Our Training Staff
Adam Kolarek- Pitching/Hitting/fielding
Adam Kolarek brings elite professional experience, versatility, and championship-level knowledge to every athlete he works with. A former Major League relief pitcher with a 15-year professional career, Adam spent seven seasons at the MLB level, competing and succeeding at the highest level of the game.
Adam played collegiately at the University of Maryland, where he contributed both on the mound and at first base. His two-way collegiate background gives him a unique perspective when working with players, allowing him to coach pitching and hitting with a complete understanding of how both sides of the game connect.
During his Major League career, Adam pitched for the Tampa Bay Rays, Los Angeles Dodgers, Oakland Athletics, and New York Mets organizations. He was a key contributor to the Dodgers’ bullpen and a member of the 2020 World Series Championship team, trusted to perform in the most pressure-filled moments of the season.
As an instructor, Adam works with both pitchers and hitters, focusing on mechanical efficiency, approach, confidence, and game awareness. Whether refining a pitcher’s arsenal or helping hitters develop a consistent, powerful swing, Adam applies the same attention to detail and professional insight that carried him through a long and successful career.
Doug Caraway- Catching/Hitting/Fielding-Director of College Recruitment
Doug Caraway brings decades of high-level playing and coaching experience to every athlete he works with. A former collegiate and professional catcher, Doug played college baseball at Grand Rapids Community College and later at the University of Pittsburgh, where he served as a team captain and earned All–Big East honors.
From 2000–2003, Doug played professionally in independent baseball, gaining three years of pro experience along with multiple organizational tryouts. His playing career includes back-to-back NJCAA National Championships (1996, 1997), 1998 All-MCCAA Conference honors, and 2000 All–Big East recognition.
Following his playing career, Doug transitioned into coaching, working with numerous high school programs and collegiate summer teams. He currently coaches the 17U Rawlings Tigers in Westminster, Maryland.
Doug specializes in hitting, fielding, and catching instruction, with a strong emphasis on college recruiting and player evaluations. He has helped hundreds of athletes successfully move on to college baseball at every level by guiding families through development plans, exposure opportunities, and the recruiting process.
Doug’s mission is simple: develop fundamentally sound players, prepare them for the next level, and help them maximize both their ability and their opportunities in the game.
Mike Bordick — Hitting & Fielding Instructor (only available select dates)
Mike Bordick brings elite Major League experience, defensive excellence, and a lifelong passion for teaching the game to Rick Dempsey Sports. A native of Michigan who ultimately settled in Maine, Mike developed into one of the most reliable and respected shortstops of his generation.
Mike starred at Hampden Academy in Hampden, Maine, where his impact on the program was so significant that the school’s baseball field was later named in his honor. He went on to play collegiate baseball at the University of Maine, competing for the Black Bears and further establishing himself as a premier defensive infielder.
Signed as an amateur free agent by the Oakland Athletics in 1986, Mike made his Major League debut in 1990 and went on to enjoy a 14-year MLB career (1990–2003). He played for the Oakland Athletics, Baltimore Orioles, New York Mets, and Toronto Blue Jays, appearing in 1,720 Major League games.
Known league-wide for his defense, Mike set Major League records for most consecutive errorless games (110) and most consecutive errorless chances (543) by a shortstop. He finished his career with a .982 fielding percentage, was selected as an MLB All-Star in 2000, and was later inducted into the Orioles Hall of Fame in 2011.
Following his playing career, Mike spent 11 seasons as a broadcaster and analyst for MASN Orioles, giving him a unique ability to break down the game with clarity and precision. Today, he dedicates his time to instruction through lessons, camps, team practices, and speaking engagements, helping players improve not only their skills, but their understanding of the game.
As an instructor, Mike specializes in hitting and defensive development, with a strong emphasis on fundamentals, preparation, and mental approach. His goal is to help athletes of all ages build confidence, play the game the right way, and reach their full potential.
