2021 Teen Diversity Essay Contest
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In order to increase awareness and promote understanding in the arenas of race, ethnicity, religion, gender, sexual orientation, and gender-identity, TEAM Westport and The Westport Library are co-sponsoring the Eighth Annual Teen Diversity Essay Contest for students in grades 9, 10, 11, and 12 who attend Staples High School or another school in Westport, or reside in Westport and attend school elsewhere. Last year’s TEAM Westport contest focused on stereotypes. This year’s challenge asks you to focus on “Black Lives Matter”.
2021 Essay Challenge Prompt
“The statement “Black Lives Matter” has become politicized in our country. In 1000 words or fewer, describe your own understanding of the statement. Consider why conversations about race are often so emotionally charged. Given that reality, what suggestions do you have for building both equity and equality in our schools, community and country?”
2021 Essay Process
Click here for Contest Application. [PDF]
Winners have been announced at a ceremony at the Westport Library on April 5, 2021. At the discretion of the judges up to three cash prizes have been awarded subject to the volume and caliber of entries received. The first prize is $1,000, second prize is $750, and third prize is $500.
FIRST PLACE: Max Tanksley with "Words of Power"
SECOND PLACE: Curtis Sullivan with "Black Lives Can Matter More. Here's How."
THIRD PLACE: Jaden Mello with "Responsibility of a Nation"
2020 Essay Contest
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TEAM Westport, in partnership with The Westport Library and the Town of Westport announced the winners of the Seventh Annual Teen Diversity Essay Contest on Thursday, August 13 at 7:00 pm. All winners were Staples students at the time of contest entry. The Awards Ceremony had been postponed in March from its original April 2 date due to the COVID crisis.
Sahiba Dhinsa was named the First Place essayist and awarded $1,000 for her work entitled “STEREOTYPES, STORIES, AND THE WORLDS WE CREATE”. Sahiba is a Staples graduate who plans to attend Cornell.
Sahiba Dhindsa - Stereotypes, Stories, and the Worlds We Create
Zachary Terrilion was named Second Place essayist and $750 for his work entitled
“ STEREOTYPES: CRIPPLING STANDARDS ”. Zachary is a Staples graduate who plans to attend Oberlin.
Terrillion - Stereotypes Essay
Victoria Holoubek-Sebok was named Third Place essayist and awarded $500 for her work entitled “BOMBSHELL”. Victoria is a rising junior at Staples.
Victoria Holoubek-Sebok - Bombshell
First Selectman Jim Marpe congratulated the essayists for their “equally moving and personal” works which “were not just some abstract discussions of concept but very personalized views as they applied to their lives”.
BIll Harmer, Executive Director of Westport Library welcomed the essayists and congratulated them all for their “well documented, clearly thought out and carefully written” essays.
TEAM Westport Chair Harold Bailey reminded the finalists that “they are now part of a long tradition of not only beautifully written works but works that really make a difference in the way that the town operates”.
Susan Ellis, TEAM Westport Essay Committee Chair and Dr. Judith Hamer, Chief Judge of Essay Evaluation also commended the essayists as they explained the objectives and processes under which the Essay Contest was conducted.
While the ceremony was staged with limited participation at the Library, it was webcasted as a virtual event to the Westport community. It may currently be watched at
https://www.crowdcast.io/e/team-westport-teen
In order to increase awareness and promote understanding in the arenas of race, ethnicity, religion, LGBTQ, and gender-presentation, the Annual Teen Diversity Essay Contest is open to students in grades 9, 10, 11, and 12 who attend Staples High School or another school in Westport, or reside in Westport and attend school elsewhere.
2019 Essay Contest
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Congratulations to the Winners of this 2019's TEAM Westport Essay Contest!
First place winner, Chet Ellis, receiving his award from Harold Bailey, Jr. and First Selectman, Jim Marpe.
Read first place essay, by Chet Ellis, "The Sound of Silence"
Second place winner, Angela Ji receiving her award from Harold Bailey, Jr. and First Selectman, Jim Marpe.
