Legacy Pro Sports

The Team

Legacy Pro Sports team is devoted to helping retired Professional Athletes manage their personal, financial, and medical matters. We acknowledge the difficulty former players face when they step away from professional sports. Our primary goal is to satisfy the unique needs of each athlete and to guarantee that they lead a fulfilling and quality life after the game.


Founder and President


Founder and Vice President

Brandon Siler

Brandon Siler is the Founder and President of Legacy Pro Sports and is originally from Daytona Beach, FL. He attended Evans High School before receiving a football scholarship from the University of Florida, where he majored in Criminology. Brandon earned SEC Freshman of the year in his first season with the Gators and was Captain for the 2006 National Championship Team, in which he earned second-team All-SEC and third-team All-American honors from the Associated Press.

 After being drafted by the San Diego Chargers, Brandon played instrumental roles at linebacker and on special teams for four seasons. From there, he would play an additional two seasons with the Kansas City Chiefs. Upon retirement from the NFL, Brandon worked in consulting with Cemex before transitioning to the next phase of his career. 

 While applying for NFL Disability Benefits himself, Brandon came to realize the difficulties and intricacies involved with the process and set out to do something about it. In founding Legacy Pro Sports, Brandon aimed to create a hand-in-glove business that listens to the issues former professional athletes face, and vigorously acts in their best interest.

 Today, Legacy Pro Sports represents over 5,000 former athletes. This year, they are on track to assist former players to win over $200 million worth of disability claims.

Ryan Sherry

Ryan Sherry is a Co-founder of Legacy Pro Sports and is originally from Fort Myers, FL. He attended Canterbury School and received an athletic scholarship at the University of Florida playing on the Men’s Tennis team as a 4-year letterman. He graduated from the Warrington College of Business Administration with an emphasis in Sports Management. Ryan played in two SEC team championships from 2003-2005, received MVP in 2005, and SEC Scholar-Athlete honor rolls from 2003-2005. He is a member of Sigma Phi Epsilon Fraternity Florida Chapter and Florida Blue Key: a student honor and service society at the University of Florida.

After graduating within a year’s time, Ryan positioned himself in the Pickleball Pro Division as a Top 7 Singles player in the World. He became an entrepreneur in the entertainment industry and after six years he sold several businesses and entered into the securities industry. As a member of the Art and Science of Successful Planning organization, he also worked for his family’s dental practices in the areas of business development and marketing.

Ryan’s current focus is assisting former professional athletes in filing claims for disability plans, supporting them throughout the process, and helping them maintain a quality of life as they transition from one chapter to the next.

Legacy Pro Sports represents over 5,000 former players. This year they are on track to assist athletes collectively to win over 200 million dollars worth of disability claims.

Krystyna Hammond


Razanna Thomas


Grace De Paz


Michele Blakey

Dir. of Orthopedic & Neurocognitive Benefits

Devante Walton

Dir. of Legal & Medical Records

Michele Richardson

Dir. of Communications & Public Relations

David Siler

Intake Specialist

Eric Slusser

Records Specialist

Maisha Scott

Recruiting Specialist

Dante Johnson

Recruiting Specialist

Adam Freedman

MLB Recruiting Consultant

Victoria De Paz

Administrative Coordinator

Sports & Health Blog

NFL Pension Benefits for Vested and Non-Vested Players

NFL Pension Benefits for Vested and Non-Vested Players

The National Football League (NFL) has been a powerful presence in American professional sports for decades. With its long-standing history and prestigious reputation, it's no wonder the league has some of the most generous pension benefits among professional sports...

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How It Works

Legacy Foundation

Case Studies

The Team