The 139th commencement class of Staples High School is now part of history.
With pomp, circumstance and inspiring words from principal Stafford Thomas, 412 students graduated this evening, in beautiful — if a bit windy — weather at Paul Lane Field.
Presiding over his 7th graduation ceremony, Thomas lauded the Class of 2026’s leadership and “willingness to try,” when a schoolwide cellphone ban went into effect this fall.
Seniors embraced the change, made connections with each other — and came together around the game of hacky sack.
Looking back years from now, Thomas said, class members will see how the dots of their lives — including those formed at Staples — will similarly connect.

Staples principal Stafford Thomas.
The graduates — and family members packing the bleachers, and sitting on the hill beyond the field — also heard from valedictorian Isabel Jo and salutatorian Uma Choudhury.

Valedictorian Isabel Jo.
Thomas singled out 4 graduates who will be entering the military: Jennifer Londono and Finn Martens (Navy), Rhodes Redd (Marines) and Alessio Ramirez (Army).

A sea of blue, ready to graduate.
Then it was time for the real show. The diplomas were awarded. Official photos were taken. Kaia Levine and Elijah Falkenstein led the ceremonial turning of the tassel.
And just like that — 13 years after they entered kindergarten — the Staples High School Class of 2026 is ready to take on the world.

Faculty members greet graduates, as class members march in …

… and the graduates keep coming.

Dignitaries included (front row, from left) Board of Education chair Lee Goldstein, superintendent of schools Thomas Scarice, and assistant principal for the senior class Christine Cincotta. Standing at far left is 1st Selectman Kevin Christie.

Gunnar Eklund was one of many seniors with a decorative cap.

The final task before receiving diplomas: keeping those caps on.

Wynston Browne makes history. He is the the first non-speaking autistic student who communicates by spelling to graduate from Staples with a fully credited diploma.

After receiving their diploma, each graduate had an official photo taken. Congratulations, Seamus Brannigan! (All photos/Dan Woog)
(Check back tomorrow, for more “06880” graduation photos.)

Love this so much! Thank you for always showing up and supporting the children of Westport. You’ve been such a wonderful mentor to these kids!
Congratulations to you all! Many of you I’ve known since kindergarten and especially more recently at either BMS or CMS! Onwards! I’m sure you’ll make the world a better place!
Congratulations Class of ’26. You may not realize it now, nor should you dwell on it, but you have won something of a lottery. For whatever reason your parents chose to make a home for you in Westport. No matter where your education began; elementary, middle, or high school you have benefitted from a time proven system.
As Dan regularly highlights here so many Staples grads go on to do great things. Once you go forth in the world and meet other people you will be astonished to discover that many of these individuals lack the knowledge, critical thinking skills, compassion, altruism, and drive to succeed that you possess.
This opening monologue by Nick Carraway from “The Great Gatsby” always stuck with me after graduating:
“In my younger and more vulnerable years, my father gave me some advice that I’ve been turning over in my mind ever since.
‘Whenever you feel like criticizing anyone,’ he told me, ‘just remember that all the people in this world haven’t had the advantages that you’ve had.’
Good luck.
Congrats from a member of THAT Sixties Class (1966) to the graduates of 2026. May you pass congrats forwards to members of the Staples High Class of — wait for it — 2086! If I made it, you can, too. Ya know, It’s a wonderful life you will have. Maybe make a movie about it some day.
Best & Cheers.