Third place winner, Daniel Boccardo, receiving his award from Harold Bailey, Jr. and First Selectman, Jim Marpe.
Read third place essay, by Daniel Boccardo, "Cactus In A Rainforest"
Olivia Sarno receiving the honorable mention award from Harold Bailey, Jr. and First Selectman, Jim Marpe.
Read Honorable Mention essay, by Olivia Sarno, "Deconstructing The Voice Inside My Head"
The winners of the 6th annual TEAM Westport Teen Diversity Essay contest were announced at a ceremony on April 3, 2019 at the Saugatuck Congregational Church in Westport. The annual Essay contest is a joint project with The Westport Library and challenges local students to explore timely social topics about race, ethnicity and identity.
Regarding the Contest, First Selectman Jim Marpe stated, “In just a few short years, the TEAM Westport essay contest and its thought-provoking topics has become an integral part of community life for teens in our town. It’s a great complement to the excellent educational offerings we enjoy here. We look forward to continued focus on these important issues in partnership with TEAM Westport, the Westport Library, and local educators.”
Each year, a different topic area is posed as a challenge to potential entrants. This year’s Essay Challenge was ‘Micro-Aggressions’. Harold Bailey, TEAM Westport’s chair since its founding, says, “TEAM Westport’s focus is making Westport increasingly welcoming regarding race, religion, ethnicity and identity. By far, the largest, most pervasive hurdles we face in achieving that mission are the ongoing micro-aggressions faced by citizens, visitors and non-Westport employees in each arena. This year’s challenge provides an opportunity to delve into this problem area as well as potential solutions to address it.”
Open to high school students who either attend school in Westport or live in town and attend school elsewhere, this year’s contest boasted three winners and an honorable mention from students all attending Westport’s own Staples High school. Essays are reviewed by a panel of judges from the community and include civil rights activists, professional journalists, librarians and educators. “We were very impressed this year with the depth of experience and quality of writing among the winning essays,” said Dr. Judith Hamer, the Head Judge who chairs the Essay Contest Committee’s Evaluation sub-committee for TEAM Westport.
This year’s winners included:
Chet Ellis, a senior at Staples High School, won First Place and $1,000 for his essay entitled The Sounds of Silence which addressed how people of color often feel pressured not to call out microaggressions and therefore, potentially abet them.
Angela Ji, a senior at Staples High School, won Second Place and $750 for her essay Ripping Off the Bandaid: Microaggressions and How We Address Them which discussed the cumulative wound that the constant “finger pricks” of microaggressions can cause.
Daniel Boccardo, another Staples High School senior’s essay Cactus In A Rain Forest won Third Place and $500. That essay discussed ingrained social constructs of “us” and “them” that are the foundation for microaggressions against marginalized groups, particularly immigrants.
An Honorable Mention went to Staples High School junior, Olivia Sarno, who wrote about microaggressions against LGBTQ students in her essay, Deconstructing The Voice Inside My Head.
Overall the winning essays are brilliant, courageous and powerful. And while some might find them strictly disturbing or disheartening, Harold Bailey framed their impact as both a caution and an opportunity. The caution was to call attention to this ongoing dynamic in our schools which is common to most public schools nationwide with our demographics. The opportunity was to work together as a community to address it. TEAM Westport is committed to helping move that process forward.
Individuals or organizations who would like to participate in sponsorship of next year’s contest are invited to contribute via the website ( www.teamwestport.org ) or by contacting TEAM Westport via info@teamwestport.org. All contributions are deductible to the extent permitted by law.
The winners of the 6th annual TEAM Westport Teen Diversity Essay contest were announced at a ceremony on April 3, 2019 at the Saugatuck Congregational Church in Westport. The annual Essay contest is a joint project with The Westport Library and challenges local students to explore timely social topics about race, ethnicity and identity.
