Colby Confer Shannon
Athlete
Class of 2001
Soccer & Lacrosse
Colby was born in New Haven and lived her first five years in Milford with Mom (Phyllis) and Dad (Phil) before moving to North Madison when she was around six years old. The family then settled on the south side of Madison when she was in fifth grade.
Colby began playing soccer and softball in the town’s youth programs with Dad as her coach. She also played basketball, tennis and did some horseback riding. Lacrosse was never on her radar early on and she didn’t really get started until around sixth grade. Dad and Colby would practice lacrosse in their yard all the time and Dad, himself, was a college football and lacrosse player at UNH.
When Colby reached high school, she played both soccer and lacrosse, becoming gradually more passionate about lacrosse. She had been mostly a defender in youth lacrosse, but with the help of high school coach Pat McCahill (MAHOF 2013), Colby received an opportunity as a freshman to get a varsity spot and soon a move to attack developed.
A few special moments in high school were scoring a goal against Guilford in her senior year and scoring the winning goal against Simsbury in the state tournament to help Hand get the furthest it had ever gone in states at that time in 2001.
Here are some High School accomplishments
• Started three years on varsity
• Captain her senior year
• Three-year All-SCC Conference
• Two-year All-State
• Senior year - Honorable Mention All-American, High scorer.
Colby received some interest to play in college. See attended a select lacrosse camp and received interest from UConn, BC, UMass and Stonehill. She loved Stonehill, their coach and the teammates she met, and Stonehill became the choice. She was a four-year Division II scholarship starter. As a freshman, Colby received Honorable Mention All NE-10 Conference. A special memory and moment was her "Golden Goal" scored with 11 seconds left in the NCAA D2 Championship game giving Stonehill its first National Title.
Here are some other College achievements:
• Three-time NE-10 All Conference
• Two-time NCAA All Tournament
• Two-Time All-American
• Captain in junior and senior years
• Senior year Division II NCAA National Championship high scorer
• 2017 Stonehill College Hall Of Fame Inductee
• Upon graduation, she was the all-time leading scorer (252 points). Only the second player to surpass 200 points.
Team Achievements:
• Senior year 21-0 record
• Two-time National Championships 2003, 2005.
After her college career ended, Colby attended Southern Connecticut State University for her master’s in education. While working on her master’s degree she had an opportunity to become an assistant coach with the Quinnipiac Women’s Lacrosse team, which she did for three years. Also, Colby found time to be a runner throughout these years running in many marathons.
Her life would change forever when living in New Haven and having dinner in a restaurant she met a young man who came over to her and said, "Weren’t you an All-American Lacrosse player?" The rest is history. Patrick Shannon, a graduate of Hand High School Class of 1999, married Colby Confer in 2009 at Longboat Key, Florida. Patrick is a Financial Advisor with Ameriprise. Patrick and Colby have been living in Madison for 13 years. They have three children, Carter (15), Keni (8) and Taden (5). So far, Keni is the Lacrosse player, while Carter plays basketball and Taden is just starting. Patrick is involved in coaching them and Colby is actively coaching in the Madison Youth Lacrosse program.
Madison is a town blessed with many former school athletes returning home to raise their families and begin the process of giving their children the Madison life-style and education that they received. Patrick and Colby have come full circle and are enjoying our community.
We congratulate Colby and welcome her into the Madison Athletic Hall of Fame!
Emily Jablonski
Emily Jablonski
Athlete
Class of 2010
Field Hockey & Lacrosse
Emily Jablonski established herself as one of the most accomplished
multi-sport athletes in Daniel Hand High School history, excelling in both field hockey and lacrosse. A dominant competitor, gifted leader, and exceptional teammate, she earned multiple All-State and All-Conference honors while setting a standard of excellence that few athletes have matched.
Over the course of her career, Emily was a four-time First Team All-State selection and a six-time First Team SCC All-Conference honoree. She was recognized three times as the New Haven Register All-Area MVP—twice in lacrosse and once in field hockey—reflecting her remarkable impact in both sports.
Her senior lacrosse season in 2010 ranks among the finest ever produced by a Connecticut high school lacrosse player. Emily led the entire state with 128 points, scoring 82 goals while adding 46 assists. She earned First Team All-State honors, All-American Honorable Mention recognition, and New Haven Register All-Area MVP while leading Daniel Hand to the SCC Championship.
