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Ann Walsh Henderson - Ann has been an attorney for the past 23 years. She specializes in appellate law. Ann graduated second in her class and with highest honors from the University of CT School of Law. While in law school, Ann served as Editor-in-Chief of the Law Review.  Following graduation, she did three federal clerkships, including clerking for Judge Thomas Meskill, then Chief Judge of the Second Circuit Court of Appeals and Judge Ellen Bree Burns, then Chief Judge of the Federal District Court of Connecticut. Ann also holds a Master’s degree in biochemistry. After completing her clerkships, Ann became an assistant professor at the University of CT School of Law before stopping to be a full-time homeschooling mom to her 4 children. Ann continued to work part-time in a law firm for over 13 years and then practiced as a solo practitioner.  She also taught Oral Argumentation as an adjunct professor at the law school.  Ann now runs Westfield Academy, a private debate, Model United Nations and leadership school. She also works as a consultant to the Connecticut Legislature when it is in session. Ann’s passion has always been helping people develop effective communication skills, both oral and written. She is especially committed to helping young people “Find Their Voices.”  Ann has been teaching oral advocacy classes to children of all ages since 2002.  She also developed and taught a summer debate program for gifted middle and high schoolers at Amherst College.  Ann is on the Board of the CT Middle School Debate League.

CurriculUM Design, Teacher And Coach

Jennifer Posner - Jen entered the world of debate in 2009 as a parent judge when her son began debating for St. Luke’s School in New Canaan, CT.  During the 2012-13 and 2013-14 school years she took on the role of volunteer coach at St. Luke’s and expanded the opportunities for students there, joining new leagues and creating a Middle School team. In 2014 she helped launch the CT Middle School Debate League, which she will direct for the 2015-16 school year. She has been working with Westfield Academy debaters since January 2015. Jen studied American History at Northwestern University and Public Policy at Harvard University’s John F. Kennedy School of Government. Because she has seen the tremendous benefits of competitive debate for her son, her daughter and their teammates, Jen is passionate about encouraging kids to debate, engaging them in the public policy issues of our time, and helping them to become engaged, informed, and communicative citizens. Jen also spends a lot of time doing and teaching yoga and traveling.

Advanced Debate Coach

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David Kimel - Westfield Academy is very excited to announce that the Coach of the award-winning Yale debate team, David Kimel, is returning this summer to the Westfield Summer Camp to teach a special program for Advanced Debate Students this summer.  David is about to get his PhD from Yale and has been the Head Coach of the Yale Debate Association from 2010-2015. Under his guidance, the team won First Place Club of the Year for all the years David has been coaching them. This summer at camp, David will teach an advanced program geared for experienced debaters who want to really focus on bringing their skills to the next level. This program will be appropriate for, although not limited to, juniors and seniors who are looking to make the transition to college debating. This is a rare and exciting opportunity!  Debaters who attended David’s classes last summer went on to win a number of debate tournaments this year including:  the International Public Policy Forum; the Loomis Debate Competition, Yale Osterweis and Northfield-Mount Hermon.Westfield Academy is very excited to announce that the Head Coach of the award-winning Yale debate team, David Kimel, is joining the Westfield Summer Camp to teach a special program for Advanced Debate Students this summer.  David has been the Head Coach of the Yale Debate Association from 2010-2015. Under his guidance, the team won First Place Club of the Year for all the years David has been coaching them. David graduated from Harvard, summa cum laude and was inducted into Phi Beta Kappa.  When he was a senior at Harvard, David received intercollegiate debate's highest honor being named the First Place team of the year.  He received the Howard Greenbaum Medal for speech and debate, Harvard's most prestigious prize for speech and debate. David is currently a PhD candidate in history at Yale and expects to receive his doctorate within the year.  In 2012-2013, he received the Yale Prize Teaching Fellow.

Debate Instructors

Rachel Alpert is a Sophomore at Wesleyan University and works as co-training director of their team. Her major is an interdisciplinary program in Government, Economics, Social Theory and History called the College of Social Studies. She is alum of Choate Rosemary Hall in Wallingford Connecticut, the former captain of their debate team, and former vice-President for the Model United Nations team. At Wesleyan, she works as a Jewish Renaissance Fellow, coordinating Jewish activities on campus. Outside of school and debate Rachel loves to run, read, and play squash.

Meghan Henderson - Meghan is a rising sophomore at Bates College. She has been debating with Westfield Academy since she was in fifth grade. Meghan won the State Middle School Debate competition twice and was recognized as the Best Middle School debater in the state. Last spring, Meghan made it to the semi-finals of the State High School Policy Debate Competition. Meghan has competed in numerous parliamentary and policy debate competitions including two international ones. Meghan has earned highest academic honors every semester in high school and recently won the Colletti Leadership Award in recognition of her leadership skills. Meghan is a two-sport varsity athlete and was Co-Captain of her Champion Varsity Soccer team. She has been selected twice to play on the New England All-Stars Soccer team and was named Most Valuable Offensive Player as a freshman. She was also chosen to be Captain of her Varsity Lacrosse team. Meghan is returning for her fourth year as a Program Assistant to Westfield Summer Camp.

Jeren Koh

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Alexa Wheeler is a senior at Wesleyan University and is the president of Wesleyan’s debate team. She is a Government and French double major and studied at Sciences Po in Paris during her junior spring semester. She is an alumna of Brooklyn Technical High School and was captain of the debate team as a senior and a quarterfinalist in the International Public Policy Forum as a junior. In addition to debate, she has tutored local elementary and middle school students in Middletown through Wesleyan’s Office of Community Service and now co-coordinates the tutoring partnership with Woodrow Wilson Middle School. Alexa interned at the Brooklyn District Attorney’s Office and at the New York State Division of Human Rights the last two summers. She will begin at NYU Law School in the fall.

