Class of 1975

In Reggie’s junior year, he started at offensive tackle and defensive tackle.  The football team  was CVC champions in football.  In his  Senior year he again started at offensive tackle and defensive end, and was moved back to defensive tackle based on injuries. Reggie made First team CVC offensive tackle, and First Team All State Suburban and Honorable Mention All State New Haven Register. He also participated in track on a CVC track team.  In Track he broke the WHS discus record three times and was seated 4th in the class LL state finals and finished 4th.  

After leaving Windsor High School, Reggie went on to Butler County Junior College in El Dorado, Kansas where he started as a freshman on the offensive line, and in his second year at Butler County, he earned first team, all conference and honorable mention all American. Reggie went on to earn a full scholarship to Murray State University where he started as a junior and as a senior. The team won the Ohio Valley Conference championship, first time in 25 years, and Reggie was honored as the lone senior and game captain. They were ranked number 2 nationally in college 1-AA, and played in the national semifinals.   Reggie then became a Graduate Assistant Coach where he coached the Offensive Linemen and scout team. At the end of the season he returned to Windsor and started his career. After 13 years with no football Reggie became an assistant coach at nearby Bloomfield High school. At Bloomfield,  he was lucky enough to be on 3 State Championship teams that produced numerous All State Players and college players who went on to play and graduate college. Nine players went on to play professionally, most notably Dwight Freeney. Reggie’s working career ended in 2014 after 20 years with the State Of Connecticut Department of Corrections. Reggie is the proud father of two children Rebekah and Reggie Jr., and my lovely wife Angela of 27 years. 

Class of 1977

Willie was the Male Athlete of the year Class of 1977.  He received 8 Varsity Letters in Football, Basketball & Track and was a proud recipient of the Distinguished Windsor Cup.  Willie was a 3-time Captain in  Football, Basketball & Track.  While Willie excelled in all sports, he was a 2 time All CVC selection in Football and also an All State Honorable Mention in Football.

Class of 1978

Dawn got her start playing athletics due to her cousins (Brian and Scott) seeking her and her sisters (Debbie and Doreen) to come outside and play.  Every afternoon and all summer long, they would  be playing softball and basketball.   When she started rec ball, girls were playing 6 on 6 separating offense and defense.  When she started playing on a travel team,  the new rules started.  Once she reached high school, 5 on 5 play was still fairly new.  

Junior year Dawn transferred to Windsor High from Milford High where she was a standout athlete .  She earned her varsity letters in each of the 3 sports she played with MHS and lettered as a freshman in basketball . She was recognized in her sophomore year as MVP for basketball.    

After moving to Windsor,  Dawn continued her athletic excellence as a varsity player in those three same sports. Both junior and senior year she earned All CVC honors for volleyball and basketball.  The CVC honor for volleyball senior year was especially nice, because her sister Doreen was recognized as well.  Dawn was awarded the Windsor Cup at the end of her senior year and she was also named Female Athlete of the Year, an award given to the outstanding female senior athlete each year. 

She was a volunteer coach for Windsor Little League Girls Softball and Windsor Rec boys basketball where she also was a referee.  She was awarded a 4 year scholarship from Fred Weisher  for her major in Recreation.

Dawn went to Southern Connecticut State College to earn a Bachelor’s degree in Recreation where she competed in club volleyball and travel softball. She was selected to be part of Southern’s softball team as a catcher, but after a heartfelt thought process, she declined.     Fun fact - while participating in Southern softball clinics she caught for Joan Joyce and actually was able to hit the ball.  

After graduation she got a job  as a Recreation Therapist working with individuals with developmental disabilities. She was extremely involved in the Special Olympics and very proud to be a coach for Team USA in the 1995 World Games in New Haven, CT.  All the while she continued to play in competitive sports leagues in basketball, softball and coed volleyball.

Dawn switched careers and became the Bethany Parks and Recreation director.  She was instrumental in starting feeder programs for high school athletics.   She was able to begin coaching youth softball, youth basketball and a few years of middle school basketball and softball.  

Dawn has daughters Courtney, Chloe and a son Chase.  All played in  high school athletics and college, where each were awarded their own accolades.    Now they turned to coaching both high school and travel clubs. Dawn has been having fun teaching her granddaughter Kaelyn  and looking forward to doing the same with future grand babies.

Dawn is honored to be a pioneer for women’s participation in competitive sports.  She is extremely grateful to her family , friends and teammates throughout her journey.  Her favorite comment from her coaches was “I just wish we had one more year.”  She wishes she had one more year too! 

Class of 1989 

Shawn was an outstanding athlete at WHS.  Shawn was awarded All-Conference and All-State in Football and he holds school records for total all-purpose yards and rushing yards. He is very proud of this time in Windsor.

