Last month, Partners Ira Leesfield and Justin B. Shapiro attended the Key West High School’s Class Night alongside the Butler family to award senior James Osborne with the Dexter Butler College Scholarship.
This is the second, consecutive year that the firm has recognized an athlete and scholar from Key West High School.
“We are incredibly grateful for the opportunity to once again award this scholarship to a deserving student,” said Mr. Leesfield, Founder and Managing Partner of Leesfield & Partners and Chairman of The Leesfield Family Foundation.
Mr. Leesfield presents the 2026 Dexter Butler College Scholarship to Key West High School Senior James Osborne as he embraces Anita Butler, Dexter’s mother
The scholarship was created with the aim of preserving the legacy of community, kindness, and mentorship exemplified by Mr. Butler throughout his life. Last year, Dylan Martinez, now a rising sophomore at the University of Central Florida, received the award.
For him, the award’s significance was far more than financial.
“It reflects what Coach Dex stood for: resilience, kindness, and lifting people up when they need it most,” Dylan said. “It has helped me start college with confidence and the motivation to carry forward the same sense of service and perseverance that Coach Dex inspired in so many of us.”
He ‘Left a Legacy’
Presenting the award to James, Mr. Leesfield expressed the immense gratitude he has for the Butler family, who “adopted” him in as one of their own when he opened an office in the area in the 1980s.
Coach Dex, as he was affectionately known by his many students, left a legacy, Mr. Leesfield said, “with every student he touched and every person in his life.”
“Here’s the story: Key West is special,” he continued. “Driving down today, it had to be my three-hundredth trip … I realized why I keep coming back and why we are so honored and privileged to give this scholarship every year.”
Partners Ira Leesfield and Justin B. Shapiro stood with the Butler family and James Osborne, the 2026 recipient of the Dexter Butler College Scholarship, at the Key West High School’s 2026 Class Night.
James, who will go off to college in North Carolina in the fall, wrote in his application about the painful loss of his mentor and how, in his grief, he chose to put the lessons instilled in him by Mr. Butler into action.
“He saw something in me long before I ever saw it in myself,” James wrote. “He pushed me, protected me, challenged me, and—most importantly—he believed in me with a sincerity that changed my life.”
For more information about the Dexter Butler College Scholarship, visit: https://leesfieldfamilyfoundation.org/scholarships/#1574111729731-1ce4e253-b357
