management.
The McGregors, who have not been accused of wrongdoing, are a well-connected business family whose multiple contracts with CMS and relationships with board members triggered concerns for Hill.
But they were largely unknown in Charlotte’s local politics scene until a few years ago, according to multiple political insiders. Their rise in power and prominence unfolded under the radar and in quick pace.
Dan McCorkle, a Mecklenburg County Democrat of 40 years and political strategist, said he never came across the McGregors at events before Raki suddenly emerged as a big player during the 2025 election cycle.
“How did he get access that quick?” McCorkle told The Charlotte Observer. “Why as Democrats have we let this one person become so powerful?”
The McGregors have not addressed media questions surrounding the contracts in recent weeks. They did not respond to an interview request for this story.
The McGregors both lead consulting firms. Raki previously was a senior vice president of digital equity and community growth at Novant Health before he joined CMS as an executive on loan in 2022.
That same year, Raki formed his consulting company, Qonnect, LLC, focusing on leadership and organizational development. Kimberly’s company, SYDKIMYL Consulting, LLC, formed in 2018 and works on education and tutoring. According to SYDKIMYL’s website, Raki is a consultant, their son Myles is the chief digital and innovations officer and their daughter Sydney is the attendance and data manager.
Kimberly spent 15 years as a CMS counselor across elementary, middle and high schools, according to her website. She was also a college counselor at Central Piedmont Community College.
Kimberly was the Charlotte chapter president of The Links, Incorporated, an international community service organization for Black women, and volunteered on the State Employees’ Credit Union advisory board in Cornelius.
Her consulting company received a $10,000 grant from Beyonce’s charity foundation, BeyGood, in 2023 to offer social-emotional learning opportunities to Mecklenburg County students. That same year, North Carolina Lawyers Weekly named Kimberly among its 50 Most Influential Women alongside government officials, educators and business leaders from companies such as Duke Energy and Wells Fargo.
And in 2025 The KNOW Women named her on its own list of 50 women to know in North Carolina. In an interview for the recognition, Kimberly credited her family as her biggest influence.
“My children were entrepreneurs long before I embarked on my journey, teaching me the value of creativity and courage to forge my own path,” she said. “My husband, with his unwavering encouragement, has been my rock, reminding me that I can achieve anything.”
Records show lapses in required business filings with the North Carolina Secretary of State’s office. The agency dissolved SYDKIMYL twice for failing to file its annual reports, most recently in 2023. The corporation was reinstated both times. Raki’s company, Qonnect, was similarly dissolved this September before being reinstated.
Raki serves as an advisor for his son’s luxury transportation company, Charlotte Immaculate, which claims some of Charlotte’s most prominent business leaders as other advisors, including former Bank of America CEO Hugh McColl and former Ernst & Young managing partner Malcomb Coley.
The Observer asked Coley about his ties to the McGregor family and Charlotte Immaculate. He declined to answer questions and criticized the reporter before hanging up.
“Tell me your parents didn’t invest in your education and waste their money so you could ask asinine questions. I want you to print that,” Coley said. “I’ll put my reputation in the community against yours any day.”
Raki has also held board positions with Charlotte Works, DreamKey Partners, One Charlotte Health Alliance, Young Black Leadership Alliance and the board of trustees at Mary Baldwin University, among other organizations.
He has shared publicly that before he found success in business, he made mistakes in his youth.
Raki dropped out of North Carolina A&T State University as a sophomore, then “stumbled even harder,” he wrote in 2022 op-ed in The Charlotte Observer, describing why he took the leap to serve CMS as an executive on loan. He said he “landed in trouble with the law” while managing fast food restaurants but had his case dismissed under a first offender’s deferral program.
He subsequently started two businesses, installing computer cabling and washing cars for dealerships, before deciding to finish his degree when his mother-in-law offered financial support, he wrote.
“Every child should be afforded the opportunity to pursue their dreams regardless of their background,” he wrote. “They also need to know they can survive a mistake or two along the way. Just like I did.”
Raki worked his way to an executive position at Novant Health and held significant political influence as the chair of the Black Political Caucus of Charlotte-Mecklenburg’s transportation committee.
About half of Democratic primary voters in Charlotte are Black, making the BPC an influential group in local politics and its endorsements among the most coveted.
Multiple Charlotte political figures, who spoke on background due to the sensitivity of the ongoing investigations, told the Observer he wielded his BPC position as a hammer, sometimes cracking down in assertive displays of power.
In one instance, McGregor pressured the City Council into revoking support for the controversial Interstate 77 South toll lanes project at the threat of losing the caucus’ endorsement, according to multiple council members. That surprise vote in May prompted state lawmakers to threaten to force Charlotte and other local governments to repay hundreds of millions of dollars spent on the project. The council reversed course in September.
Some people likened Raki’s tactics to blackmail, he told the Observer after the council’s May vote.
“When they don’t meet our threshold, we should not endorse those individuals. Now, if that’s what somebody’s calling blackmail, then they need to look at the definition of the word, and they need to understand that advocacy demands accountability,” he said. “We are very much about endorsements, not entitlements.”
Raki resigned from his BPC leadership role in September shortly after Hill raised concerns relating to his company, WBTV reported.
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No state or federal agencies have said they are investigating the McGregors, but their work apparently precipitated the controversy after Hill’s memo and an employee submitted a human resources complaint.