Lacrosse Coach Kevin Siedlecki remembers Emily as much more than an exceptional scorer. "Emily was a high performer who was always looking out for her teammates, setting them up for success. She was a tremendous goal scorer. She could get her hands free and get a strong shot off in places most high school athletes couldn’t. She worked so hard to develop that ability, but more importantly, she was always team-first."
That unselfishness defined her game. During her senior season, Emily averaged nearly four goals and three assists per game, creating opportunities for teammates almost as often as she scored herself. Coach Siedlecki points to one statistic that says it all—Emily converted an astonishing 70 percent of her shots. Anything over 50 percent is considered outstanding. She wasn’t simply taking shots, she was making the right decisions, choosing her opportunities wisely, and trusting her teammates when they had the better look. As Coach Siedlecki simply put it, "When it came to Emily, she really was unstoppable."
Her success on the field hockey field was equally impressive. As team co-captain, Emily recorded 11 goals and eight assists while leading the Tigers to a perfect 10-0 SCC regular-season record, the conference championship, and a CIAC Class M semifinal appearance. Her outstanding play earned First Team All-State, First Team All-Conference, and New Haven Register All-Area MVP honors. Field Hockey Coach Sue Leckey (MAHOF 2021) described Emily perfectly: "Emily is dedicated, passionate, driven, intelligent and unbelievably positive. These qualities translated directly to the field—her ability to understand the game, lead the team, and rise to the occasion. In big moments, she always found a way to get the job done." Yet Emily’s legacy extends well beyond statistics and awards. She was known for her relentless work ethic, unselfish play, and unwavering commitment to her teammates. She possessed the rare ability to elevate the performance of everyone around her while consistently delivering when the stakes were highest.
Emily’s achievements extended beyond athletics as she was also recognized as a CIAC Scholar-Athlete, reflecting her commitment to excellence in the classroom as well as in competition.
Emily’s success continued at Williams College, where she competed in both field hockey and lacrosse in one of the nation’s premier Division III athletic conference, the NESCAC.
Today, Emily continues to make a meaningful impact through her work in philanthropy as the Bay Area Director of Major Gifts for the University of Michigan. She lives in Oakland, California, with her partner, Alex, and enjoys reading, ceramics, and hiking with their dog, Peanut.
Please join me in congratulating Emily Jablonski—a remarkable athlete, outstanding teammate, and a most deserving inductee into the Madison Athletic Hall of Fame!
Gregg Nappo
Gregg Nappo
Athlete
Class of 2006
Baseball
Decades ago, a little boy from Staten Island who loved Andy Pettit and Mariano Rivera, started exercising an arm that would take him to the top of the baseball world by skipping stones off a large pond near his home. He was also blessed by a family that supported him and a dad who always had time to grab a glove and play catch.
Arguably the best pitcher to play for Daniel Hand and, for that matter, the state of Connecticut began his career on the little league fields of Madison under the watchful eye of longtime little league icon Ben Scheraldi.
He began his career as a first baseman but soon it was apparent that the hill was where he belonged. In high school, he was challenged by his head coach Bryan Gywnn. "Coach Gwynn was a catalyst for greatness by implying that I was not good enough. I love it when people underestimate me." Whatever coach said, it worked.
By his junior year he was one of the best pitchers in the SCC. In the state playoffs Nappo let everyone know he was coming by pitching 5 and 2/3 innings of shutout baseball, while recording 13 strikeouts in Hand’s second round game only to watch it slip away in a last inning loss.
In his senior year he helped lead the team to a regular season SCC Championship and a state top 20 ranking before losing in the semi-finals of the tournament to Ledyard.
Gregg was largely overlooked by college coaches but had a burning desire to attend UCONN and play for legendary coach Jim Penders. Unfortunately, it was teammate Andrew Davis who got the letter asking if he was interested in UCONN. Once again, adversity was no match for his work ethic and resilience. (He would remind coach Penders many years later that he never got the letter.)
