Obas pulled up pictures of Malcolm X, Rosa Parks and Thurgood Marshall on his laptop; he asked students if they felt any connection to those historical figures. He asked if they knew that Michael Jordan had been cut from his high school basketball team. And he asked them what they eventually wanted to be.
“It was the kids who, for some odd reason, didn’t think they could be great or successful. I wanted kids to actually see what they could possibly do,” Obas recalled. “No kid wakes up, comes to school, and says, ‘I want to be bad today.’ Kids never say that. I think there’s something in their way that causes them to not make the best choices. It’s up to us adults to really tap into them and bring out the best.”
Nearly a decade later, with a set of newly minted graduate degrees, Obas is now leading that Bridgeport school, still emphasizing the importance of relationships as principal.
Next year, he is take over at New Haven’s AF Amistad High, the charter network’s flagship school, where teachers are eager to implement his message after a recent crisis in leadership.
Obas will replace Morgan Barth, Amistad’s former principal, who announced his resignation in January hours after the Independent published two videos about the school: a security-camera clip of Barth shoving an student and a Facebook Live of former staffer, Steven Cotton, complaining about entrenched racism.
After that controversy, Obas said, he wants to get the school back to its founding values. He has drawn wide support in that mission.
Obas has been the subject of complaint about physical contact with students in the past; network leaders decided after looking into the complaint that it didn’t rise to the level of a major problem.
“Simon has a very strong track record of both supporting students’ academic achievement and creating a positive school environment where students, staff, and families come together. Simon has exceptional leadership skills and a deep commitment to doing right by our students,” said Dacia Toll, Achievement First’s co-CEO. “We are excited for him to lead the next chapter of AF Amistad High.”
Plans For Next Year
As he has done throughout his life, Obas said in an interview, he plans to focus on building relationships at Amistad. That means connecting with students who don’t understand the disciplinary system, with parents who don’t know what’s going on inside the building, with teachers who want to play a more active role in the school’s direction.
“This is where I started my career. It’s obvious that the school is going through a transition, through some tough times. I have a set of kids from my school that come here now, and I know the type of high school experience that I want them to have,” Obas said. “There’s a lot of relationship-building that needs to happen. Kids need to feel loved; they need to feel noticed and heard. That is something that, when I get here, is going to be a priority.”
Obas said he sees a need for “strict structure and rules.” He said that kept him in line during his childhood.
But he said the disciplinary system needs to be “consistent and fair.” He said that the school needs to do a better job of explaining why the school’s policies would matter in the real world.
He added that he wants to do a better job of connecting Amistad to the surrounding Newhallville and Dixwell neighborhoods. Over the summer, he’s planning to have staff do a “community walk,” to walk the streets where the students live, “to eat where they get food from” and “interact with people walking down the street.”
There At The Beginning
Growing up in Danbury as the child of Haitian immigrants, Obas said, he learned the value of relationships early on.
At the local public schools, he wasn’t a “straight‑A student,” especially in math. He had teachers who invested in him, “who got to know me as Simon and cared what Simon enjoyed doing.”
At home, he was the second-youngest among 10 kids. That gave him a chance to listen as his older siblings shared what mistakes they’d made in their schooling.
When he arrived at the historically black Johnson C. Smith University in North Carolina, he struggled to afford his classes. He made it, and became the first in his family to obtain a college degree.
He planned to go on to law school. Then. during his senior year, a Teach for America recruiter flew him to New York to see Harlem Children’s Zone, the renowned anti-poverty program that promised “cradle-through-college” services.
The experience was life-changing; Obas decided to go into education. “There was so much joy on their faces around learning,” he recalled. “I saw myself in a lot of those kids.”
Even though he didn’t get a spot with Teach for America, a recruiter told Obas to check out the rapidly expanding Achievement First network. In 2009, he applied to be Amistad High School’s student life coordinator and was accepted. He organized assemblies, prom, and the school’s first graduation ceremony, while working to buildup the school’s culture.
“It was the perfect introduction to education. It’s an organization that wants to serve children from the inner-city and give them a high-quality education. From a values standpoint, it made sense: equal opportunity is what I value and stand for,” Obas said. “I decided to stick with it.”
The “Reflection Room”
While he pursued a masters in social work at Fordham University in New York, Obas eventually took a job teaching eighth-grade reading in Bridgeport. That’s also where he started supervising the “reflection room.”
Bertram Johnson, Jr. — a former Achievement First student who previously told the Independent that Morgan Barth had shoved his little brother on the Bridgeport school’s front steps in 2013 — said that he remembered Obas, around the same time, making real connections with students.
Johnson called Obas “the perfect candidate” to take Barth’s place at Amistad.
Obas “played basketball with the kids at recess, helped troubled students remain calm and built a relationship with the students and faculty alike. He was loved by everyone,” Johnson recalled. “His rare ability to empathize with the students will be a great help in bridging the gap between students and teachers and restore some trust in the system. I genuinely feel as though he’s the perfect candidate to make the kids happy again.”