Regarding the Contest, First Selectman Jim Marpe stated, “In just a few short years, the TEAM Westport essay contest and its thought-provoking topics has become an integral part of community life for teens in our town. It’s a great complement to the excellent educational offerings we enjoy here. We look forward to continued focus on these important issues in partnership with TEAM Westport, the Westport Library, and local educators.”
Each year, a different topic area is posed as a challenge to potential entrants. This year’s Essay Challenge was ‘Micro-Aggressions’. Harold Bailey, TEAM Westport’s chair since its founding, says, “TEAM Westport’s focus is making Westport increasingly welcoming regarding race, religion, ethnicity and identity. By far, the largest, most pervasive hurdles we face in achieving that mission are the ongoing micro-aggressions faced by citizens, visitors and non-Westport employees in each arena. This year’s challenge provides an opportunity to delve into this problem area as well as potential solutions to address it.”
Open to high school students who either attend school in Westport or live in town and attend school elsewhere, this year’s contest boasted three winners and an honorable mention from students all attending Westport’s own Staples High school. Essays are reviewed by a panel of judges from the community and include civil rights activists, professional journalists, librarians and educators. “We were very impressed this year with the depth of experience and quality of writing among the winning essays,” said Dr. Judith Hamer, the Head Judge who chairs the Essay Contest Committee’s Evaluation sub-committee for TEAM Westport.
This year’s winners included:
Chet Ellis, a senior at Staples High School, won First Place and $1,000 for his essay entitled The Sounds of Silence which addressed how people of color often feel pressured not to call out microaggressions and therefore, potentially abet them.
Angela Ji, a senior at Staples High School, won Second Place and $750 for her essay Ripping Off the Bandaid: Microaggressions and How We Address Them which discussed the cumulative wound that the constant “finger pricks” of microaggressions can cause.
Daniel Boccardo, another Staples High School senior’s essay Cactus In A Rain Forest won Third Place and $500. That essay discussed ingrained social constructs of “us” and “them” that are the foundation for microaggressions against marginalized groups, particularly immigrants.
An Honorable Mention went to Staples High School junior, Olivia Sarno, who wrote about microaggressions against LGBTQ students in her essay, Deconstructing The Voice Inside My Head.
Overall the winning essays are brilliant, courageous and powerful. And while some might find them strictly disturbing or disheartening, Harold Bailey framed their impact as both a caution and an opportunity. The caution was to call attention to this ongoing dynamic in our schools which is common to most public schools nationwide with our demographics. The opportunity was to work together as a community to address it. TEAM Westport is committed to helping move that process forward.
Individuals or organizations who would like to participate in sponsorship of next year’s contest are invited to contribute via the website ( www.teamwestport.org ) or by contacting TEAM Westport via info@teamwestport.org. All contributions are deductible to the extent permitted by law.
Teen Diversity Essay Contest 2018
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As the nation continues its historic social shifts relating to race, ethnicity, religion and identity, young people have a great deal to absorb and consider regarding the evolving different America. In order to increase awareness and promote understanding in this arena, TEAM Westport and The Westport Library are co-sponsoring the fifth annual Teen Diversity Essay Contest for students in grades 9, 10, 11, and 12 who attend Staples High School or another school in Westport, or reside in Westport and attend school elsewhere.
Essay Topic:
The focus of this fifth essay contest is the issue of 'appropriate protest’ which has surfaced recently as a topic of significant national controversy. This year’s invitation states, “Recently several professional athletes have “taken a knee” during the singing of “The Star-Spangled Banner” to bring attention to--and to protest—ongoing bias and discriminatory practices in American society in general and by law enforcement officers in particular. In reaction, some people have called these athletes “unpatriotic.” In 1,000 words or fewer, describe your understanding of what it means to be a patriot, what kinds of behavior you think would be unpatriotic, and what forms of protest against discriminatory laws, customs, or patterns of behavior you would consider legitimate."
Essay Process
Click here for Contest Application. [PDF]
Essays are due no later than Feb. 27, 2018. Winners will be announced at a ceremony at the Westport Library on April 2, 2018. Subject to the volume and caliber of entries received, at the discretion of the judges up to three prizes will be awarded. The first prize is $1,000, the second is $750, and the third prize is $500.
