The Revenge of the Old Guard: What Happens When a New Superintendent Tries to Change the Culture

MoCo's Voice | Public Accountability Series

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There is a pattern. It is documented. It has played out in school districts from California to North Carolina, from Utah to Massachusetts. And it is playing out right now in Montgomery County.

A school district struggles for years. Test scores stagnate. Teachers leave. Low-performing schools accumulate. The community demands change. The board hires a new superintendent, often someone from outside, often someone with a different background from the previous leadership, often someone hired precisely because they are not part of the system that failed. And then, almost immediately, the resistance begins.

Not resistance from students or parents who want better schools. Resistance from the people who benefited from the old system, the ones who had power, access, and protection under the previous administration. The ones who, when a new leader arrives with accountability and high expectations, suddenly discover that they have grievances.

This is not a Montgomery County story. This is an American story. And understanding it is essential to understanding what is happening to Dr. Karen Roseboro right now.

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The Pattern Has a Name

Education researchers have documented this phenomenon extensively. Dr. Shawn Joseph, Assistant Professor of Educational Leadership and Policy Studies and Co-Director of the Urban Superintendent Academy at Howard University, published a case study in the Journal of Cases in Educational Leadership titled "Swimming Against the Current: Resistance to a Black Superintendent's Fight to Lead With Equity in an Urban School District." [1]

The study examined a Black superintendent hired to lead a large urban district in the South, hired specifically to improve outcomes for students of color and to shift a culture of low expectations. Within three years, the superintendent was gone. Dr. Joseph documented three incidents during the superintendent's tenure that the superintendent believed were racially motivated. The school board and community downplayed race as a factor. The community's racial bias, Dr. Joseph concluded, led to the superintendent's departure before the work could be completed.

Dr. Joseph's conclusion was direct: "The true stories of Black superintendents must be told. Prejudice and racism played a factor in this school leader's ability to improve outcomes for children." [1]

This is not an isolated academic finding. It is a pattern that has repeated itself in district after district, and it follows a recognizable sequence.

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The Playbook

The tactics used to undermine new superintendents, particularly Black women hired to reform struggling systems, follow a recognizable playbook. Understanding the playbook is the first step to recognizing it when it is being used.

This table is not a theoretical construct. Each item in it is documented in the research literature on superintendent resistance, and each item has a direct parallel in what is happening in Montgomery County right now.

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Case Study: Salt Lake City, Utah

In 2021, Salt Lake City School District hired Dr. Timothy Gadson III as its first-ever Black superintendent, and the first Black educator ever to lead a Utah school district. He was hired after a national search, with strong community support, to lead a district that needed significant improvement. Within approximately one year, he was placed on administrative leave. Within fourteen months of starting, he had resigned.

The NAACP Salt Lake Branch President Jeanetta Williams called the board's actions "blatant racial discrimination." [2] Black community leaders held press conferences saying that the same behaviors that led to his placement on leave would not have been considered problematic for a white superintendent. The Salt Lake Tribune reported that the district had four superintendents in three years, with board infighting, accusations of racial discrimination, and a blistering audit marking what one reporter called "three tumultuous years." [3]

Dr. Gadson was the first Black educator ever to lead a Utah school district. He lasted less than two years.

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Case Study: Sequoia Union High School District, California

In April 2021, the Sequoia Union High School District in California selected Dr. Darnise Williams as its first-ever Black female superintendent, with her tenure beginning July 1, 2021. She came with a record of accomplishments and a commitment to equity. In December 2022, less than two years into her tenure, she resigned following two closed-session board meetings that the community was not told about.

Community members packed the board meeting where her departure was announced. Teachers, parents, and staff accused the board of anti-Blackness and a lack of transparency. "We're not dumb, we all know she was pushed out," said Pablo Aguilera, a Sequoia history teacher. [4] The board refused to explain the reasons for her departure. They paid her $299,000 in a separation agreement and immediately moved to name an interim superintendent.

The pattern was identical to what researchers describe: closed sessions, no public explanation, a "mutual agreement" that the community immediately recognized as a forced exit, and a board that celebrated with cake while the community grieved.

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Case Study: Robeson County, North Carolina

In 2020, the Robeson County Board of Education voted 6-5 to fire Superintendent Dr. Shanita Wooten, with the board chairman casting the deciding vote. The stated reason was that the board wanted to "go in a different direction." [5]

Dr. Wooten had been hired in 2018 to lead a district that needed improvement. She was fired before she could complete her work. The 6-5 vote, a single-vote margin, with the chairman breaking a 5-5 tie, reflected a board divided along the same lines that divide boards across the country when a new superintendent tries to change a culture that some members of the board were invested in protecting.

Robeson County is in North Carolina. It is not far from Montgomery County. The pattern is not unique to urban districts or to distant states. It happens here.

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What the Research Says About Who Gets Targeted

The data on who faces the most resistance is unambiguous. According to the 2025 AASA Superintendent Salary and Benefits Survey, Black superintendents represent less than 5 percent of all superintendents nationally, despite Black students representing a significantly larger share of the student population. [6]

The same survey found that Black superintendents have shorter tenures in their current positions than their white peers, more than three-quarters of Black superintendents have been in their current role less than six years, compared to 63 percent of white superintendents. [6] This is not because Black superintendents are less qualified. The same survey found that 80.4 percent of Black superintendents hold a doctorate, compared to 41 percent of white superintendents. [6]

Black superintendents are more credentialed. They stay less long. The research does not leave the reason ambiguous.