In 2012, Obas left to make the rounds at a series of charter schools.
He served as dean of students at KIPP’s NYC College Prep High School in the Bronx, the founding assistant principal of school culture at the independent Charter High School for Law and Social Justice also in the Bronx, and an instructional fellow at Uncommon Schools’s Brownsville Collegiate Charter in Brooklyn.
Obas also continued his studies at Fordham, beginning a doctorate in urban school leadership.
He’s currently wrapping up his dissertation, which asks what would happen if principals spent more face-time with students. As part of his research, Obas designed an experiment that measures student motivation after one-on-one meetings with the principal twice a week.
Eventually, AF Bridgeport Academy drew him back as principal.
Right away, internal staff survey results “soared,” rising at a faster clip than any other school in the network, Toll said. Test scores also went up by double digits, with every grade and subject seeing “significant” growth, she added.
Obas said that AF Bridgeport will always be like a home for him. He said he wouldn’t have left for any other school, except for New Haven’s Amistad, where he started his career.
“That’s where I really fell in love with education. That’s the school I genuinely love. If it were any other school [besides Amistad offering me a job], I would have said no, because Bridgeport is that special place to me,” he said. “The catalyst for our success is our relationships with students and families. If we have those authentic relationships and connections, we will be successful. From student investment to adult culture, I’d like to be remembered for making relationships a priority.”
Some former students said they worry that Obas has a track record of physical contact with students like Barth’s. One remembered watching him throwing a kid’s backpack in the trash.
Toll said that the network looked into these allegations and concluded that they were handled correctly.
Through a spokesperson, Toll declined to specify which allegations had been investigated. That’s despite facing accusations that she’d purposefully allowed Barth’s misbehavior to be kept from other Amistad staff; an outside law firm is now investigating whether she and other network leaders perpetrated a coverup.
“Given the needs at Amistad High, we took the principal appointment very seriously,” Toll said. “We investigated all incidents that were brought to our attention. Both AF and the school’s board are comfortable that Simon handled those incidents in accordance with state law and AF policy. Some of the rumors I have heard are blatantly untrue and unfair.”
Obas said that he too “welcomed” the background check.
“I know how important this role is, and I welcomed the investigation,” he said. “I was cleared, and I’m ready to move Amistad High forward.”
The Search For A Replacement
As it searched for a new school leader, Achievement First posted the open position publicly. The network even asked staff to offer other nominations, Toll said. Once applications were in, the network leaders conducted a “thorough interview process that evaluates candidates against our leadership competencies,” Toll said.
The network eventually told teachers that it had narrowed the search to three finalists. But two of them never showed up at the school. This week, Toll said that’s because Obas was the only finalist who actually met the network’s internal “leadership competencies.”
To vet him, teacher representatives visited AF Bridgeport Academy to interview faculty and students and to observe Obas at work, said Amanda Pinto, an Achievement First spokesperson. Obas also came to New Haven to meet with the high school’s staff, students and families.
The Achievement First network leaders presented Obas to the nine-member joint committee for an up-or-down vote in early March.
“Staff, student government members, and families provided positive feedback that heavily influenced the board’s decision to select Simon as principal,” Pinto said. They approved him unanimously.
The one-candidate process led some skeptics, like Cotton, who originally blew the lid on Barth with his viral Facebook Live videos, to question whether the fix was in from the beginning.
He questioned whether Obas will be independent enough to make the changes that students and staff have demanded.
“You’re trying to build good relationships with parents, scholars and teachers. You already told them three candidates are in the running for principal, yet only one is around and visible?” Cotton said. “The thing that bothers me about this is that Dacia said that Simon’s her first pick, that she and Simon have been working together for years, that he helped get Achievement First going. They kept in-house who they want, because they’re all friends.”
Cotton said that kind of relationship was what allowed Barth to take the top job at Amistad and later keep it despite behavior they later called “unacceptable” once it was leaked to the public.
“They do what they do to keep each other protected,” Cotton said. “That’s what I feel like is still going on again.”
Others argued the hiring process produced a promising leader.
Lauren Cohen, Amistad’s summer programs coordinator who helped draft a letter asking for staff to be involved in the search, said she feels “excited to see him make positive changes at our school.”
Khadijah Muhammad, the president of the network’s parent leadership council, said parents are “looking forward to this transition” as well.
“The parents and I have been at the table and have had input in this decision,” she said.
Overall, Obas said he feels ready to get started. He said he doesn’t feel “scared” or “nervous” about the task in front of him, just “lucky.”
“There’s a lot going on; I’m not blind to that. But I’m just here to do the work,” Obas said. “In a few months, once we start changing things around, people will see what Amistad stands for.”
What does the school represent to him?
“I want to show it’s a place of empathy and a place of love. It’s a place of learning. It’s a place that’s fun and where kids want to be,” Obas answered. When he was first hired at Amistad, “we were so small, it had that community feeling. That’s the Amistad I left, and that is the Amistad that I would like to see return.”