2017 Essay Contest
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2017 Essay, Chet Ellis, 1st place
2016 Essay Contest
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The winners (L-R) were Ellie Shapiro (Staples HS), 2nd place; Ali Tritschler (Green's Farms Academy), 3rd place and Jacob Klegar (Choate Rosemary Hall), 1st place for the second year in a row. Harold Bailey (far L), Chair of TEAM Westport and First Selectman Jim Marpe (far R) were present to honor the winners.
Three students—one each from Choate Rosemary Hall, Staples High School, and Green Farms Academy—have won TEAM Westport’s Teen Diversity Essay Contest, which is co-sponsored with the Westport Library. The annual contest is open to high school students who reside in Westport or who attend school in Westport. In light of the many recent demonstrations in cities and on college campuses, this year’s contest asked students to consider the state of race relations in our country, “both the nature of the problem and the appropriate way to address divisions and inequities in our society.”
First prize winner for the second year in a row is Jacob Klegar, now a senior at Choate Rosemary Hall. In his essay “The Black Lives Matter Movement: Past, Present, and Future” Jacob advocated focusing on our nation’s youth, particularly on putting them in “actual diverse environments from a young age.” He noted that “one of the biggest obstacles to solving our America’s race problem is the segregation of black and white communities…” Jacob also advocated promoting open dialogue among high school and college students as a way to help students understand each other’s opinions—provided all opinions were welcome and listened to. Jacob’s prize is $1,000.
Second prize winner is Ellie Shapiro, a student at Staples high School. Elli’s essay, "Coming to Terms with Race in America" is a personal reflection on her own journey as she has faced the privileges afforded her as a white person living in an affluent community, struggled to understand the realities of African American lives, and continually works to acknowledge and combat her own racism. Ellie’s prize is $750.
Third prize winner is Ali Tritschler, a student at Greens Farms Academy. She, too, described her personal journey toward understanding her own position of privilege, the discrimination experienced by African Americans, and the causes of the many demonstrations that have occurred recently protesting police actions as well other forms of discrimination. Her essay is "Awareness". Ali’s prize is $500.
The prize winners read their essays on Monday, May 16, at the Awards Ceremony in the Westport Library McManus room. Jim Marpe, Westport’s First Selectman, and William Harmer, Director of the Westport Library, were present to honor the winners. Harold Bailey, TEAM Westport’s Chair since its founding in 2004, presented the prizes.
Bailey says, “ TEAM Westport and the Library co-sponsor this annual contest in order to help focus Westport teenagers on the challenges facing our increasingly diverse society and to encourage them to think seriously about their own potential role in making our society both welcome and value the diversity of its citizens.”
Additional photos of the awards event may be seen at the Team Westport Facebook Page.
2015 Essay Contest
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Pictured are (l-r) Maxine Bleiweis, director of the Westport Library; Selectman Avi Kaner; Brendan Massoud, second place winner; Jacob Klegar, first place winner; Harold Bailey, head of TEAM Westport, and Teri Walsh, president of Sachs Walsh Insurance, the event sponsor.
Two students have won TEAM Westport’s 2015 Teen Diversity Essay Contest co-partnered with the Westport Library and sponsored by Sachs Walsh insurance. The contest was open to all high school students who are residents of Westport or attend school in the town. The winning essays may be downloaded at the links below.
Jacob Klegar, a Westport resident and junior at Choate Rosemary Hall School, has won first prize in the contest. His essay entitled ”Friendship Through a Shared Love of Tennis [PDF]” explores the premise that the key to breaking down “self-segregation” in the cafeteria is for schools to put “a greater emphasis on clubs, sports, and other extracurricular activities and encouraging others to get involved with their passions” in an environment in which “interracial friendships are encouraged and valued at least as much as intraracial ones”. He mentions pragmatic lessons which could be learned from Choate’s “progress in fostering diversity” by “American schools more generally …including Westport, which is over 90 percent Caucasian”. After acknowledging that “boarding schools” like Choate “have the luxury” of “admitting a diverse student body” , he challenges them to take on the “deeper, tougher issues that remain” and makes suggestions for their doing so. Ultimately, for boarding schools, he states that success should not be measured by “ the admissions department” enrolling “a multicultural freshman class, but when, sophomore year, a Chinese National and black student from Nigeria decide to room together [as] best friends through a shared love of tennis”. Jacob’s prize was $1,000.