Shawn was recruited by Arizona State after high school but they wanted him to play one year at Phoenix Community College to improve his academics. He left Arizona after a year. Reflecting back, he realizes he was a lost 19-year-old kid with no direction and homesick. He then played two years of semi-pro with the New England Crusaders. Many times people would come up to Shawn and ask “Aren’t you supposed to be in the NFL?”  That's why he is so  happy to see a host of players from Windsor who made it to the NFL so all the younger kids can see and say, “If they can do it, so can I." Shawn never saw anyone in Windsor who made it before him and he felt it was impossible. He feels we need more mentors out there to tell these kids they can go to college and make something out of themselves.

Class of 1989    

Connie graduated from Windsor High School in 1989. She was a starter and lettered in both soccer and softball all four years.  She was the lead-off batter in softball, with a career batting average over .400. She led Windsor in steals with an average of 30 thefts a year. Connie was chosen co-captain her senior year.  

In soccer she was Windsor’s center striker, scoring 55 career goals despite being sidelined with an ankle injury most of her sophomore year.  She was co-captain of the Warriors in her junior and senior year.  

Connie received multiple All-Conference and All-State awards.

• 3 time All-Conference in Softball

• 2 time All-State in Softball and Soccer

• 2 time All-Conference in Soccer

• Hartford Courant Athlete of the month in 1989

• Played in both soccer and softball State All-Star games

After WHS, Connie went on to become a two sport athlete at Mitchell College where she led the soccer team to an undefeated 17-0 season in 1989, and had 60 career goals in two years.  She captained the Pequot’s soccer team as a freshman and in her first year was the number 3 leading scorer in the Nation and in her second year she moved into the number 1 spot.

Connie received multiple awards:

• 2 time All New England in Soccer

• 1 year All-New England in Softball

• Mitchell College soccer MVP award in 1990

• Inducted into the Mitchell College Hall of Fame in 2001

Connie returned to WHS for 2 years as a JV and freshman soccer and softball coach, and was part of the coaching staff for the 1991 girls soccer State Champions.

Connie currently lives in Newington, CT. with her husband of 23 years and their dog Divot.  She loves cooking, music, and playing golf.

Class of 2010  

Leigh-Ann Jaggon graduated from Windsor High School in 2010. Leigh-Ann was a 2 sport athlete in soccer and lacrosse. In soccer, Leigh-Ann was the starting varsity goalie for 3 years. Unfortunately, she suffered an ACL tear her sophomore year during a lacrosse game. Despite her injury, she was named to the all-conference team and all-state team multiple years. She was named captain her senior year and played for the U-20 Jamaican National soccer team for one season.

Leigh-Ann went on to accept a full academic scholarship to the University of Connecticut. Despite missing an opportunity to be recruited due to her year long rehab, she was able to walk on to the UConn Varsity team. Leigh-Ann played from 2010-2013 and started her junior year. 

Upon graduating from college, Leigh-Ann pursued her doctorate in physical therapy and became a licensed physical therapist. While in graduate school, she also became a certified personal trainer in which she serves Windsor and the surrounding communities. She is currently on track to become a certified nutritionist while she works as a physical therapist and personal trainer.

Class of 2010 

Aaron graduated from Windsor High School in 2010. Aaron ran Cross Country and Track and Field for four years as well as 3 seasons of Indoor Track.  One season of swimming was enough to convince him to keep running.
Aaron served as WHS Cross Country Captain for 2 years. Head Coach Chris Rau coached Aaron to two CCC All Conference Titles in Cross Country.
Aaron attended the University of Vermont where he ran his first seasons of Cross Country and Track as a walk-on, earning an athletic scholarship after making the America East All-Conference Team in Cross Country his sophomore year. Aaron earned All New England Honors, All Conference Honors, and All IC4A honors and UVM Track MVP his senior year. He was coached to 1 conference, one UVM, and two facility records his senior track season in 2014 in the 5000m and 10000m races by Matt Bellfield and Joe Gingras. 

Aaron served as Cross Country team captain for 3 years and Track and Field his senior year. He received UVM’s MVP award for Track and Cross Country for 3 seasons. 

After graduating college, Aaron has lived in Vermont and Arizona. In the footsteps of his cousin the late Bill Lesinski (Inducted in 2015) Aaron is an avid outdoorsman. Aaron and his partner Bonnie call Fort Worth, Texas home. 

Class of 2011

Devin graduated from Windsor High School in 2011, where he was a starter on the Varsity Baseball team for 4 years. He was an All-Conference Selection for two seasons and an All-State Selection, First Team All Courant selection, and First Team All New Haven Register selection his Senior Year. As a captain of the baseball team his Senior Year, he batted .439 with 4 home runs, 16 RBIs, and only 4 strikeouts all season. On the mound, he had 4 wins with a 1.36 ERA and 78 strikeouts in only 61 innings.

