Just who is Raki McGregor, the man at the center of the CMS scandal?

Much of former Charlotte-Mecklenburg Schools Superintendent Crystal Hill’s memo that alleges financial irregularities in the district focuses on one man: former Novant executive Raki McGregor.

Hill alleges that board member Stephanie Sneed went behind her back to ensure McGregor received a $30,000-per-month subcontract — after the McGregor family lost more than $1 million in funding when the county and CMS terminated contracts with its consulting company, SYDKIMYL.

In Hill’s 14-page timeline of events, the McGregor name and SYDKIMYL appear 77 times.

The former superintendent’s memo has prompted reviews by the state auditor’s office and Department of Public Instruction and investigations by the State Bureau of Investigation, the Department of Public Instruction and, now, the FBI.

Just who is Raki McGregor? And how did he come to be at the center of the CMS storm?

When McGregor tells his life story, the anecdotes he uses have a common theme: Overcoming.

After he graduated from high school in Greensboro, McGregor attended North Carolina A&T but dropped out in 1991 because of bad grades.

He said he then worked in fast food and had a brush with the law.

In a 2016 video, he talked about growing up in a Muslim family — and how it was a “tremendous obstacle” to connect with his father after becoming a Christian.

“My father was a devout Muslim and a man of strong discipline and belief, and me bringing Christianity into the household was not necessarily welcome,” McGregor said. “He and I were able some years later to mend that because he saw that my faith drove me, and one of his beliefs was whatever a man believed in, so long as he lived his life that way, was acceptable.”

McGregor returned to school and got his degree. He began a successful corporate career, with stops at Coca Cola Consolidated and TIAA. Ten years ago, he began working in business and technology at Novant.

His public speeches often blend faith and inspirational talk that could come from a locker room.

“I define success first by your foundation,” McGregor said. “What is it that you believe in that’s greater than yourself? I believe any person — male or female — if they have a strong, faith-based foundation, then all things are possible.”

I have covered politics in Charlotte for 20 years. For much of that time, McGregor was not particularly well known.

That changed earlier this decade.

As he climbed the corporate ladder and became involved with CMS, McGregor became a Charlotte insider. He played roles in the influential Black Political Caucus of Charlotte-Mecklenburg, attended galas, hung out with local business leaders and political types. He held court during breakfast at the Community Matters Cafe near uptown.

His family’s profile grew, too. Daughter Sydney McGregor was on Netflix’s Temptation Island. His son, Myles McGregor, started a black car service and was profiled in local media as Hugh McColl’s chauffeur. In 2018, McGregor, along with Sydney and Miles, gave his wife, Kim, an LLC as a Christmas gift, Kim McGregor told VoyageRaleigh magazine in 2024. The family named it SYDKIMYL — Sydney, Kim, Myles.

McGregor, who often wears bow ties, leaned into fashion. He joked to the Sarah Stevenson breakfast club about his success. He and his wife built a modern home in the historically Black McCrorey Heights neighborhood earlier this decade. (He would later become a vigorous opponent of the Interstate 77 toll lanes because the project would encroach on his neighborhood.)

“They said, now that you have made all of this money, are you going to change? Damn right I’m going to change,” McGregor said to laughter. “But the change is an elevation. The change is: We are going to have a good time, we are going to work hard, we are going to play hard. And we are going to bring others along with us. I don’t distance myself from my Nation of Islam start because it’s a part of my becoming.”

McGregor hasn’t spoken to the media since the scandal broke. He didn’t respond to a request to be interviewed for this story.

Charlotte CEOs bring McGregor to CMS

In 2022, the Charlotte Executive Leadership Council inserted McGregor into Charlotte-Mecklenburg Schools as an executive in residence. Novant loaned him to the district.

The idea: use McGregor’s executive experience for a year or so to make CMS more efficient and effective.

Former CMS board member Jennifer De La Jara said she hoped McGregor would ask the Charlotte business community to lobby Republican lawmakers to raise teacher pay. 

But she said some cabinet members told her he was heavy-handed. She coached him to use a different approach.

"To his credit, he did start to add, 'I'm not an educator,' before giving his opinions, and that helped,” she said. “You have to remember that he was in a room full of educators with doctorates in education, so some of his advice was welcomed and some was misplaced because he didn't know this profession." 

In spring 2023, the board was voting to name a permanent superintendent. Interim superintendent Crystal Hill was allied with McGregor.

“The day before the superintendent vote, he called me to pressure me to vote for Dr. Hill,” De La Jara said.

She said she told him it wouldn’t be ethical to disclose whether or not Hill was a finalist.

