Jack McFarland was born in Stamford, Connecticut, and grew up in Fairfield, where he attended Andrew Warde High School and was a three-sport athlete.
After graduating, he attended Southern Connecticut State University, where he played baseball. Following college, Jack was hired by Westport Public Schools to teach at Staples High School.
He and his wife, Norma—an English teacher at Trumbull High School—live in Monroe, Connecticut, and have four daughters: Kelly, Kenzie, Megan, and Abby.
In 1988, Jack began his coaching career at Fairfield High School as an assistant football coach under Gus Lindine.
In 1994, he moved to Staples High School as an assistant coach under Marce Petroccio, helping the team win five FCIAC Championships and three State Championships.
In 2005, Jack became the head baseball coach at Staples, compiling an outstanding record of 323–156, a 70% winning percentage. His teams captured four FCIAC Championships, appeared in seven FCIAC Finals, and won seven divisional championships along with four regular-season titles in 2009, 2010, 2014, and 2019.
Among his many honors are the 2019 FCIAC Coach of the Year, 2019 Overall Coach of the Year, the 2011 Westport Coaching Award, and the 2017 Westport Sports Person of the Year from the Fairfield County Sports Commission.
Jack is the all-time winningest baseball coach in Staples history, and his 2019 team achieved a perfect 35–0 record, the most wins in a season. Three of his players were named Gatorade Player of the Year in 2017, 2019, and 2023.
Since 1997, Jack has also served as Assistant Dean at Staples High School and remains active in the sport as a member of the CIAC Baseball Committee and the FCIAC representative on the CHSCA Baseball Committee.
He is honored for his exceptional coaching career and dedicated service to Staples High School.