Winners of this year’s Teen Diversity Essay Contest are, from left, Annam Olasewere, first place; Aanya Gandhi, second; Sienna Tzou, honorable mention, and Souleye Kebe, third. / Contributed photos

By John Schwing

WESTPORT — In a town where in the last year racist and antisemitic bullying in schools has been called out, violent and offensive videos circulated online and a Hitler snowman was built in a woodland preserve, the issue of “Identity” — defined in personal and communal terms of acceptance — could not be more timely.

Four young Westporters with thoughtful ideas about that complicated, often controversial, issue were honored this week as winners in the annual “Teen Diversity Essay Contest,” co-sponsored by TEAM Westport and the Westport Library.

The 12th annual contest, open to entries from high school students, challenged essayists to examine the issue of identity from several perspectives — their own; how identity shapes their interactions in and outside of school, and steps they advocate to end identity-based bias, bullying and hate.

The winners, all Staples High School students, were named at a ceremony Monday at the Westport Library. (A video of the ceremony can be viewed on the library’s YouTube channel by clicking here.) The winners are:

Annam Olasewere, a senior and co-chair of the town’s Youth Commission, won the $1,000 first prize for her essay, “Understood. Connected. Valued.”

In an excerpt from her essay, she writes: 

Westport prides itself on being a welcoming community, but belonging is not just about physically being in a space with others — it’s about being understood. It’s about being connected to your community. It’s about being valued. 

While I’ve never been directly told, “You don’t belong here,” I’ve felt it in a thousand quiet ways — the double takes when I say Westport is my hometown, the disbelief when I step into leadership roles or excel in AP courses, or the doubt people show when I pursue activities outside the norm for “someone like me.” It’s not outright hate; it’s something more subtle yet just as isolating — a quiet bias that makes me feel like I must constantly prove my worth.

Her full essay is attached to the end of this article.

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Aanya Gandhi, a sophomore, was awarded the $750 second prize for her essay, “White Paint and Other Lies.”

An excerpt from her essay follows:

Moving to Westport was like stepping into a world that had already written its script.

Individuality was celebrated, but only in its most polished form-never raw, never messy. There was a right way to be unique, a right way to be different. I learned early on that there were two versions of myself: the one that fit and the one that didn’t. The one that could blend seamlessly into the rhythm of this town, and the one that pulsed just slightly offbeat.

Being a “hyphenated American” means existing in the space between the lines. It means translating parts of yourself depending on the audience, slipping between languages, between customs, between ways of thinking. Jt means carrying the weight of two histories at once, even when the world only asks for one. In Westport, I have felt this duality in ways I never had before.

Her full essay is attached to the end of this article.

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Souleye Kebe, a junior and student representative to the Board of Education, received $500 for his third-place essay, “S-L-M.”

The following is excerpted from his essay: 

Being born an African, I had to come to terms early on that people who look like me haven’t had a historically positive relationship with the United States. What made it easier was that I didn’t have to accept that by myself, because I lived in New York City where everybody came from diverse backgrounds, many of them having similarly complex relationships with the country we were born in. 

Coming to Westport was admittedly a culture shock, since I had never seen so many people with such relative conformity. The students here had the same clothes, same style of speaking, and same style of general being. 

They also shared the same statements: requests like, ”Can I touch your hair?” remarks such as, “I don’t see color;” and “boasts” like, “I had a Black friend in elementary school.” 

I thought that these words were nothing more than stories, and so I was astonished to hear people say them to my face. Through that, I remained Souleye Kebe, an African from New York City.

His full essay is attached to the end of this article.

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Sienna Tzou, a freshman, received honorable mention and $250 for her essay, “The Value of Identity from the Start.”

She writes in an excerpt from her essay:

I saw that some of my classmates snickered and very audibly attempted to imitate how I spoke. Others whispered and pointed their fingers at me, as if my Asian “exoticism” was a foreign contaminant that could somehow infect the class.

For the next two years, I made a silent resolve to avoid socializing altogether. I didn’t want kids mimicking how I spoke, and it gave me the excuse to not be obligated to answer the unfiltered questions I knew everyone wanted to ask me.

By the third grade, groups of girls were impersonating me by blabbering gibberish as my Mandarin, and pulling at the corners of their eyes behind my back.

Thus, I forced a stoic, protective facade over my true identity, shrinking back into a silent reticence of social evasion.

Her full essay is attached to the end of this article.

Joining winners of the 2025 Teen Diversity Essay Contest, announced Monday at a Westport Library ceremony, were from left, First Selectwoman Jennifer Tooker, Westport Library Executive Director William Harmer, contest winners Annam Olasewere, Aanya Gandhi, Sienna Tzou and Souleye Kebe, Staples High School Principal Stafford Thomas and Harold Bailey Jr., chair of TEAM Westport. 

Award-winning essayists lauded

“Identity is at the core of who we are and what we allow ourselves to become,” Harold Bailey Jr., the chair of TEAM Westport, the town’s diversity and multi-cultural advocacy committee, said in a statement to the Westport Journal.

“There is a great deal for all of us to glean to  from these brilliant young voices,” he added.

The Westport Library “is once again proud to host this celebration of young voices addressing crucial issues of identity and inclusion,” William Harmer, the library’s executive director, said in a statement issued by the library.

“These essays are powerful and thoughtful. They demonstrate the great diversity of the Westport experience and reflect the library’s mission to empower individuals and strengthen the community through learning and the open exchange of ideas.”

One of the contest judges this year was Shonda Rhimes, the noted screenwriter, television producer and Westport resident.

“As a writer, I know how important having outlets of expression can be,” Rhimes said in the library’s statement announcing the winners. 

“The TEAM Westport essay contest provides our young people with the opportunity to raise their voices and be heard while also showcasing the rich diversity of thought so necessary for fostering community,” she said.

John Schwing, consulting editor of the Westport Journal, has held senior editorial and writing posts at southwestern Connecticut media outlets for four decades. Learn more about us here.

Following are complete texts of the four winning essays: