Southold graduates urged to keep learning, embrace failure
The 2026 Southold Junior-Senior High School senior class turned its tassels and tossed its caps into the air Saturday afternoon, trading the familiarity of high school for the uncertainty — and excitement — of whatever comes next.
The ceremony mixed humor with heartfelt advice as student speakers reflected on the journey that brought them to graduation and school leaders encouraged the Class of 2026 to embrace the future ahead.
Salutatorian Nathan Steinfeld, who plans to attend Vanderbilt University and pursue a career in comedy and filmmaking, had classmates, teachers and families laughing throughout his address.
“I once emailed an assignment at 2:58 a.m. to one of my teachers and he replied at 3:11 a.m. saying, ‘Got it, thanks,'” Nathan quipped. “The next day, he asked me why I was up at 2:58 in the morning. I replied, ‘Why were you up at 3:11 in the morning?'”
The light-hearted speech continued as Nathan also poked fun at his academic standing.
“Second place is the first loser, so technically I’m first at something,” he said, referring to earning the title of salutatorian.
The jokes gave way to a more serious conclusion as Nathan closed with a quote from the speech delivered by coach Herb Brooks before the United States men’s hockey team’s historic upset over the Soviet Union in Miracle, urging his classmates to believe in themselves as they begin the next chapter. He likened the graduating class to a hockey team, calling on them to trust one another and rise to the moment.
Valedictorian Elizabeth Estrada reminded graduates that while their high school education had come to an end, their pursuit of knowledge should not.
“Today is not the end of our education,” Elizabeth said. “It’s an invitation to continue learning. Let’s never become too busy or too indifferent to ask questions. And let’s never feel we’re too grown up to experience wonder again. One question a day, and remembering the answer, can change how you move through life and the relationships you form with those around you.”
Superintendent Dr. Anthony Mauro reinforced that message by reminding graduates that success is often built on failure. He pointed to Major League Baseball Hall of Famer Ty Cobb, whose .366 career batting average still meant he failed to record a hit nearly two-thirds of the time he stepped to the plate.
“Ty Cobb batted .366 for his career,” Dr. Mauro said. “That means almost two-thirds of the time he came to the plate, he got out. What he did do was continue to move forward. Never be afraid of failure. Embrace it, learn from it, let it motivate you and work harder to move forward in life.”
Dr. Mauro also reminded graduates that there is no single roadmap to success.
“You may know precisely what you want to do for the rest of your life, or you may try many different things before you find your true calling,” he said. “All of these paths are good paths. … No matter what you choose, you will encounter hardships. There is great strength in knowing what you need help with and asking for it. … Don’t ever think you can go without the support and love of the people who care about you.”
As the ceremony concluded and the graduates celebrated with family and friends, the Class of 2026 left Southold High School with diplomas in hand and a common message echoing from the stage: keep learning, embrace failure and never stop believing in what comes next.
Portraits of Achievement
Elizabeth Estrada
Valedictorian
GPA:102.82 (weighted)
College: Stanford University
Major: Mechanical engineering
Elizabeth has been a standout leader and innovator throughout her time at Southold High School. As president of the National Honor Society and captain of the FIRST Robotics Team R.I.C.E. 870, she led her peers to regional success and earned the General Motors Industrial Design Award.
Elizabeth’s diverse talents include serving as concertmaster for the Chamber Ensemble and vice president of the Student Council, alongside 200-plus hours of service teaching 3D printing and coding at CAST. She also served as president of International Club and editor of the Southold Sentinel newspaper.
She will continue her education at Stanford University, where she plans to study mechanical engineering with a focus on medical devices.
SALUTATORIAN
GPA: 101.28
College: Vanderbilt University
Major: Cinema and media arts
Nathan is a High Honor Roll scholar/athlete who has seamlessly blended excellence with creative and entrepreneurial drive. In athletics, Nathan was a soccer all-county scholar athlete, received the varsity lacrosse coaches award and was senior captain of the lacrosse team he played with all four years in Southold. He performed as a gifted musician in the Jazz Ensemble and HMEA Honor Band.
Nathan also distinguished himself as an award-winning filmmaker, serving as lead comedy writer for SOHO TV and senior chair of the Film Club. Beyond his creative pursuits, he is a proven businessman and a dedicated community volunteer at CAST and the North Fork Arts Center. Nathan will attend Vanderbilt University this fall where he looks forward to studying Cinema and Media Arts.
Scenes from commencement
Photos by Nick Mongiovi
Southold Awards and Honors
Connie Benson – New York State Academic Excellence Awards, Rank 3; Richard & Marion Pierson Memorial Scholarship; Katherine S. Leavay Memorial Scholarship; Helen S. Wurth Memorial Scholarship Fund – Excellence in Social Studies; Helen S. Wurth Memorial Scholarship Fund – Excellence in English; Southold Free Library Scholarship; Southold S.C.O.P.E. Education Services Scholarship; St. Peter’s Lutheran Church Scholarship; North Fork Breast Health Coalition; Office of the State Comptroller, Thomas P. DiNapoli Student Achievement Award; Office of the New York State Attorney General, Letitia James – Triple “C” Award; Southold High School Principal’s Award; William J. McGonegal Memorial Humanitarian Award.
Emma Binkis – Rotary Club of Southold in Memory of Jere Jacobs – Performing Arts Scholarship.
Shaun Bumble Jr. – Roman J. Wilinski Memorial Scholarship.
Robert Campos Velasquez – Southold Fire Department, Packard Hose Vocational Scholarship; Special Education Administrators of Suffolk (S.E.A.S.).
Corinna Carbajal – Victoria Makakis Memorial Scholarship; Mattituck Lions Club, Kaitlyn Doorhy Strawberry Queen Memorial Scholarship; Southold Town Police Benevolent Association (PBA) Scholarship.
Marangely Carreto Gutierrez – Rotary Club of Southold English Language Learner Scholarship.
Collin Cornell – Southold School Athletic Association; Southold Town Police Benevolent Association (PBA) Scholarship.
Evan Czartosieski – Richard M. Osmer Memorial Sports Fund Awards; Southold School Athletic Association.
Lila Dailey – Rotary Club of Southold Interact Scholarship.
Brendan Domaleski – Suffolk Association of School Business Officials Award (SASBO).
Elizabeth Estrada – Valedictorian Award; New York State Academic Excellence Awards, Rank 1; William J. McGonegal Memorial Award; Zaveski Lucey Memorial Foundation Award; Elks Most Valuable Student; North Fork Women, Anne MacKay Memorial Scholarship; Helen S. Wurth Memorial Scholarship Fund – Excellence in Science; Helen S. Wurth Memorial Scholarship Fund – Excellence in Mathematics; Rotary Club of Southold, Paulette Ofrias Memorial Community Service Award; Southold Music Boosters Scholarship; Southold Free Library Scholarship; Southold PTA Student Award; Suffolk Times Journalism Award; Suffolk County Music Educators Association (SCMEA) Scholarship; Southold Town Republican Club Award; Suffolk County Highway Superintendents Association Scholarship; National School Development Council (NSDC) Award for Academic Growth & Student Leadership in Learning; LEAD LI, Ira Schwartz Scholarship.
Caroline Fannon – Dominick Giovanniello Sr. Memorial Scholarship; New Suffolk S.C.O.P.E. Education Services Scholarship; Dylan Newman Forever 5 Foundation Scholarship; Cutchogue Fire Department – Grant for Higher Education in Memory of Stanley L. Victoria & Wayne Glover.
Angel Garza – Southold High School Family & Consumer Science Department.
Yiannis Gavalas – Southold School Athletic Association.
Catherine Glasser – Richard M. Osmer Memorial Sports Fund Awards.
Allison Heidtmann – Justin R. Flynn Memorial Scholar Athlete Award; Cindy Goldsmith Agosta Memorial Fund Award; Southold Faculty Association Scholarship; North Fork Chamber of Commerce Award; Mattituck Lions Club Scholarship; Southold Town Police Benevolent Association (PBA) Scholarship.
Matthew McGunnigle – Southold Music Boosters Scholarship; Office of the State Comptroller, Thomas P. DiNapoli Student Achievement Award.
Rylee Owens – Andreas Emmanuel Makakis Memorial Scholarship.
Antonio Piraino III – Louis Mancuso Sr. Scholarship Fund; Rotary Club of Southold, Vocational Excellence Award; Southold School Athletic Association; East End Lions Club Award; Dylan Newman Forever 5 Foundation Scholarship.
Alisa Rivera – George Markakis Memorial Scholarship.
Laila Rose – Suffolk County Chapter of the New York State School Facilities Association Inc.
Francesca Santacroce – William J. McGonegal Memorial Award; Office of the New York State Attorney General, Civic Ambassador Award; Southold Town Police Benevolent Association (PBA) Scholarship.