Rick Dempsey — Catching/Hitting/Fielding (only available select dates)
Rick Dempsey brings championship pedigree, elite catching expertise, and a lifelong commitment to the game to Rick Dempsey Sports. A former Major League catcher with a 24-year professional playing career, Rick is widely regarded as one of the toughest, most durable, and most respected catchers of his era.
Rick began his Major League career with the Minnesota Twins in 1969 and later played for the New York Yankees before being traded to the Baltimore Orioles in 1976. He became the Orioles’ starting catcher from 1977 through 1986, catching a club-record 1,222 games behind the plate. Rick finished his playing career with stops in Cleveland, Los Angeles, and Milwaukee before returning to Baltimore for his final Major League season in 1992.
Over his career, Rick caught 1,633 Major League games, ranking 21st all-time, and finished with a .988 career fielding percentage. He appeared in three World Series—1979 and 1983 with the Orioles and 1988 with the Dodgers—winning two World Series championships. Rick was named World Series MVP in 1983, a rare honor for a catcher, and famously caught the final out of the 1988 World Series.
Following his playing career, Rick transitioned into coaching and broadcasting. He spent five seasons managing in the Minor Leagues and served as a Major League coach with the Los Angeles Dodgers. From 2002–2006, Rick returned to Baltimore as a Major League coach for the Orioles, working as a first base coach, third base coach, catching coach, and bullpen coach. He also spent many years as a pre-game and post-game analyst for the Orioles on MASN, becoming one of the most trusted voices in Baltimore baseball through the 2020 season.
Beyond the field, Rick has been a staple of the Baltimore community since the mid-1970s, participating in thousands of charity events, baseball clinics, golf outings, auctions, and speaking engagements. Through both his playing career and his continued contributions off the field, Rick has become one of the most beloved figures in Baltimore sports.
As the founder of Rick Dempsey Sports, Rick remains deeply committed to teaching the game the right way—through fundamentals, preparation, mental toughness, and a genuine love for baseball. His Columbia, Maryland training facility offers private lessons, camps, coaching clinics, and team instruction, continuing a lifelong mission of developing players and giving back to the game.
Calvin Maduro — Pitching Instructor
Calvin Maduro brings Major League experience, international playing success, and extensive professional coaching knowledge to Rick Dempsey Sports. A native of Aruba, Calvin played five seasons at the Major League level between 1996 and 2002 and has spent decades developing pitchers at the professional level.
Calvin pitched in the Major Leagues for the Philadelphia Phillies and the Baltimore Orioles, competing against elite hitters and gaining firsthand experience at the highest level of the game. In addition to his MLB career, he represented the Netherlands in international competition, including the 2004 Summer Olympics in Athens, where the Dutch National Team finished sixth. During that time, he also played professionally for the Dutch major league club HCAW.
Following his playing career, Calvin transitioned into coaching and player development. He served as pitching coach for the Aberdeen IronBirds, an Orioles affiliate, before continuing in player development roles with the Gulf Coast Orioles. In 2010, Calvin became a professional scout for the Baltimore Orioles, a role he held for over a decade, evaluating and developing talent across all levels of the game.
In 2021, Calvin returned to on-field instruction as the pitching coach for the Gulf Coast Twins, continuing his long-standing commitment to pitcher development.
As an instructor, Calvin specializes in pitching mechanics, arm care, and game preparation, drawing on his experience as a Major League pitcher, international competitor, coach, and scout. He is passionate about helping players understand not only how to pitch, but why—preparing them mentally and physically for success at the next level.
Jorge Maldonado — Hitting & Infield Instructor
Jorge Maldonado brings over 20 years of baseball knowledge and coaching experience to Rick Dempsey Sports, specializing in hitting development and infield instruction. His approach emphasizes sound fundamentals, attention to detail, and building confident, game-ready players.
