Jennifer Cleek
Assistant Coach

Jennifer Cleek​​​ was a four-year starter at Francis Marion University playing under Wes Moore, who is now head coach at NC State. Jennifer is the Peach Belt Conference's all-time career scoring leader. Cleek holds the PBC marks for free throws made in a season and career and free throws attempted in a career. Between 1996 and 2000, she helped lead the Patriots to a 103-22 record, the 1998 Peach Belt Conference Tournament championship, the 1999 PBC regular-season title, and four trips to the NCAA Division II national tournament, including three trips to the Sweet 16 (1998, 1999, 2000) and one appearance in the Final Four (1998). She was selected as the PBC's Player of the Year in 1998 and 1999 and earned All-America recognition in 1999 and 2000.

Cleek, a native of Knoxville, Tennessee, returned home to earn her bachelor's degree in Spanish at the University of Tennessee at Knoxville in 2002. She coached freshman girls at her alma mater, Bearden High School, and one year as an assistant coach at Mars Hill College.

Cleek and her husband Brian have three boys. She is an active volunteer in the community acting as President of the PTO at PVPV Rawlings Elementary School, volunteer basketball coach at the Ponte Vedra YMCA, and a Board Member for Community Hospice and Palliative Care.

Sherri Anthony
Assistant Coach

Sherri Anthony joined the Bolles girls' basketball staff in 2024, reuniting with one of her former players in Kelly Stevenson.​​​ Anthony recently retired after 42 years as an educator at various schools in St. Johns County as well as 39 years as the Nease girls' basketball coach. Her numerous coaching accolades are highlighted by her 2021 induction into the National High School Athletic Coaches Association Hall of Fame. She also earned Teacher of Year honors in 2009, National Coach of the Year honors in 2019 and Florida Association of Basketball Coaches Court of Legends induction in 2022.

Anthony's career record at Nease is 701-372 with one state title, a state runner-up, three Final Fours, nine Elite Eights, 11 Sweet Sixteens and 10 district titles. She guided Stevenson and her teammates to the 1999 Class 5A state title, with Stevenson earning state tournament MVP, 5A All-State, USA Today All-USA Honorable Mention, Florida Times-Union Player-of-the-Year and Florida Sports Awards Amateur Women's Basketball Player of the Year honors.

Anthony graduated from Keystone Heights High School and Flagler College, playing basketball and softball at both schools. She still holds the Flagler record for career assists (368) and ranks 13th on the Saints' all-time scoring list (751).

Anthony coached at her college alma mater as well, serving as softball coach for seven seasons and women's basketball coach for two seasons. She was inducted in the Flagler College Hall of Fame in 2011, received the Flagler College Professional Achievement Award in 2023 and is recognized by Flagler as a Distinguished Alumna.

Sean O'Neill
JV Head Coach

Sean O’Neill joined the Bolles faculty as an upper school history teacher and middle school girls' basketball coach in 2022. O'Neill led the middle school Bulldogs to undefeated seasons in 2022-23 and 2023-24, winning back-to-back IMSC championships. He joined the upper school girls' basketball staff as the junior varsity head coach for the 2024-25 season.

Previously, O’Neill spent five years as a middle school and AAU head coach in North Carolina, along with 15 years of coaching overseas in various international schools as an assistant and head coach of varsity girls’ programs.