Devin graduated as the number 225 player in the nation on Perfect Game and the number 1 player in the state of CT. He was a member of the prestigious Area Code and East Coast Professional teams, selected by professional scouts from the 30 Major League Baseball Teams, representing the top players from the Northeast Area. In addition to baseball, Devin played soccer and ran cross country during his time at WHS.

After graduation, Devin continued his baseball career earning a scholarship to the University of Connecticut, where he pitched from 2012-2016. There he was awarded the Hirschhorn Foundation Award, which was presented to the player who achieved exceptional mental toughness, overcame numerous setbacks, and transformed adversity into opportunity after returning from shoulder surgery. Devin led the Huskies in ERA in 2014 with a 2.05 ERA and left the program 9th all-time in games pitched with 65. After his time at UConn, Devin played for a year in the Frontier League for the Traverse City Beach Bums.

Devin now lives in Chicago, Illinois, with his girlfriend Anna, where he has forged a successful career in the medical device industry. He still enjoys watching baseball and goes to as many Cubs and White Sox games as he can.

Mike is the son of Jack O’Brien a former All American basketball player at Columbia Univ. and is a member of their Hall of Fame. Mike’s grandfather was inducted in the Basketball Hall of Fame in Springfield, Mass in 1961.

Mike is honored to join them in a Hall of Fame as a member of the WHS Athletic HOF.

Mike participated in sports at Windsor High School and was a letterman 4 times. He graduated from Windsor HS 65 years ago in 1958. Two years later, Mike enlisted in the US Air Force. He worked in the Electronics field and 2 years were spent working at Atlas F Missile silo areas in Nebraska. After his discharge, Mike and his family moved to Springfield, Mass for work reasons. Mike and his

wife Gayle (McGurk) and their 3 children Mike, Chris and Kathy all got involved in kid sports while there.

In 1976 Mike was recruited back into the Air Force on a test program utilizing prior enlisted service members. Again, Mike and his family were involved in youth

sports at various bases. At the end of this test program Mike was offered a position as a recruiter for the Air Force. He eventually became a Master Sgt. and became

the Senior Recruiter in Biloxi, Mississippi.

In 1982 Mike was discharged from the Air Force and returned to Windsor where he and his family became involved in the Windsor Diamond Club with coach Barry

Chasen and his staff. Mike eventually became President and Gayle became Treasurer for many years. This organization developed into the association that we are a part of now. Mike was also involved in the WHS Football Booster Club and was its President.

He was involved in fundraising for many clubs including the WHS Hockey Club. He stayed active in youth sports as a coach, umpire and referee for many years. Also, for years Mike could be found on the WHS campus or in the gym attending and supporting both boys and girls athletic events.

During his time working with the Diamond Club, Mike organized many fundraising trips to UConn games at Madison Square Garden. Additionally, Mike was one of the parents who accompanied the baseball team on a trip to California where they had a private visit and chat with Tommy LaSorda, LA Dodger manager and Ben Hines, his batting coach.

Additionally, they visited DisneyLand, Knotts Berry Farms, Anaheim Stadium, Universal Studios, Griffith Observatory and the highlight of the trip, listening to Coach Barry Chasen sing in the Hollywood Bowl. Although Mike now lives in the Tampa area of Florida, his heart still resides in Windsor.

Barbara was a woman ahead of her time.  She was a Physical Education Teacher at Windsor High for nineteen years from 1956 - 1974.  Barbara also was the boys golf coach for three years and was one of the top amateur golfers in the area.    She was also the advisor of the Girls Athletic Association, at a time before there were sports for girls in high school.  Two yearbooks were dedicated to her (1968 and 1975) which is a testament to how the students admired her.  In 1975, the Student Council sponsored the first annual Charity dance and all proceeds went to the Leukemia Society in honor of Miss Barbara Gough.

The Windsor High School 2009 Boys Basketball Team was crowned Class LL State Champions after defeating Crosby of Waterbury 72 – 69 at the Mohegan Sun Arena.  The Warriors finished the season with a 26-1 record and were voted the unanimous choice as the #1 team in the state in the New Haven Register Top 10 Poll. The 2009 State Championship was the 3rd in Windsor boys basketball in school history.

Numerous players from the 2009 team were offered Division 1 & 2 Full Basketball Scholarships, and others played Division 3 and Junior College Basketball.

Please welcome the 2009 Boys Basketball CT State Class LL Champions, to the Windsor High School Athletic Hall of Fame Class of 2023.