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Boston mayoral candidate Annissa Essaibi George inspired as a teacher and businesswoman

City Councilor and mayoral candidate Annissa Essaibi George.Craig F. Walker/Globe Staff

In her 13 years at East Boston High School, Annissa Essaibi George served as a mother figure to a host of teenagers, an advocate for her students, including those in crisis, and a dreammaker who made Joi Joy’s prom night a magical experience.

“She crowned me prom queen. . . . It was a sentimental moment,” said Joy, a former Eastie High student, recalling the Luther Vandross-themed event 16 years ago.

Joi Joy, is a former student of Annissa Essaibi George and a current East Boston High School teacher.Jonathan Wiggs/Globe Staff

During her campaign for mayor, the Dorchester councilor and proprietor of the Stitch House yarn and fabric shop has made her experience as a teacher and small-business owner a cornerstone of her mayoral campaign and a key distinction between her and her rival, City Councilor Michelle Wu, who is leading in a new poll in the historic race.


It’s a point she has made repeatedly on the campaign trail and in her campaign ads. She returned to that theme during the race’s two televised debates so far, contending that being a teacher gave her a front-row seat to needs of families in the city.

“As a teacher I know how to do this work,” she said during WBZ-TV’s Oct. 13 debate. “We want to fix the Boston Public Schools. . . . I’ll get it done.” Seconds later, she highlighted her record as a small-business owner as another crucial experience that has prepared her to be mayor.

Her former students effusively praise Essaibi George for her patience and guidance in and out of the classroom, bolstering the candidate’s narrative to voters that her teaching — and business — experience puts her in the best position to be chief executive of this city.

Essaibi George worked full time at East Boston High from 2001 to 2006, according to Boston public school records. After her triplets were born, she switched to part time for roughly another decade, beginning around 2007. She taught electives to juniors and seniors, including economics, entrepreneurship, and introduction to psychology. She said her parents inspired her to teach.


“Both my immigrant parents really valued education: the importance of receiving a good education, but also the role good schools and educators play in the community,” Essaibi George said. “It was about providing that great educational experience for other kids in the city I grew up in and paying it forward.”

Jane O’Leary, an assistant headmaster when Essaibi George was hired at Eastie High, said Essaibi George started as the school-to-career coordinator, which was partially funded by the Gates Foundation. At the time, the school had two career pathways — health professions, and travel and tourism — and Essaibi George taught those electives, O’Leary said.

When the Gates Foundation money ran out, Essaibi George began teaching other school-to-career pathway classes, including entrepreneurship, said O’Leary, who was involved in the school for nearly 40 years as an administrator and a consultant after retiring.

“She did a great job, but then she really wanted to teach,” O’Leary recalled. “She belonged in the classroom. She was wonderful, so she got hired.”

But her time as a teacher and operation of her small business also fit into a broader pattern of administrative lapses that runs throughout Essaibi George’s professional career. State records show she did not have a valid teaching license for most of the time she taught at East Boston High School. She also did not register her popular and successful small business, Stitch House, for the past four years, as required by the city.


To her students, Essaibi George was more than their teacher and the softball coach for the Eastie Jets. She was a confidante and supporter. As the senior class adviser, she raised money for the senior prom and scholarships. She also spearheaded “Flower Power” on Valentine’s Day, an event that allowed students to buy carnations for $1 to be delivered to their friends or secret admirers, O’Leary said.

Joy, the former student who took Essaibi George’s economics class during her senior year in 2004-05, recalled a teacher who grouped students in pairs to boost learning and creative thinking, who had command of the subject, and who found a way to bring out the best in her young charges.

“She was dealing with a lot of social emotional learning, because [that year]. . . we did have a few challenges,” said Joy, who appeared in one of Essaibi George’s campaign ads. “One of our own classmates was stabbed in front of our school. It was a very traumatic moment.”

As an assistant softball coach, Essaibi George never sat on the sidelines, never quit on her students, and always gave them lessons to last a lifetime — even as she juggled multiple things on her own, said Joy, who now teaches at Eastie High after being inspired by Essaibi George.

“She was always so busy, and she wore many hats,” Joy said, recalling Essaibi George’s juggling triplets and her duties at the time. “If you would have seen her Subaru back in the day with her triplets, you would have thought she was this person that had no structure. . . . Her car was always jam-packed with stuff and I’m like how [did you fit] triplets in the Subaru.”


