fb-pixel Skip to main content

Madison Park to launch national search for its eighth headmaster in eight years

Madison Park Technical Vocational High SchoolThe Boston Globe/Boston Globe/File 2012

Boston public schools will soon be launching a national search for a new headmaster at Madison Park Technical Vocational High School, one of the city’s most beleaguered schools.

The new hire will be the eighth school leader — permanent or interim — overseeing Madison Park in eight years, according to information from the district.

The longest serving was former headmaster Charles McAfee, who left in 2012 after a dozen years. But after that, the next five, including some besieged by controversy, have served no longer than one year or a little more than two years.

In new developments revealed this week, the district has sidelined the school’s current leader, Brett Dickens, and put the headmaster at the John D. O’Bryant School of Mathematics and Science temporarily in charge of both schools, which share a complex in Roxbury.


Madison Park’s popular executive director, Kevin McCaskill, is also out, headed to a new role at district headquarters.

A district spokesman said Superintendent Brenda Cassellius announced roughly a half dozen leadership changes last week as part of her effort to shore up academics, particularly in the district’s lowest-performing high schools.

In a statement, officials said Cassellius’ strategic investments in the district’s lowest performing schools must continue, calling it “more urgent than ever.”

In addition to the Madison Park reshuffling, Andrew Bott, who resigned as superintendent of Brookline Public Schools in July, will take the helm at Brighton High School in the fall, following the departure of Rob Rametti, district officials said.

Will Thomas, principal at Charlestown High School, will be reassigned to New Mission High School and Boston Community Leadership Academy, which are housed in the same Hyde Park complex. And Joel Stembridge, a former Boston school administrator who most recently served as principal of Newton South High School, is returning to the district to lead Charlestown.


Supporters of Madison Park say they worry the perpetual change has contributed to the school’s woes. The school, deemed underperforming by the state, enrolls high numbers of English learners and students with disabilities, many of whom get assigned there regardless of their interest in a technical education. The four-year graduation rate is more than 68 percent, data show.

In a scathing audit earlier this year, the state’s Department of Elementary and Secondary Education criticized the turnover at the top of the district — four permanent or interim superintendents in six years — and chronic change at the principal level.

The audit blamed a revolving door of district leadership, noting that in recent years district officials have lacked a “districtwide strategy to strengthen rigor" and knowledge about what is being taught in all the schools.

The shakeup at Madison Park includes McCaskill, the executive director, who is moving to the central office to assist with high school redesign efforts, officials said.

But advocates decry the move, saying his loss will be a blow to students who are reeling from the coronavirus’ impact on school closings.

"For them to be traumatized by the absence of the strong figure at Madison Park at this particular time is also doubly traumatizing,'' said Barbara Fields, a former Boston educator and member of the Black Educators Alliance of Massachusetts.

The O’Bryant headmaster, Tanya Freeman-Wisdom, will oversee the Madison Park educational complex on Malcolm X Boulevard in Roxbury, effective July 1. A national search is being launched to find permanent leadership at Madison.


Dickens, a former Madison Park assistant headmaster, has been headmaster since December 2017 and will for the time being report to Freeman-Wisdom.

Madison Park’s leadership has been plagued by controversy over the years. In 2013, acting headmaster Queon Jackson was placed on administrative leave amid a federal probe of his alleged role in a multiple-state credit fraud ring. No criminal charges were filed. The leave dragged on for more than three years, and the school system finally brought him back for job in the central office.

In September 2014, Diane Ross Gary resigned as headmaster after the school department learned she had not gained certification to lead a school in Massachusetts. The revelation followed a scheduling snafu that left many students and teachers without class assignments when the school year began. Al Holland, a former headmaster of the Jeremiah E. Burke, led the school on an interim basis during the 2014-2015 academic year.

Officials hired Shawn Shackelford as headmaster and McCaskill as executive director in 2015 in a bid to restore public confidence. But in late 2016, Shackelford was placed on paid leave and McCaskill, who oversees vocational programs and partnerships with area businesses, assumed Shackelford’s responsibilities along with his own duties.

The school system never disclosed why Shackelford was placed on leave. He no longer works for the school system.

In an e-mail dated April 27, Dickens said she will be not returning to the school next fall.


"This was very disappointing to me as I have never been in a school that I cared so deeply about and that energized me so much,'' Dickens wrote, noting that Madison is full of talented students and staff.

McCaskill, in an e-mail obtained by the Globe, said he was “forever grateful” to serve the school for the past five years.

"There was never a moment that I wasn’t proud to tell anyone who would listen that worked at Madison Park,”he wrote.

Although most of the changes are happening at the high school level, the principals at Roger Clap and Mason elementary schools — Carolyn Allston and Lauretta Lewis-Medley, respectively — will swap positions.

In addition, Kimberley Williams, principal of the Kilmer K-8, will take over as leader of the Edison K-8 to replace principal Sam Varano, who had previously announced his departure.

Meghan E. Irons can be reached at meghan.irons@globe.com. Follow her on Twitter @meghanirons.