Throughout his career, Jorge has played and worked alongside Major League players and coaches, including Leo Gomez of the Baltimore Orioles, Carlos Baerga of the Cleveland Indians, and Kevin Bradshaw with the Detroit Tigers organization in Lakeland, Florida. These experiences have helped shape his teaching philosophy and high standards for player development.
Jorge served as a hitting and infield coach at Archbishop Curley High School, where he helped guide the program to a State Championship in 2018. He currently coaches at Archbishop Spalding High School, and in 2022, helped lead Spalding to another State Championship.
With championships at two different programs, Jorge holds the unique distinction of being the only coach in MIAA baseball history to win state titles as a coach at two separate schools.
As an instructor, Jorge is passionate about developing hitters and infielders through consistent mechanics, strong preparation, and a clear understanding of the game. His goal is to help players maximize their ability while instilling the confidence needed to succeed at the next level.
Chris McNeal — Softball/Baseball Catching/Hitting/Fielding Instructor
Chris McNeal brings a well-rounded background in softball instruction, youth development, and sports performance technology to Rick Dempsey Sports. A Baltimore native, Chris combines on-field coaching experience with advanced training tools to help softball athletes build confidence, consistency, and game-ready skills.
Chris earned both his Bachelor’s and Master’s degrees in Sports Management from Towson University and Coastal Carolina University, giving him a strong foundation in athlete development, program leadership, and facility operations.
He currently serves as the Varsity Softball Head Coach at Maryvale Preparatory School and brings over six years of baseball and softball coaching experience at multiple levels. As a former catcher and a two-year varsity team captain at Pikesville High School, Chris understands the physical and mental demands of the game and applies that insight directly to his instruction.
Chris specializes in softball catching and hitting instruction, utilizing modern performance tools including Diamond Kinetics, HitTrax, and Blast Motion to provide measurable feedback and customized development plans. His coaching background also includes serving as a four-year volunteer coach with BUBA, former Program Director for i9 Sports Baltimore, and experience in sports management and marketing roles.
Chris is passionate about teaching the next generation of softball players, building confidence, and helping athletes reach their full potential both on and off the field.
John Fowler — Hitting, Infield & Pitching Instructor
John Fowler brings a strong blend of professional playing experience and player-focused instruction to Rick Dempsey Sports. John was drafted twice by the Baltimore Orioles organization (1986 and 1988) and spent three seasons in professional baseball, competing at the Rookie, Low-A, and High-A levels, including time with the Frederick Keys.
Before turning professional, John played two seasons at Frederick Community College, earning All–Maryland Junior College honors both years. He began his baseball career at Brunswick High School, where he was a three-time All-MVAL selection and was named Frederick County Player of the Year during his senior season.
As an instructor, John focuses on hitting development, infield fundamentals, and introductory pitching instruction. He emphasizes proper mechanics, game awareness, and building confidence, making him an excellent resource for players developing their skills and learning the foundations of the game.
John is passionate about helping athletes grow through sound fundamentals, detailed instruction, and lessons tailored to each player’s level and goals.
Daquan Wheeler – Strength & Conditioning | Speed & Agility
Daquan Wheeler is a dedicated strength and conditioning coach specializing in speed, agility, and athletic performance development. As part of Win Sports & Fitness, Daquan brings a high-energy, results-driven approach designed to help athletes and everyday individuals push past their limits and reach their full potential.
At Win Sports & Fitness, the mission is to inspire and empower through expert coaching, personalized programming, and a commitment to excellence. Daquan focuses on building explosive power, functional strength, and confidence—both on and off the field—while creating a training environment that promotes discipline, resilience, and character.
More than just a gym, Win Sports & Fitness is a family built on community and culture. Daquan takes pride in supporting every athlete who walks through the doors, helping them thrive physically, mentally, and competitively.
Who Daquan Works With:
- Athletes: Speed, agility, strength, and explosive power to dominate their sport
- Adults: Bootcamps, small group training, and 1-on-1 coaching for fat loss, strength, and confidence
- Teams: Custom strength and conditioning programs for schools, clubs, and organizations