Christian Serpas, who took Essaibi George’s general studies and introduction to psychology classes in the 2012-13 school year, said she kept an open mind and allowed students to collaborate and develop their own thinking.

“That was one thing that really intrigued me,” said Serpas, who described himself as a quiet, shy nerd in high school. As a senior, he ran for class president and lost. But he recalled Essaibi George stressing that he should speak up more and avoid mudslinging.

“ ‘You have to be genuine,’ “ he recalled her telling him. “I became the loudest person in the world.”

But Essaibi George was licensed for only five of the more than 13 years she taught at Eastie High, records from the state’s Department of Secondary and Elementary Education show.

She did obtain a waiver to teach political science/political philosophy without a license for grades eight through 12 that was good for roughly a month, from Dec. 9, 2002, to Jan. 3, 2003.

She got a Provisional license to teach that subject on Jan. 3, 2003, but she did not receive any other licenses with the state, records show.


A Provisional license is valid for five years of employment, said the state. That would mean Essaibi George was licensed only from 2003 to 2008. When a teacher’s Provisional license expires, the next step is to seek an upgrade to an Initial license and later a Professional license. Maintaining a valid license is “the individual educator’s responsibility, and the school district is responsible for ensuring that the staff they employ are properly licensed,” according to the state.

State licenses are necessary to confirm that teachers and administrators have the qualifications and basic skills required for their jobs. Candidates must pass the appropriate Massachusetts Tests for Educator Licensure for the content areas and grade levels they wish to teach.

Essaibi George was not alone as a teacher without a valid license in the city’s school system, reflecting a long, complicated problem that Superintendent Brenda Cassellius said she is trying to remedy.

Cassellius, whose license expired for a short period of time, said that Boston public schools is adding a position in the Office of Human Capital “to focus solely on licensure to monitor and ensure all new and current staff members obtain and maintain the appropriate licenses according to expectations set by the Department of Elementary and Secondary Education.”

East Boston’s current headmaster, Phillip R. Brangiforte, praised Essaibi George for her work and advocacy for students. She first announced her run for mayor outside the school.

But Brangiforte said that he was not privy to Essaibi George’s licensing situation when Brangiforte — then an administrator at Eastie High for 12 years — took over the school’s leadership a year before Essaibi George’s first run for city councilor in 2013. Brangiforte said she was instrumental to the school and noted that there are plenty of really good unlicensed teachers in the charter schools.

“She was a good solid teacher, an excellent teacher, and the kids loved her,” he said.

Essaibi George, through her campaign, said the lapse was an oversight. She explained that she “applied, took, and passed the test for her Initial license” years ago. But she said she did not know that she needed to take the extra step of going online and submitting a fee of about $25 to the state. “As a result, her license didn’t switch over to Initial,” her campaign spokeswoman said.

The councilor earned a master’s degree in education from UMass-Boston in 2008 and chairs the City Council’s Education Committee.

The campaign said “it’s unfortunate” that the situation came down to Essaibi George not realizing that she had to pay a fee to the state, adding that she was not aware that anything was amiss until it first was brought to her attention by reporters, years after she was elected to the City Council.

“This has nothing to do with her effectiveness in the classroom or professional development,” the spokeswoman said. “It was an oversight, and neither the state [nor] BPS flagged that anything was amiss.”

Essaibi George also did not register her Stitch House yarn shop as a business with the city from 2017 to last week, as required by the city, documents show.

She only renewed the business certificate after a Globe reporter inquired about it with the city clerk’s office.

After the reporter’s inquiry, an aide in the clerk’s office who had pulled the document for the Globe contacted Essaibi George and told her that the registration, first issued in 2013, had expired back in 2017. The councilor then went to the clerk’s office and promptly paid $65 for the renewal, the aide said.

The registration is good for four years.

Essaibi George again cited “an oversight” for why the registration lapsed, adding that she did not receive a notification from the city when it expired four years ago.

“When she was notified by the city recently, she re-registered immediately,” her spokeswoman said.

Essaibi George and her husband also have been late paying property taxes on their Dorchester home every year since at least 2014, the Globe previously reported. The couple is currently up to date, but records show late tax payments are part of a longstanding, broader pattern that includes their cars and businesses.

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