The second prize winner is Brendan Massoud, a sophomore at Staples High School. His essay, entitled “Eat and Meet [PDF]”, frames the cafeteria issue by positing, “…people are comfortable with people who are easy to identify as being similar” and there is a“…common perception that people of our same race act and communicate the same way we do”. “...So while the cafeteria should be a place where students …feel comfortable familiarizing themselves with others from varying backgrounds and with different experiences and viewpoints, it instead becomes a place of self-division based on those very differences.” Brendan uses personal examples to demonstrate why this might happen and how one might move beyond such “self-division”. He, then, offers a “very plausible school-wide solution [for Staples] that would familiarize people with each other” based upon grouping students “one day a week” by “the period and class during which lunch takes place”. Overall, he states , “I see it as crucial that Staples students become more familiar with the different races, ethnicities, sexual orientations, and interests that span the student body, in order to increase friendliness and interaction among them, to maximize the value of the Staples education, and to make Staples graduates more productive members of society.” Brendan’s prize was $750.
The prize winners read their essays on Monday, April 6, at the Awards Ceremony in the Westport Library's McManus Room. Avi Kaner, Westport’s second selectman; Maxine Bleiweiss, Executive Director of the Westport Library; and Teri Walsh, President of contest sponsor sachs Walsh Insurance were present to honor the winners. Harold Bailey, TEAM Westport’s Chair, presented the prizes.
The topic for this second essay contest is based on the reality that the school cafeteria is often a setting in which students self-segregate. The guidelines for entrants say, “Please reflect on the barriers that prevent students from reaching out to others who are different from themselves, particularly those who are of a different race, ethnicity, and/or sexual orientation.”
Co-partnered by TEAM Westport and the Westport Library, the contest asked teens to reflect on the barriers that prevent students from reaching out to others who are different from themselves, particularly those who are of a different race, ethnicity, and/or sexual orientation. Specifically the contest asked students to “describe those barriers, and identify specific steps you and other students in your high school can take to help students break down those barriers—especially in the cafeteria. Indicate what you believe are the risks and benefits of making that effort.”
Judges for the essay contest were Patricia Wei, of Yale University; grant writer and educator Judith A. Hamer, Ph.D., ; and the Westport Library's Teen Services Librarian Jaina Lewis.
Bailey, TEAM Westport’s chair since its founding in 2004, says, “ Initiatives such as this essay contest are key vehicles for enabling Westport students to focus on key issues of diversity in the world surrounding Westport. This year’s Essay Topic – ‘The Cafeteria Challenge’ -was a very demanding one. While the school cafeteria is the most obvious place to meet new people from backgrounds and social groups outside a student’s own, it is also the place most fraught with personal vulnerability for doing so. Framing such a level of complexity while offering pragmatic remedies to resolve it in 1,000 words or less of high caliber writing is a very tall order. We applaud the insight, skill and courage of the award winners.”
TEAM Westport has developed a unique role in the community. By partnering with municipal, government and community institutions it draws attention to issues around multiculturalism and diversity, making the invisible, visible. Examples include co-sponsoring diversity focused programming with The Westport Library, working with Westport Schools and its Board of Education on diversity, assisting in diversity recruiting and training with the town’s police and fire departments, scheduling “talk-back” sessions on issues raised by performances at the Westport Country Playhouse and participating in initiatives with the community’s Interfaith Council.
