Shaped by grit, mentorship, and a deep-rooted connection to his hometown, Rob Thompson—West Haven High School Class of 1985—found his direction through decades of experience in the ever-evolving worlds of sports and media. From the practice fields of Ken Strong Stadium to executive roles with the NFL and Disney, Rob’s journey reflects the power of perseverance, purpose, and staying true to your roots.
Looking back at his time at WHHS, Rob doesn’t hesitate when asked who left a lasting impact. “For those that go back a ways, the teacher and coach that had the biggest impact—not just on me but hundreds of us who played football at WHHS—was Bert Siclari,” he said. “He was the perfect guy, at the perfect time, in the 1970s–1990s to be the voice of reason for a group of young men who needed a kick in the pants.” Siclari’s mix of discipline and compassion helped shape not just athletes, but future leaders—something Rob has carried with him ever since.
Now, with over three decades of experience, Rob’s professional journey speaks for itself. “I’ve spent my professional life in sports and media—over 30 years now—as an executive with the NFL, Disney, and UNH,” he said. “These days, I’m the Executive Director and Co-Founder of Gridiron 1880 Media Network.” His path is a prime example of how combining passion with persistence can lead to a career that evolves as you do.
When asked what advice he’d give to current WHHS students, Rob offers a mindset rooted in personal growth. “Run towards something that will positively impact your life,” he said. “Don’t run away from a bad situation or from West Haven just because you think it’s better somewhere else—you’ll end up dragging the same problems with you.” It’s a reminder that real change doesn’t come from escape—it comes from intention and direction.
Reflecting on the college decision process, Rob offers a piece of advice many students could benefit from hearing. “Pick a college—don’t let the college pick you.” It’s a simple but powerful shift in perspective—putting the student in control, rather than waiting to be chosen.
As for finding your path, Rob encourages patience, exploration, and a willingness to learn through trial and error. “You’ll figure out what you don’t want to do long before you land on a career path you love,” he said. “Enjoy your twenties.” It’s advice grounded in experience—a gentle push to take the pressure off and allow your direction to take shape over time.
From the hallways of WHHS to the highest levels of sports and entertainment, Rob Thompson’s story is a reminder that success isn’t just about where you go—it’s about how you grow. His words reflect not only the lessons he’s learned but the legacy he continues to build, one grounded in gratitude, purpose, and always moving forward.