Homing in on new Boston superintendent

Is local finalist in the driver’s seat?

THREE FINALISTS HAVE BEEN NAMED in the search for a new Boston school superintendent, but it’s hard not to wonder whether home field advantage will be what matters in the end.

Look no further than the front page of today’s Boston Herald, where Boston Latin graduate and local school leader Oscar Santos gazes earnestly at readers next to a headline reading, “Our Saving Grace.” Flip inside and there’s a piece making the case for Santos — authored by Santos — under the headline in the print edition, “Boston’s own makes super case.”

Maybe the two other finalists, both from out of state, will get similar moments of Herald glory, but they shouldn’t hold their breath.

Meanwhile, the Globe offers a quick first take on what the three finalists say they would bring to the job of helming the state’s largest school district. While Santos offers comments in an interview with reporter James Vaznis, the other two finalists, Marie Izquierdo, chief academic officer for Miami-Dade County Public Schools, and Brenda Cassellius, former state education commissioner in Minnesota, provided statements to the paper.

Advantage Santos.

But it’s not just the media optics that may give Santos an edge. The search comes after the aborted tenure of Tommy Chang, who arrived in Boston in 2015 but was run out of town in 2018 with two years left on his contract after stepping on political and policy minefields and not clicking with Mayor Marty Walsh.

That has framed the search for a successor, in part, as a quest for someone who will be able to better navigate the complex issues facing the schools and understand the political sensibilities that are always part of big decisions facing the district. In that context, who could better fit the bill than someone already steeped in the local ways?

After being raised in the city by an immigrant mother, Santos eventually went on to teach in Boston, serve as a principal in the district, spend three years as superintendent in Randolph, and then land at Cathedral High School, where he has run the Boston Catholic preparatory school since 2013.

“I grew up in Boston,” Santos tells the Globe. “I not only know the geography of the city, but I know the feeling of the city. I understand the scars of Boston busing. I understand the challenges and the inequities that have existed. I know it because I have lived it. It’s not something I have read in a book.”

City Councillor Annissa Essaibi George told the Herald she’s interested in a candidate with “deeper roots to Boston,” but said she’s looking forward to hearing what each candidate could contribute.

Meet the Author

Michael Jonas

Executive Editor, CommonWealth

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

The Globe sought out education leaders who could comment on the track record of each finalist. While people with serious education credentials offered praise for Izquierdo and Cassellius, it was a very familiar voice offering testimonial to Santos: one-time Boston superintendent and former Boston Latin School head master Michael Contompasis.

No one is saying the fix is in, but it’s hard not to sense an echo of the recent state education commissioner search, which featured two out-of-state women candidates and Jeff Riley, a former Boston principal and administrator who was serving as state-appointed receiver for the troubled Lawrence schools. There was a case to be made for all three, but the state education board wound up going with the one whose track record they knew best and who would have a head start in dealing with all the particulars of place.