“And since he clearly has such a strong interest in selecting the next superintendent, (I told him) he should probably go down to the Board of Elections and file to run for school board,” she said.

Hill was hired as superintendent, and for the next two years, CMS insiders say McGregor, Hill and new board chair Stephanie Sneed were a triumvirate.

SYDKIMYL had an annual tutoring contract with Mecklenburg County worth about $500,000. SYDKIMYL also had an annual consulting contract with CMS for $325,000, later raised to $500,000. A minority of school board members questioned whether the district was getting its money’s worth. The consultant later received another contract for $180,000 for six months of middle school principal coaching.

Hill gets uneasy

In fall 2025, McGregor began campaigning with school board candidates who were running to replace the three board members who had questioned the SYDKIMYL contract. McGregor’s candidates won, which seemingly increased his influence over the board.

But Hill said she was alarmed by McGregor’s campaigning, which was highly unusual for a CMS executive. Staff do not take sides in board elections. Here’s what Hill wrote in her memo, released last month:

“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. Mr. McGregor was very upset with the three Board members who voted against the SYDKIMYL contract. I believe he wanted to help get candidates elected to the Board who would approve additional SYDKIMYL contracts.”

That was Hill’s recollection of June 2025. Soon after, The Charlotte Ledger wrote about McGregor’s campaigning against the board members who had rejected the SYDKIMYL contract. 

“Although I had previously considered offering Mr. McGregor another contract as Executive in Residence, I was very uncomfortable with the potential and perceived conflicts of interest involving SYDKIMYL, and the continued public scrutiny,” Hill wrote in her memo. “I informed Mr. McGregor that he would not be offered another contract as Executive in Residence. I called Chair Sneed twice to discuss the separation from Mr. McGregor. She was not supportive of this decision.”

Hill wrote that in November 2025, she met with newly elected board member Shamaiye Haynes. The former superintendent wrote that Haynes told her that “her main purpose as a school board member was to make sure ‘black businesses like SYDKIMYL get contracts’ (or words to that effect). I was surprised by this response because she specifically mentioned SYDKIMYL.”

In addition to Hill cancelling the SYDKIMYL contract and McGregor’s executive in residence position, the McGregor family had already faced another financial setback a few months earlier. Former Mecklenburg County Manager Dena Diorio ended the county’s SYDKIMYL contract, in part because she didn’t think the organization was serving enough kids.

Raki McGregor had said SYDKIMYL was his wife’s business, so Diorio said she was surprised that he came to lobby her to keep the contract. She said he threatened to sue if she said publicly that his role as both a CMS executive and contractor might pose a conflict of interest.

“It’s shocking, if you ask me. It raises a lot of questions for me,” Diorio said. “I mean, again, I had been doing this for a long time, and you learn to trust your instincts, and my instincts were saying there was just something icky about it.”

Hill’s memo then outlined how, in her opinion, board member Sneed quietly secured McGregor a $30,000-a-month consulting contract to work on an affordable housing project for teachers. The superintendent alleges in her memo that Sneed and board members began pushing people out who could act as a check against McGregor getting more money.

The board fired Hill in September.

That prompted the audits and investigations by state and federal agencies.

Commissioner questions CELC role

Mecklenburg commissioner and former CMS board member Arthur Griffin said the CELC should answer questions about McGregor’s activities at the school district, since they recommended he work there.

“They’re the ones who created the executives in residence with CMS and there’s been no discussion with the media that I can tell about the folks who thought this was a good idea,” he said.

The CELC includes business leaders like Gene Woods of Atrium Health; Ric Elias of Red Ventures; Sharon Garber of UNC Charlotte; and David Longo of CBI Workplace Solutions.

WFAE asked the CELC whether the organization was OK with McGregor lobbying for his family to receive contracts while he was an executive in residence with CMS. The organization declined to answer that question and said it “remains steadfast in our commitment to the success of Charlotte’s education system. We will continue to evaluate the ongoing situation and will work with CMS staff to determine our path forward.” 

This spring, Hill said McGregor and Sneed continued to lobby her to bring SYDKIMYL back.

Publicly, McGregor wasn’t weighing in. He said he would distance himself, saying it was his wife’s business.

He did appear in April on a podcast run by his wife Kim and daughter Sydney. It’s called The Prettiest Podcast.

He dabbled in philosophy and the idea of personal transformation.

“Does the caterpillar know that he’s a butterfly? No, not at all,” he said. “But does the butterfly know that he used to be a caterpillar? Yes.”

His wife and daughter were impressed.

“That’s deep. That’s really deep,” they said.