Harvard's Jennifer Cheatham, who has studied and supported superintendents for decades, described the current environment plainly: communities that are undergoing significant demographic change, where the student population has shifted while the power structure has not, are the places where this kind of organized resistance is most likely to occur. [7] "What we need in school systems across the country is stability in leadership right now," she said. "It's not only that the kind of local politics has become a huge distraction, but superintendents are leaving their jobs." [7]

Montgomery County's student population is majority students of color. Its previous leadership structure was not. Dr. Roseboro is the first Black female superintendent in the district's history. The research tells us exactly what kind of community this is, and exactly what kind of resistance to expect.

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The Specific Tactics in Montgomery County

What is happening in Montgomery County is not a spontaneous community uprising. It is a coordinated campaign that follows the documented playbook with precision.

A school board member, Bryan Dozier, refused to sign the new superintendent's employment contract. That is not a policy disagreement. That is a signal, sent to the superintendent and to the community, that her authority is not fully recognized by a portion of the board.

A county commissioner, David "Chip" Hurley, used a budget meeting to question the superintendent directly about a JV baseball program. County commissioners do not oversee school operations. That was not a budget question. That was a performance, a public display of disrespect designed to signal that the superintendent is not protected by the normal boundaries of her office.

A local newspaper, the Montgomery Herald, has published a pattern of coverage that amplifies complaints and criticism while providing minimal coverage of the district's documented progress. The NC Department of Public Instruction came to a board meeting and said the district is moving in the right direction. That is not a minor data point. That is the state's own assessment of the superintendent's work. It received far less coverage than the complaints.

A former principal, who resigned from the district, has engaged publicly as a critic, lending an air of insider credibility to the opposition while having no current accountability for the outcomes of the children in Montgomery County schools.

Each of these tactics is documented in the research literature. Each of them is designed to do the same thing: make the superintendent's position untenable before her work can be evaluated on its merits.

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What Communities That Protect Their Superintendents Get

The research on this is as clear as the research on turnaround timelines. Districts that protect their superintendents' ability to do the work see improvement. Districts that yield to organized pressure and remove leaders before the work is done return to the same cycle of instability, low performance, and declining opportunity for children.

Mark Bedell became superintendent of Kansas City Public Schools in 2016. The district had been unaccredited for 16 years, and the 27 superintendents who preceded him had averaged just 1.8 years in the role. People told him the situation was so bad that he would be "run out" in two years or would leave on his own. He stayed. He became the district's longest-tenured superintendent in over 50 years. His team restored accreditation to the district for the first time in 20 years. [8]

That is what happens when a community decides to protect its superintendent instead of yield to its old guard.

Montgomery County had six low-performing schools. The state said the district is moving in the right direction. The research says it takes three to five years to know if that direction will hold. Dr. Roseboro has been here for nine months.

The old guard is counting on this community not knowing the playbook. Now you know it.

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References

[1] Joseph, S. (2023). "Swimming Against the Current: Resistance to a Black Superintendent's Fight to Lead With Equity in an Urban School District." Journal of Cases in Educational Leadership, 26(2), 87–100. https://journals.sagepub.com/doi/10.1177/15554589231164366

[2] Williams, J. (2022). NAACP Salt Lake Branch statement on Dr. Timothy Gadson. Reported in: "School board meeting reveals split opinions on Salt Lake district's handling of Gadson situation." KSL.com, August 2, 2022. https://www.ksl.com/article/50451152/school-board-meeting-reveals-split-opinions-on-salt-lake-districts-handling-of-gadson-situation

[3] "A revolving superintendent's door, board member squabbling and a blistering audit mark three tumultuous years for the Salt Lake City School District." City Weekly, January 31, 2023. https://www.cityweekly.net/news/a-revolving-superintendents-door-board-member-squabbling-and-a-blistering-audit-mark-three-tumultuous-years-for-the-salt-lake-city-school-district-19520526

[4] Butt, R. (2022). "Community backlash as Sequoia district's first Black female superintendent and board of trustees part ways." The Raven Report, December 15, 2022. https://www.ravenreport.org/5107/showcase/community-backlash-as-sequoia-districts-first-black-female-superintendent-and-board-of-trustees-part-ways/

[5] "Robeson County school board takes 'different direction' in firing superintendent." The Fayetteville Observer, September 15, 2020. https://www.fayobserver.com/story/news/2020/09/15/robeson-county-school-board-takes-different-direction-firing-superintendent/5803051002/

[6] AASA, The School Superintendents Association. (2025). 2024–2025 AASA Superintendent Salary and Benefits Survey. Reported in: "Less Than Five Percent of School Superintendents in the United States Are Black." Journal of Blacks in Higher Education, July 21, 2025. https://jbhe.com/2025/07/less-than-five-percent-of-school-superintendents-in-the-united-states-are-black/

[7] Cheatham, J. & Cohn, C. (2022). "The Superintendency and Culture Wars." Harvard Graduate School of Education EdCast, October 21, 2022. https://www.gse.harvard.edu/ideas/edcast/22/10/superintendency-and-culture-wars

[8] Riddell, R. (2025). "How challenges, experiences shape superintendents of color." K-12 Dive, March 14, 2025. https://www.k12dive.com/news/how-challenges-experiences-shape-superintendents-of-color/742618/