Stephen Gaynor School

Orange Cluster teacher Jackie Dobish has been at Gaynor since 2014, and for the last five years she’s been a Co-Lead teacher with Jackie Kolbert, forming “the Jackies” of Room 404! For the Winter 2026 Gazette, we sat down with Jackie to learn more about her experience at Gaynor, her love of Orange Cluster, and the way the Co-Lead model helps set students up for success. Swipe to learn more, or read the full interview here: https://www.stephengaynor.org/2026/06/05/five-questions-with-jackie-dobish/ 🐊🧡

On May 7 & 8, the Gaynor community was treated to "Shrecktacular" performances of Shrek the Musical Jr.! Our talented Green and Blue Cluster students put on a ogre-tastic show worth more than a few onions. We are so proud of them! 🐊🎭🧅

May 29 was Field Day, and what a day it was! The whole school went to the fields on Randall’s Island for a day of fun athletic activities. Students competed in relays, soccer, and kickball, caught rubber chickens and stacked buckets, and most importantly, had a blast! Thank you to our wonderful Athletics team for planning the day, our Facilities team for assisting with set up, and Ms. Keffler for coordinating all the buses! It was truly a team effort. 🐊⚽️☀️

The Green Cluster recently went on their annual overnight trip to Trail’s End! And get this— 2026 marks ten years that Gaynor has been visiting Trail's End Retreats. Our students have a blast every time, and we can’t wait to be back!

It’s Giving Day! Help us reach our goal of 100% by clicking the 🔗 in our bio. Every gift counts towards support the Annual Fund, no matter the size. Go Gators! 🐊

Join us tomorrow, May 22, for a day full of Gaynor pride as the community joins together to support the school’s Annual Fund! Our teachers are what create the magic of Gaynor and the joy in our students’ education, and your gift helps make that possible. If you’d like to make your gift now, hit the link in our bio!

Last week the Pink Cluster opened their very own Post Office! Students worked as greeters, clerks, monitors, processors, inspectors, sorters, and even delivered mail between the North and South Buildings. Students and staff alike came to the post office with their letters in hand, ready to send. The post office is part of Pink Cluster’s exploration of community helpers that work in teams known as “businesses,” and operate as valuable members of the community. Students handled their roles with care and efficiency—it was the quickest post office we’ve ever been to! 🐊📬

This Friday, May 22, is Gaynor’s Giving Day! Stay tuned over the next few days to hear from some of our parents about why they donate on Giving Day. Every gift to the Annual Fund helps support future generations of students, ensuring Gaynor can continue changing lives in years to come. Can’t wait? Make your gift now: https://giving.veracross.com/gaynor/onlinegivingform

Today Blue Cluster student Goldie M. stepped into the role of Head of School! From morning greetings to meetings with Division heads, visits to the Purple and Pink classrooms, and even hanging out with Dr. Gaynor’s dog Georgie, she experienced everything a Head of School does in a day!

The Gaynor community spent yesterday, May 14, in Albany for Dyslexia Advocacy Day, organized by Assemblymember Jo Anne Simon.

We met with legislators, toured the Assembly and Senate floors, and advocated for students with dyslexia and language-based learning differences. We were especially proud to have Green Cluster students Audrey, Adrian, Gianni, and Mia, along with Blue Cluster student Liora, representing Gaynor throughout the day.

We also loved seeing Gaynor alumna Stephanie Brown ’13 helping coordinate the event through her work with Assemblymember Simon.