2014 Essay Contest
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Megan Root, Eliza Llewellyn and Kyle Baer Awarded Prizes in TEAM Westport
Three students from Staples High School won TEAM Westport’s Teen Diversity Essay Contest, open to all high school students who are residents of Westport or attend school in the town.
Megan Root, a junior at Staples High School, has won first prize in the contest. Her essay with the title, “Diversity: the Maestro of Innovation” explores what she is missing by being in a community that is 93% white. “I think Staples’ classes present a lot of the right questions, but the dearth of diversity means there are perspectives I’ve never heard,” she writes. She looks forward to being exposed to more diversity as the U.S. population changes and as she is in new environments. “I don’t think I can really complete an education in life until I join bigger, more varied conversations. America’s diversity means access to cultures and traditions and ideas from every corner of the globe,” Megan says. Megan’s prize was $1000.
The second prize winner was Eliza Llewellyn, Staples senior and the valedictorian of her class. Her essay is titled “No Longer 91 Percent.” She begins her essay by saying she grew up in a “family whose ancestry was flanked by dragons: the crimson Welsh ddraig goch and the scaly Chinese long.” She reflects on her experience in Westport and how differences are sometimes regarded negatively. Nonetheless she has hope for her own and America’s future. “Beyond economic strength, a mix of ethnicities will make us more tolerant and empathetic towards others. Rather than recoiling from a gay couple or crossing to the other side of a street from a black man in a hoodie, we can learn to see these individuals as people rather than a blanketed ‘other’,” Eliza says. Eliza took home a prize of $750.
Third prize essayist Kyle Baer, a junior at Staples, was less optimistic. He entitled his essay, “Westport: A Bubble Refuses to Pop.” Kyle described his classes at Staples and his experience in town as almost entirely Caucasian. “This racial inequality sets Westport back from the rest of the nation in terms of its cultural richness.” He says. “To be stuck in an upper-class, all-white town in the coming years will be a significant disadvantage to students. We have little choice but to evolve, or risk losing our appeal as a family-friendly town. Yet the path on which Westport is headed shows, as of yet, no signs of diverging.” Kyle won a prize of $500.
The three prize winners read their essays on Monday, March 31, at the Awards Ceremony in the Westport Library's McManus Room. Jim Marpe, Westport’s first selectman, was present to honor the winners. Harold Bailey, TEAM Westport’s chair, presented the prizes.
Co-sponsored by TEAM Westport and the Westport Library, the contest asked teens to reflect on the impact of changes in U.S. demographics with the expectation that racial and ethnic groups that are currently in the minority in our country will collectively outnumber whites within thirty years. Specifically the contest asked students to “describe what you think are the benefits and challenges of this change for Westport and for you, personally.”
Judges for the essay contest were grant writer and educator Judith A. Hamer, Ph.D.; Jaina Lewis, Westport Library Teen Services Librarian; and Patricia Wei, of Yale University.
Bailey, TEAM Westport’s chair since its founding in 2004, says, “This contest gave high school students a chance to talk about the impact our nation’s rapidly changing racial and ethnic make-up will have on their own lives. I was impressed with the quality of the twenty five essays we received.”
TEAM Westport has developed a unique role in the community. By partnering with municipal, government and community institutions it draws attention to issues around multiculturalism and diversity, making the invisible, visible. Examples include co-sponsoring diversity focused programming with The Westport Library, working with Westport Schools and its Board of Education on diversity, assisting in diversity recruiting and training with the town’s police and fire departments, scheduling “talk-back” sessions on issues raised by performances at the Westport Country Playhouse and participating in meetings with the community’s Interfaith Council.
The Essay Topic is reprinted below:
“According to the US Census, 30 years from now racial and ethnic groups that are currently in the minority in our country will collectively outnumber whites. That change has already occurred for people aged 20 and younger—a group in which the total minority population now outnumbers whites.
"As a high school student in 2013-14, you and your contemporaries are already part of this new realty. Please reflect on the impact this demographic trend will have on our country and on your life.
"In 1000 words or less, describe what you think are the benefits and challenges of this change for Westport and for you, personally.”