Founders’ Legacy: The Enduring Impact of Rosemary Armstrong and Sandy Weinberg.
From Leadership to Legacy: Celebrating Rosemary Armstrong—the Heart and Soul of Crossroads For Florida Kids
Please join us in celebrating Rosemary Armstrong and her extraordinary legacy of advocacy, leadership, and dedication to Hillsborough County’s most vulnerable children. A graduate of the University of Washington and Columbia Law School, Rosemary began her pro bono work in the 1980s with Bay Area Legal Services, representing low-income seniors, women, and juveniles, including survivors of domestic violence. Recognizing a critical gap in legal representation for children in foster care, she went on to co-found Crossroads For Florida Kids in 2012, creating a groundbreaking organization devoted entirely to advocating for vulnerable youth in our community.
After more than a decade as Executive Director, the organization’s only Board President, and the heart and soul of Crossroads, Rosemary has transitioned to the role of Founder/Director Emerita, where she will continue to advise and guide the organization she created: ensuring high-quality legal representation for children in need. Her decades of dedication, pro bono work, and mentorship have left a lasting impact on both children and the attorneys she has inspired.
As the architect of Crossroads, Rosemary built an “Army of Pro Bono Attorneys” in Hillsborough County. Under her leadership, over 280 volunteer attorneys were recruited and trained, contributing more than 55,000 pro bono hours to over 1,700 children referred by local judges. Leading by example, Rosemary has personally represented over 150 children in dependency, delinquency, and other juvenile cases, including youth with mental health challenges, intellectual disabilities, or survivors of human trafficking. She routinely visited clients at foster homes, detention centers, and other placements—developing close, trusting relationships and helping them achieve better life outcomes.
Rosemary’s extraordinary contributions have earned recognition locally, statewide, and nationally. Among her many honors are the Tobias Simon Pro Bono Service Award (2012), Tampa Bay Lightning Community Hero (2015), Girl Scouts Woman of Distinction (2017), ABA Livingston Hall Juvenile Justice Award (2018), HCBA Margaret D. Matthews Mentoring Award (2023), and the inaugural Florida Bar YLD Spirit of Excellence Award (2024). Most recently, Rosemary was named a Funding Florida Legal Aid (FFLA) Fellow and Legal Services Champion in 2025. Under her leadership, countless volunteers with Crossroads were also recognized with various awards for their pro bono service and Crossroads was the recipient of the Thirteenth Judicial Circuit Outstanding Pro Bono Service by an Organization in 2014 and 2021, respectively. As Founder/Director Emerita, she will continue to guide strategy, mentor future leaders, and ensure Crossroads thrives. Her vision and tireless advocacy have transformed child welfare advocacy in Florida, and we are deeply grateful for her lasting legacy of empowering attorneys and protecting vulnerable children.
Honoring Sandy Weinberg: A Distinguished Career of Legal Excellence and Advocacy for Crossroads
Please also join us in celebrating Sandy Weinberg as he retired this year after a distinguished 50-year legal career, recognized nationally for his work in complex civil litigation and white-collar criminal defense. A graduate of Princeton University and Vanderbilt Law School, Sandy began his career in Atlanta as a litigation associate at Powell Goldstein, followed by six years as an Assistant United States Attorney in the Southern District of New York. In 1985, he moved to Tampa with Rosemary, where he built a nationally-recognized practice first as a shareholder at Carlton Fields and then as a Partner of Zuckerman Spaeder LLP’s Tampa office, which he founded in 1991.
His expertise, integrity, and leadership earned him numerous honors, including recognition by the American Bar Association Criminal Justice Section’s Charles R. English Award (2012), the Department of Justice Director’s Award for Superior Performance, the Hillsborough County Bar Association “In the Trenches” Award (2009), the Bet-the-Company Lawyer of the Year Award (2015), as chair of the Criminal Justice Section of the ABA (2017) and as recipient of the Daily Business Review Lifetime Achievement Award (2021).
In addition to his professional accomplishments, Sandy has always been deeply committed to pro bono service. From his early days helping to establish Vanderbilt’s student legal services program to decades of advocacy for the wrongfully convicted and underserved, he has consistently exemplified the principle that lawyers have a duty to give back. That commitment was further realized in 2012 when Sandy co-founded Crossroads For Florida Kids with his wife, Rosemary Armstrong, and Tampa attorney Allison Singer, an organization dedicated to recruiting, training and mentoring volunteer attorneys to serve disadvantaged youth.
While Rosemary was the heart and soul of Crossroads, Sandy played a vital role in preparing the organization for long-term success. As Treasurer and Chair of the Fundraising Committee, he cultivated a broad and dedicated network of supporters, strengthening the organization’s foundation and positioning Crossroads to continue thriving well beyond his and Rosemary’s retirement. Beyond his leadership, Sandy personally represented disadvantaged youth in complex dependency and delinquency cases, dedicating hundreds of hours to give them a voice in the legal system. This commitment was recognized with the Thirteenth Judicial Circuit Outstanding Pro Bono Service by a Lawyer Award (2025). Sandy’s enduring legacy combines professional excellence with selfless service, leaving a profound impact on both the legal community and the lives of vulnerable children in our community. As Founder/Director Emeritus, he will continue to guide strategy and ensure Crossroads remains a resource for disadvantaged kids in Hillsborough County.