Travis Sepenoski – Stevan Fickeissen Memorial Award; Cindy Goldsmith Agosta Memorial Fund Award; North Fork United Soccer Scholarship in Memory of Morgan West; Southold PTA Student Award; Cross Sound Ferry Scholarship; Southold School Athletic Association; Dylan Newman Forever 5 Foundation Scholarship.
Jaden Smith – Schoolhouse Connection Scholarship; Southold Music Boosters Scholarship; Suffolk County Executive, Edward P. Romaine – Public Service Award; American Legion Griswold Terry Glover Post No. 803 Scholarship; Rotary Club of Southold, Barbara Bogel Ackermann “Most Improved Student” Scholarship; New York State Council of Administrators of Music Educators (NYSCAME) Scholarship; St. Peter’s Lutheran Church Scholarship; East End Counselors Association Award; National Conference of State Legislatures; Southold High School Family & Consumer Science Department.
Nathan Steinfeld – Salutatorian Award; New York State Academic Excellence Awards, Rank 2; Cindy Goldsmith Agosta Memorial Fund Award; Helen S. Wurth Memorial Scholarship Fund – Excellence in Foreign Language; Southold School Athletic Association; National School Development Council (NSDC) Award for Academic Growth & Student Leadership in Learning.
Anna Szymczak – Southold Fire Department Scholarship; Southold Faculty Association Scholarship; Southold High School Family & Consumer Science Department.
Lindsay Zaffino – Southold Fire Department – Keith Purcell Memorial Scholarship; Andrew McMorris Foundation Scholarship; Stony Brook Eastern Long Island Hospital; Southold PTA Student Award; Office of the New York State Attorney General, Letitia James – Triple “C” Award; Mattituck Lions Club Scholarship Thomas Cutinella Memorial Foundation Scholarship.
Olivia Zehil – Julia Helen Leonard Memorial Scholarship; Southold PTA Student Award; Southold School Athletic Association; North Fork Breast Health Coalition; Dylan Newman Forever 5 Foundation Scholarship; Mattituck Lions Club Scholarship.
Future Plans for Southold Graduates
Becker Agustin Perez –Workforce; Jaely Barraza Ruiz – SUNY/Buffalo; Connie Benson – University of Valley Forge; Emma Binkis – St. John’s University; Grant Bossen – Hofstra University; Shaun Bumble Jr. – Workforce; Robert Campos Velasquez – Workforce; Corinna Carbajal – Pace University; Marangely Carreto Gutierrez – Suffolk County Community College; Gabriella Ceballos –Pforzheimer Honors College at Pace University; Anna Colosi – Enlisting in United States Army;
Collin Cornell – University of Kentucky; Mauricio Cuellar – Workforce; Evan Czartosieski – Syracuse University; Lila Dailey – University of Kentucky; Alexa Diaz – Workforce; Brendan Domaleski – SCCC; Elizabeth Estrada – Stanford University; Caroline Fannon – SCCC; Angel Garza – SCCC; Yiannis Gavalas – SCCC; Catherine Glasser – Manhattan University; Allison Heidtmann – St. Leo University; Marlis Huas Orrego – Workforce; Cesar Huertas Boch – Workforce; Alan Huertas Rodríguez – SCCC; Natasha Kolsin – Alfred State College; Colin Kruk – Workforce;
Heidi Lopez – Continuing studies at Southold Junior Senior High School; Samantha Maskiell – East Carolina University; Matthew McGunnigle – University of Tennessee; Joel Mejia Gonzalez – Workforce; Jason Negron Rodriguez – University at Buffalo/SUNY; Rylee Owens – SUNY/Cortland; Christopher Palencia Castellanos – SCCC; Tyler Penny – Pace University, The Seidenberg School of Computer Science & Information Systems; Antonio Piraino III – Lynn University;
Noah Riddell – St. Joseph’s University; Alisa Rivera – BOCES Adult Education; Mychelle Rodriguez Alvarado – SCCC; Laila Rose – University of Pittsburgh; Kenedy Salazar Perez – Workforce; Francesca Santacroce – Ave Maria University; Travis Sepenoski – University at Buffalo/SUNY; Jaden Smith – Stony Brook University; Juan Sosa – SCCC; Nathan Steinfeld – Vanderbilt University; Anna Szymczak – University of Vermont; Joshua Uguna – Enlisting in United States Marine Corps; Lindsay Zaffino – Providence College; Olivia Zehil – Saint Anselm College.
