Mike Boswell
Head Coach
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Mike Boswell joined the Bolles baseball staff in 2002 as an assistant coach and played a key role in the Bulldogs' state championship that season. He became head coach in 2004, served as an assistant coach in 2009 and 2010, then resumed the role of head coach in 2011.

Boswell notched his 400th career victory during the 2018 season, guiding the Bulldogs to the state semifinals for the third straight year. He led the Bulldogs to back-to-back state titles in 2016 and 2017. He was named the 2017 Division II/Region 3 High School Coach of the Year by the American Baseball Coaches Association and Diamond Sports and the Class 5A Coach of the Year in the 2016 and 2017 Florida Dairy Farmers Sports Awards.

Leading Bolles to two state titles and three state final four berths as head coach, Boswell was also instrumental in an additional three state titles and three final fours as an assistant. Prior to Bolles, Boswell served as head coach of Englewood High School. He earned Florida Athletic Coaches Association Coach of the Year honors in 1999 after guiding the Rams to the Class 3A state championship.

Boswell is a graduate of the University of North Florida and was an infielder in the Chicago Cubs organization. His wife, Laura, is a science instructor and advisor on the Middle School Bartram Campus. They have three children: Bolles graduates Bo '11 and Cody '14 and current student Lauren '19.

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Bob Shepherd
Assistant Coach

Bob Shepherd joined the Bolles baseball staff in 2013 as an assistant coach. His primary responsibility is working with the pitchers and catchers.

Prior to Bolles, Shepherd served as head coach of Fletcher High School from 2011-13. He also coached for several years at the collegiate level, as an assistant coach at the University of North Florida, Jacksonville University and Purdue University. Shepherd served as Auxiliary Coach for the 2009 Team USA Collegiate National team, and was selected as Pitching Coach for the 2010 Team USA 18U National Team. He also works as a Special Assignment Scout for the New York Mets.

Shepherd is a graduate of the University of Texas-Pan American and the University of North Florida. He has two sons at Bolles: Will '19 and Grant '20.

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John Newman '86
Assistant Coach

John Newman '86, who played both baseball and football for Bolles, continues to demonstrate his commitment to the Bolles tradition. Since joining the School staff in 1993, he has worked with the middle school, junior varsity, and varsity baseball and football programs. As head coach, Newman led the 2002 Bolles baseball squad to a state title and served as an assistant coach on nine of the football team's state titles. Newman serves as the upper school Dean of Student Affairs.

Newman is a graduate of Vanderbilt University with a bachelor's degree in human and organizational development. He played running back and punt return specialist for the Commodores football squad. Newman also earned a master's degree in education and health promotions from Vanderbilt.

John and his wife Kathy '86, a Lower School Whitehurst Campus faculty member, have three children who have attended Bolles: graduates Taylor '11 and Shaye '13 and Bryce '16.

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Chris Skinner '80
Strength and Conditioning Coach

Chris Skinner is a 1980 graduate of Bolles, where he was a member of two state runner-up baseball squads. Skinner returned to assist the baseball squad in 2007 after serving as an assistant coach from 1999-2005.

Skinner graduated from Vanderbilt University, playing on the Commodores' baseball squad. He has three daughters: Bolles graduates Peyton '08, Ellie '11 and Virginia '13.

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Chris Blaquiere
Assistant Coach

Chris Blaquire joined the Bolles baseball staff in 2017 after 26 years as a baseball coach and Sport Psychology instructor at Florida State College at Jacksonville. Blaquiere served as the Blue Wave's head coach for 15 years and split time as infield, outfield and base running coordinator, as well as pitching coach and academic coordinator. He spent the prior 11 years as assistant coach, serving as recruiting coordinator, infield coordinator, conditioning coordinator and academic coordinator. Blaquiere retired from FSCJ in November of 2015.

Blaquire played for legendary coaches Howard May at Terry Parker High School and Tommy Thomas at Valdosta State University. He earned a B.S. in Psychology, B.B.A. in Marketing, and B.B.A. in Management from Valdosta State University, as well as an M.A. in Counseling Psychology from Rider University.

He and his wife of 29 years, Candace, have a daughter Kylie and son Cameron, a 2014 Bolles graduate.

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Jimmy Lyons
Assistant Coach

Jimmy Lyons joined the Bolles staff in 2016 as an upper school math teacher and middle school baseball coach. He joined the varsity staff in 2018. Lyons comes to Bolles from Ponte Vedra High School where he served as a math teacher and baseball coach as well.

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Palmer Knight '89
Assistant Coach

Trey Leonard '05
Head Coach

Trey Leonard, a 2005 Bolles graduate, rejoined the Bolles baseball staff in 2017 and the Lower School Whitehurst Campus faculty as a P.E. coach in 2015. He previously served as the Bulldogs' JV head coach in 2011 and 2012. Leonard also coached the St. Augustine High School varsity squad in 2013 and 2014.

Leonard coached at the collegiate level for two seasons at the University of North Florida, where he was also a player for the Ospreys.

Leonard and his wife, Lauren, have a daughter, Marely.

Matt Denmark
Assistant Coach
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Matt Denmark joined the Bolles staff in 1998, currently serving as the Middle School Bartram Campus athletic director and middle school baseball coach.

Prior to Bolles, Denmark was a head coach at Episcopal High School and Providence School in Jacksonville. A graduate of the University of North Florida, he was a letterman on the Ospreys’ baseball squad. Denmark’s wife, Allison, serves as Upper School Dean of Girls. Their son Caleb is a 2010 graduate of Bolles and their daughter Abby is a 2012 graduate of Bolles.

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Caleb Denmark '10
Assistant Coach

Caleb Denmark is a 2010 graduate of Bolles, where he helped the Bulldogs baseball team win back-to-back state titles in 2009 and 2010. He has served as a coach with various middle school teams on the Bartram Campus.