The complaint filed Aug. 21 and later obtained by the Observer alleged then-board Chair Stephanie Sneed insisted the district make monthly payments to Qonnect without an official contract and despite warnings the payments violated board policy.
Those payments were part of a deal with law firm Poyner Spruill for services related to a teacher housing initiative, the complaint said.
Poyner Spruill later entered into an agreement with Qonnect to consult on the project. Qonnect would receive a monthly retainer of $30,000 paid by the district to Poyner Spruill. Those details were not in the contract approved by CMS.
Public records show CMS made monthly payments to Qonnect from April 10 through Aug. 4, totaling $150,000.
The board separately contracted Poyner Spruill for a compliance audit from June through September, for which the law firm again hired Qonnect for $132,000 of the up-to $220,000 audit, the Observer previously reported. Hill called the contract “nonsensical” in her memo and said McGregor was not qualified to perform the contracted services.
Hill questioned the board’s oversight of the payments and accused it of extortion.
The CMS board voted 5-4 to fire Hill one week later. Sneed resigned as chair during the same meeting, though she remains on the board.
Outside of CMS, questions emerged about the McGregors’ work with the county and sheriff’s office. WSOC reported Sneed and McGregor made a joint pitch to the Mecklenburg County Sheriff’s Office for a $400,000 consulting contract. And former Mecklenburg County Manager Dena Diorio told WFAE last week the county had concerns about SYDKIMYL dating back to 2025 and that Raki threatened to sue her during a meeting about the county cutting funding if she publicly alleged he had a conflict of interest.
Mecklenburg County Manager Mike Bryant told commissioners in a Sept. 25 email obtained by the Observer the county has not found any past agreements with Qonnect. But the county paid for $3.1 million in services from SYDKIMYL between fiscal years 2020 and 2025. The county terminated the agreement last year.
The Poyner Spruill contract isn’t the first time CMS hired the McGregors.
Raki was a senior vice president for Novant Health in 2022 when he was tapped to join the superintendent’s cabinet as chief executive in residence. He helped with corporate engagement and systemwide changes under a partnership with the Charlotte Executive Leadership Council, the Observer reported.
In a news release announcing McGregor was going “on loan full time to the school system,” Novant said he had “a track record of delivering transformational change, effective relationship management, outstanding customer experiences and expert navigation of challenging, changing and volatile markets.”
Many political leaders knew him generally as a Novant executive but never had a direct relationship with him until he pivoted to the school district, according to multiple political insiders. The role marked an inflection point.
He began showing up to public events and interacting with city leaders and got heavily involved with the BPC.
Raki’s district position included a $130,000 consulting contract with CMS set to end in July 2025. Hill said she chose not to renew Raki’s contract for another term.
“I became concerned that Mr. McGregor was looking to take advantage of his role as Executive in Residence, his proximity to sitting members of the Board of Education, and his association with candidates running for seats on the Board of Education,” Hill wrote in her Sept. 16 memo.
In October 2024, while Raki was still a chief executive with the school district, CMS entered into a $325,000 consulting contract with his wife’s firm. The district had worked with SYDKIMYL in some capacity since 2019, but the expansive new contract would have Kimberly provide coaching for principals at 10 CMS middle schools as well as three assistant superintendents.
The board later increased the contract amount to $500,000 at the recommendation of CMS executive staff, who pointed to improvements in test scores as evidence of the program’s success.
Three board members voted against the contract, arguing the district could instead hire more counselors and questioning whether it presented a conflict of interest given Raki’s connections to CMS and SYDKIMYL. Kimberly told the Observer at the time that her CMS work “doesn’t have anything to do with my husband.”
The district renewed SYDKIMYL’s contract to run through January 2026 at a price of $180,000 — below the $250,000 threshold requiring board approval.
All three board members who opposed the contract — Lisa Cline, Melissa Easley and Summer Nunn — left the board at the end of the year. Nunn chose not to run while Cline and Easley lost their reelection bids.
In her memo, Hill said Raki was “very upset” with the three board members who voted against his wife’s contract. He wanted to elect candidates who would approve additional SYDKIMYL contracts, she said.
Raki made waves by publicly endorsing CMS candidates before his tenure was up, including two who were running for Nunn’s and Easley’s seats. He said the endorsements had to do with who he felt was supporting, or not supporting, Hill.
His choice for Nunn’s seat was Anna London, the CEO of Charlotte Works. Raki served on the Charlotte Works board. His choice for Easley’s seat was Charlitta Hatch, one of Kimberly’s former students.
Public records from Mecklenburg District Court show the McGregors faced multiple lawsuits over unpaid debts and a nearly six-figure tax lien from the IRS.
Raki’s first court record dates back to 1991 when an apartment complex in Greensboro filed multiple small claims suits for money owed, and later for possession of property. The McGregors also faced two small claims suits from healthcare providers in 1997 and 2003.
In 2014, the State Employees’ Credit Union sued Raki for a $99,000 debt that he would pay in full, plus $15,000 in attorney fees, after a trial by judge.
A property owners association placed three liens on McGregor’s property in November 2011, May 2015 and May 2018 totaling more than $2,000.
Then, in 2020, the IRS placed a federal tax lien worth more than $96,000 against both McGregors. They paid off the debt in full 19 months later.
And in May Synchrony Bank filed suit against Raki for an outstanding account balance of more than $3,600.
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Rebecca Noel and Mary Ramsey contributed to this report.