Eliza Posner - Eliza Posner is a rising college freshman.  She will attend either Oxford or Northwestern in the fall. She has debated since freshman year and has been a captain of the the debate team since her sophomore year. Eliza's debate awards include winning first place varsity team at four Connecticut Debate Association tournaments, first place varsity speaker at three CDA tournaments, being a parliamentary semi finalist at the Yale Invitational Tournament, and being a parliamentary finalist as well as first place speaker at the UPenn Invitational Tournament.  This past year she qualified for and attended the Worlds Individual Debate and Public Speaking Championship in Hong Kong where she placed 20th.  She has been the top scholar (highest gpa) of her grade for the past two years and won the Brown University Book Award for best written and oral communicator this year. Outside of debate, Eliza enjoys riding horses and playing the guitar.

Madeleine Chill - Madeleine is a Sophomore at the University of Connecticut where she studies Spanish and Human Rights.  Previous to UConn, she spent three semesters at Manchester Community College where she achieved President's List every semester, was President of Alpha Mu Gamma (a foreign language honor society), and tutored other students in Spanish and ESL.  She debated with Westfield Academy for two years as a high-school-age homeschooler, and won several awards in Persuasive Speaking and Ethical Dilemmas.  She has been a writer since childhood, and was named Connecticut Youth State Poetry Champion in 2012.  She is deeply passionate about human rights, particularly food justice and queer issues.  In her spare time, she takes care of objectively too many houseplants and speaks broken Italian.

Debate, Model UN and Annex Instructor and Summer Camp Program Assistant

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Spencer Murray - Spencer is a rising senior at Hampshire College in Amherst. He is an alum of Kingswood Oxford School in West Hartford, Connecticut. His debating prowess has taken Spencer around the globe, to exotic locales such as Vancouver, Canada and Brisbane, Australia. In these competitions, his most prestigious accolades were the John Aimers Trophy for Top American speaker at the International Independent School Public Speaking Competition and the Second Place After Dinner Speech at the World Individual Debate and Public Speaking Championships. He served as Co-President of KO's Forensic Union. More recently, he has turned his gift of gab towards radio, co-hosting Paul Milligan’s Monkey Hour on Yurt Internet Radio. Spencer has been our Program Assistant at the Westfield Debate Camp for the past six years.

Annex Instructor and Summer Camp Leadership Director

Connor Henderson - Connor Henderson runs the Career Beginnings Office in Hartford Public High School for a local non-profit, where he works to improve college going outcomes for students from one of Hartford’s most underserved communities. Connor is a former CT homeschooler with a professional interest in education policy and the complex relationship between education and society. He graduated with high honors from the Georgetown School of Foreign Service, where he majored in Culture and Politics and was a member of the Parliamentary Debate Team. He has an academic background (and personal interest) in International Relations, Economics, Philosophy and History. In the last 5 years, he has taught more than ten writing, philosophy, economics and history classes through the Westfield Annex and the Great Books Program. Connor was also the creator of the Westfield Academy Leadership Program, which he offered to over 100 middle and high school students at the Summer Camp, and recently received a perfect score on the Verbal Reasoning section of the GRE. He runs a tutoring and college advising business, which focuses on writing skills, the humanities and college and scholarship essays and applications.


  • "Introduction to Political and Social Theory" 
  • "Introduction to the Analytical Essay" 
  • "Introduction to Global Justice"
  • "Why the West Got Rich: a History of Global Inequality and Development"
  • "American Character: Who we are, and why"

Annex Instructor and Summer Camp Advocacy Program Director

Teacher Bio: Caley Henderson is a Senior at Middlebury College, where she is majoring in Education: Privilege and Poverty (a self-designed major) and is minoring in Chinese Language and Literature. She has a 3.98 GPA. Caley is passionate about education and teaching and has significant experience doing what she loves. In the past five years, she has offered thirteen courses for homeschool students including classes in debate, art, literature and writing. For the past seven years, she has also been tutoring students of all ages in a variety of subjects including writing, English, math, history and SAT prep. She has been trained and certified as Middlebury College peer writing tutor.

Caley spent last spring studying Mandarin and education in Kunming, China. She then participated in a research internship with REAP (the Rural Education Action Program attached to Stanford University), conducting interviews and writing narratives for their website. She will continue to work with REAP in the coming semester, helping to research and write an upcoming academic paper. Prior to working with REAP, Caley has worked as an intern at the Connecticut State Department of Education; a curriculum developer and debate teacher at the Legacy Foundation of Hartford’s summer program for underserved students; and the designer and director of the Advocacy Elective Program at the Westfield Academy of Debate, Model United Nations and Leadership Summer Program.

While at school, Caley loves to debate. She has served as the President of Middlebury’s Debate Society and has won several speaking awards in her time at college, including Novice Champion at Dartmouth, and has been selected to compete at the the World Universities Debating Championships, the Pan-American British Parliamentary Championship and American Parliamentary Debate Nationals. In addition to debating, Caley also leads the Middlebury Student Quaker group on campus and is committed to service work. She is a weekly volunteer at The Charter House, a local warming shelter and a transitional housing organization, and previously sat on the Board of Directors of an established Addison county non-profit called HOPE (Helping Overcome Poverty’s Effects).

Caley has always loved Irish dancing, making art, hiking, reading and especially writing. Most importantly, Caley truly loves teaching writing and is very excited to read the wonderful works that you will all create!


  • Analytical Writing and Literature
  • Introduction to Debate
  • Art Survey Course
  • Creative Writing