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Keith Allen, Port Chester’s First Black Asst HS Principal Understands The Assignment By Tatiana Pinheiro

Keith Allen, Port Chester's First African-American Assistant High School Principal pictured second from the right [Black Westchester]

This past fall the first African American Assistant Principal took office at Port Chester High School, in Port Chester, NY. According to the census.gov website, Port Chester in 2019 had an African American population of 4.1 %. Since then that population has decreased by almost 1 %. Today, Port Chester High School’s African American population falls at about 6.3%. With all the recent talk of equity, diversity and inclusion, Keith Allen’s role as ‘first’ is largely significant.

“I’m laying the foundation for things that may come after me. We all bring different perspectives and I’m okay with representing our black and brown kids”, Allen shared with Black Westchester. 

Almost a full year into the current school year, Allen sat down with me in the beginning of the term to acknowledge his transition into the new school year and admitted that it had its challenges, given the circumstances of the pandemic.

“I realize that there are gaps in terms of socialization because of the pandemic. Everyone is transitioning back into the system of school”.

But Allen was sure to get to work quickly, roaming the hallways getting to know the students inside and out of their classrooms. He understands the importance of identifying the needs of the kids to effectively serve them as Assistant Principle. He also understands the importance of providing students with the opportunity for representation and teaching them the value of their history. 

Allen has had his fair share of ‘first’. He was the only black teacher in Brewster Central District for 13 years, until he became the Assistant Principal there. While he served his 13 years as a teacher, he had an aid, a black woman, who he encouraged to go to school to get her degree so she could teach her own classroom full-time. Eventually, she acquired her bachelor’s and master’s degrees and became the second black teacher in the district. Her daughter followed her footsteps and then became the third.

“The gift I’m giving, I’ve got to support our people, all people”. 

Allen allocates a lot of his energy into creating a safe space for the kids and knows that it is vital to establish trust and understanding, acknowledging the various life circumstances each of the kids have. He also emphasizes the importance of exposure to diverse backgrounds and environments.

“In order for kids to leave their comfort zone, you create trust first. Once they make that decision to go outside of their comfort zone, let them know that you support their interest…you’ve got to get them to think beyond what they know”.

Allen is currently working on diversifying existing programs and expanding some of the after-school clubs like, the African American Club, by working closely with Ingraham Taylor, a long-time resident of Rye and board member of the Education Committee, and Committee Chair of the NAACP ACT-SO Coalition (Academic, Cultural, Technological and Scientific Olympics) of Westchester.

“Mr. Allen is an individual who is committed to empower and support the students to strive for success, and that’s all you can ever hope for”, says Taylor. 

When we last spoke, Allen had plans to bring in professionals of color, to show students that they can in fact be who they want to be in life. This school year, Allen has not neglected to put action behind his word. Students like Isaiah Dempson, Senior and Student Body President, believe that Mr. Allen has already made a positive impact. During Black History Month Allen made daily announcements to give a synopsis on Historical Black figures, he also brought in guest speakers from different professions like finance to share their success stories with students.

Dempson says, “We’ve never experienced a Black History Month like we did this year. In my previous years, the month of February felt like it went by quickly, but not this year. He really made it fun, and we learned so much! Mr. Allen hasn’t just been helpful with Black History Month but also Women’s History Month. He’s really trying to be there for all the students, and I think he’s doing a good job at it”. 

Allen also believes in building community and feels that it is equally as important that the families of students feel integrated and a part of their child’s educational experience. “I want to connect the communities to the school, there is a lot of disconnect and I just want them to know that they are welcome here…their input is important”. 

Allen hopes to see more equitable programing that celebrates the culture of all students in the next five years and says he will continue to work diligently to make that possible.


Tatiana Pinheiro is a character education instructor for a global non-profit organization. She enjoys writing poetry, critical essays, film, and photography. As an aspiring multimedia journalist, she hopes to use her platform to tackle issues like segregation, public housing, and education in and outside of Westchester County. She is currently working on an Instagram project called @nooomoreapologies which uses fashion, imagery, messaging, and juxtaposition to challenge stereotypes. ” I want people to understand that when you come from the hood or disparaging communities, you can defy the odds and be so much more than your expected to be. There is power in owning who and where you are in life, especially if it doesn’t fit the standard”. 

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Black Westchester - News With The Black Point Of View is an online news magazine for people of color for Westchester and the Tri- State area of New York at every economic level. Our mission is to promote the concept of “community” through media.

2 Comments on Keith Allen, Port Chester’s First Black Asst HS Principal Understands The Assignment By Tatiana Pinheiro

  1. Patrick Swift // April 4, 2022 at 3:04 PM //

    Mr. Allen is not Port Chesters First African American Assistant Principal. Perhaps he is Port Chester High Schools, but Byron Womack worked with me as assistant principal from 2010 until his untimely passing in 2018. Mr. Allen is doing a fine job in his first year

    • I spoke to the author of the article, and this was her response, “I went to Port Chester High school and graduated in 2012. Mr. Wamack was not the principal there; he was the guidance counselor. He was my own guidance counselor before he passed. So, as a student I felt close to him.”

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