A former collegiate athlete, coach, and now licensed mental health professional, Gabby Bennett, LSW, MA offers a rare perspective on total athlete wellness and comprehensive care supporting athletes on and off the court.

Gabrielle (Gabby) Bennett, LSW, MA grew up on the south side of Chicago, Illinois and began her journey as a volleyball player in the seventh grade. She created Cross Court Connections as an Obama Scholar for during the 2024 – 2025 program year, with the intention of addressing gaps within the wider volleyball community and expanding the volleyball community’s reach to all neighborhoods in Chicago. She firmly believes that every player deserves a pathway to opportunity, and envisioned Cross Court Connections as a means to ensure players, parents, and coaches were privy to information that would be pivotal to their developmental goals. Many players and their support systems are not aware of the intricacies of navigating competitive sports, especially leading to the collegiate level, and this organization aims to help players, parents, coaches, and their various support systems in navigating this process and learning more about the college/university options available to them. 

Prior to her coaching years, she played high school, club, and college volleyball. She graduated from St. Ignatius College Prep in 2016, where she played volleyball and was awarded Most Valuable Player (MVP) her senior year in 2015. She then went on to graduate from Wesleyan University, in Middletown, CT where she studied Psychology, Classics, and Education Studies. She was a starter for the Cardinals as a Middle Blocker and earned Conference Player of the Week honors in 2016. That year, she helped lead her team to their first NESCAC (New England Small Conference Athletic Conference) Tournament appearance in over 25 years, in 2017, their first NESCAC Tournament win in program history and the team’s first NCAA Regional appearance in 2017, the team’s first Regional Championship win and NCAA DIII Elite 8 appearance in 2018, and in 2019 helped lead them to a Second Round NCAA Regional Tournament appearance. Throughout her career, she was a varsity starter and conference leader in both blocking and hitting percentage statistics.

She began her coaching career in 2020, where she developed her coaching voice under the amazing staff and leadership at Elite Volleyball Program, coaching lessons and clinics for players of all ages and skills. She gained experience coaching at the club level at Michio Chicago Volleyball Academy for five seasons, working with 13 Excel, 13 Select, 15 Excel, and 17 Select from 2020 – 2024. In 2022, she coached her first high school season as the Junior Varsity Coach at Oak Lawn Community High School, and in November of that year started as the First Assistant Coach for Women’s Volleyball at Illinois Institute of Technology (IIT) where she remained for two seasons.

She earned her Master’s Degree in Social Work, Social Policy, and Social Administration (MA – MSW Equivalent) from the University of Chicago in June 2025, and uses her clinical experience to inform how she educates and supports parents of athletes as well as the athletes themselves. She completed both of her clinical internships at LIFT, Chicago – a non-profit that utilizes a multigenerational model to change family outcomes by coaching parents, and this model has become an essential framework she utilizes to evoke change for student athletes. Her experience playing and coaching in the various stages of volleyball have given her a deep perspective on the volleyball ecosystem as a whole and a strong understanding of the key tenants to success and longevity within the sport for athletes at any stage. Gabby understands the importance that a strong foundation in skillset, mindset, and an informed support system has on the ultimate success for a player. Cross Court Connections bridges these core elements of her vision together to support individual and structural growth within the volleyball community.