Whit Mitchell 鈥�72, CEO & President of Working InSync and former renowned crew coach at Dartmouth, brought both humor and depth to the conversation. Reflecting on his time on the Hillside, Whit shared memorable and often funny stories that resonated with students while reinforcing a central theme: the importance of being a great teammate. Drawing from decades of experience advising CEOs and professional sports organizations, he emphasized that effective communication is not one-size-fits-all.

Through interactive exercises, Whit engaged students in exploring personality attributes, demonstrating how leaders must adapt their communication styles to bring out the best in individuals. His message was clear: understanding how others think and operate is essential to building strong, high-performing teams.

Michael Donaghey, Senior Director of Global Safety & Security at PayPal and former Deputy Chief Security Officer for the NBA, shared a compelling and deeply personal journey. From his days as a student-athlete at Brown University where he competed in both football and baseball to a career-altering injury that shifted his path, Michael spoke candidly about resilience, reinvention, and the importance of being a good teammate on the court and in life.

He went on to serve in the United States Secret Service, protecting two U.S. Presidents and traveling the world, before transitioning into leadership roles in professional sports and global security. Today, his work focuses on protecting people and organizations in an increasingly complex digital landscape.

Michael highlighted the growing sophistication of bad actors in the digital space and offered practical advice on how individuals can better protect themselves. His message underscored the importance of awareness, vigilance, and adaptability in a world where security challenges are constantly evolving.

Together, the panelists reinforced that the lessons learned through athletics teamwork, communication, perseverance, and leadership extend far beyond the field. Students left with a deeper understanding of how those skills can translate into meaningful and dynamic careers across industries.
The Pathways Series continues to provide South Kent students with unique access to alumni and industry leaders, offering real-world perspectives that inspire and inform their journeys beyond the Hillside.

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鈥淎lumni Weekend on the Hillside is always a special occasion. It’s an opportunity to renew old friendships, and to reminisce about experiences in the classrooms and on the playing fields. They say you can’t go home again, but Alumni Weekend is as close as it gets,鈥� Peter Thompson 鈥�67.

Thursday, June 5: Tee Off the Weekend
The festivities begin off campus with a friendly Golf Outing and Dinner at River Oaks Golf Club. It鈥檚 the perfect way to ease into the weekend鈥攃atching up with old friends, enjoying the scenic views, and celebrating the start of Alumni Weekend together.

Friday, June 6: Adventure, Stories, and Celebration on the Hillside
Friday kicks off with a tradition of camaraderie and adventure, as the leads a Hike to Bull Mountain, inviting all alumni to stretch their legs and take in the natural beauty that makes South Kent so special.

In the afternoon, head to Bringhurst Auditorium for Post Pigtail Perspectives to hear brief presentations on impactful experiences and insights.
Then, it’s game time! Grab a glove or cheer from the sidelines during a fun Alumni Softball Game.
As the sun sets, we鈥檒l gather for Cocktails in the Courtyard and then it鈥檚 time to head off to your class dinner at your favorite restaurant in town.

Saturday, June 7: A Day to Remember
Start your Saturday with a warm Welcome from the Head of School and hear inspiring updates from current South Kent faculty about the exciting work happening on campus today.

Next up is a fan favorite: the Annual “In My Day” Memories session in the Assembly Hall. Alumni of all generations come together to swap stories and honor the unique experiences that tie us all to South Kent.

Before lunch, don鈥檛 miss the much-anticipated Showcase and Signing of South Kent鈥檚 Centennial Book, “Enduring Foundations”, written by 鈥淔aculty Brat鈥� and beloved author Marge Smith. This commemorative moment celebrates the legacy of our school and the voices that built it.

After lunch and class photos, explore what鈥檚 new with a Tour of North Campus, led by Director Rich Chavka. Then, gear up for an exciting afternoon of athletics:

The Alumni Soccer Game (read more) on Farr Field, led by Coach Brennan and Alex Quinones 鈥�19 is expected have a big turn out and you can find more of your teammates on the .

The Alumni Hockey Game at South Kent鈥檚 indoor rink, led by Coach Belger along with Dillon Duncan 鈥�04 and Rich Brande 鈥�88

And Rowing on Hatch Pond, a serene and nostalgic way to close out the action.

Saturday evening begins with a meaningful Alumni Memorial Service in St. Michael鈥檚 Chapel, followed by the grand finale: the Alumni Dinner and Awards Ceremony, honoring outstanding members of our community and closing theweekend on a high note.

鈥淎lways a highlight of the year, Alumni Weekend delivers each time. The connections and reconnections that people make over the weekend are amazing and stay with you forever鈥� – Rich Brande 鈥�88.

Register Now
With the weekend quickly approaching you can preview classmates attending on the registration page. If you need a place to stay dorm lodging is available, as well as plenty of places in the town of Kent — and you can use our special SKS discounts found here. Please you鈥檇 like to join or attend, and make sure to to let us know if you鈥檇 like to participate in future Networking Events, Pathways Talks, Career Days, and more.

We can鈥檛 wait to welcome you home to the Hillside. See you at Alumni Weekend 2025!
Missed last year’s Alumni Weekend? Check out the Centennial Celebrations from 2024 and post .

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This year, Michael led the music for our Martin Luther King Day Eucharist, bringing his inspiring artistry to this meaningful occasion. The Hillside community joined together to honor Dr. King鈥檚 teachings, reflecting on the principles of justice, unity, and service that continue to shape our School鈥檚 values. A formal dinner followed the 5:30pm service, providing an opportunity for further fellowship and remembrance of Dr. King鈥檚 enduring legacy.

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