Gregg started attending showcases around the region. In his first showcase, he got to pitch an inning, striking out three consecutive batters. The coaches in attendance wanted to see him pitch from the stretch so they put a man on first which he immediately picked off. The eyes of the baseball world were now officially open to the upstart of Madison. Suddenly, local power houses like UNH were on the phone along with Holy Cross and many other programs… but not UCONN.
Later that summer, he attends the weeklong UCONN baseball camp. The night before camp he threw 110 pitches versus Branford in a legion game not knowing that on the next day he would be expected to pitch three innings against his fellow campers.
He was able to get through the three innings but his arm was not where it needed to be. He went to the pitching coach and told him the situation and asked for an extra day to recover. The day was granted and in that three-inning outing he struck out 8 and picked off the one man to reach base.
Finally, his dream was nearing reality. Behind the scenes coach Penders wanted to see more and came out to Orange to watch his next Legion outing. His legion coach at the time was current Hand head coach Travis LaPointe who "lit the fuse" that would ignite his career. In that outing he pitched 6 scoreless innings while striking out 11 batters and that night he agreed to become a Husky.
The Huskies were losing 300 innings worth of pitchers that year so although he had other offers, he decided to follow his dream hoping that he could make an early impact on the program.
His career at UCONN was punctuated by many special moments beginning with him throwing a complete game shutout as a freshman in the Big East Tournament getting them into the finals. He recalls striking long time big leaguer Todd Frazier out twice in a game against Rutgers.
In his senior year, he recalls a series against national powerhouse Clemson in the regionals where he won two games and was the unanimous MVP of the tournament. Later that evening Gregg Nappo became a major leaguer being drafted by the Marlins.
(Another future hall of famer George Springer, a teammate, joined Gregg’s draft celebration). He went to Greensboro NC where his catcher was JP Realmuto and they won the league championship in the A league.
In double A he became a 7/8 inning setup man and attended big league spring training in Jupiter Florida where he would be a regular participant for the next seven years. For the next three seasons he would compete in Triple A ball and chalk up impressive numbers as a reliever.
Gregg battled back injuries and culminated his career playing for the Columbian National team in the World Baseball Classic. He was eligible because his mother was a Columbian. He played with several big leaguers, they played against Team USA, and the Dominican Republic in front of 60,000 people.
He entered the seventh of the USA game and got the lefty out before leaving the game. He finished his career in New Britian. Gregg holds several UCONN records. He is first in innings pitched, second in strikeouts, and third in wins. Throughout his career he maximized his potential and played at a higher level than many thought possible.
He currently is in the financial services business. He has been married to his wife for nine years and has three children Noa age 6, Ruby age 4, and Stella age 1.
Congratulations Gregg and welcome to the Madison Athletic Hall of Fame!
Jerry Bruening
Jerry Bruening
Athlete
Class of 1983
Wrestling, Football & Track
Jerry Bruening is a proud 1983 graduate of Daniel Hand High School. He is being inducted into the Madison Athletic Hall of Fame for wrestling and his devotion to America. His journey from being an outstanding athlete at Hand to graduating from the United States Military Academy at West Point and serving as a captain in the Army reflects a rare combination of accomplishments for Madison and our country.
Jerry served honorably in Operation Desert Shield and Desert Storm as an executive officer in Field Artillery and he was awarded the Bronze Star for exceptional meritorious achievement recognition of distinguished service within a combat zone.
Jerry began his wrestling career at age seven when his father enrolled him in the local Madison recreation program. The program was started by two new young teachers and coaches Warren Miller and Larry Ciotti (MAHOF 2013). Mentored not only by the coaches, but also by student instructors Carmen DelVecchio and Steve Curtin (MAHOF 2014).
In Jerry’s junior year, he won the Class M state Championship in the 126 weight-class. He was a leading contributor when Hand won the 1982 State Championship as a team. As a senior, he was elected team captain and led the Tigers to an undefeated, 18-0 championship season, with Hand ranked as the #1 wrestling team in the state in 1983. That year, Jerry placed second in 126 weight class in Class M.
Jerry also committed himself to Hand’s football team. While he saw limited playing time on Strong Field, he quarterbacked the offensive practice "demo squad" for three years. He was a team player that embraced his role by contributing to three state championship finals and a state championship victory in his senior year. Jerry’s dedication, desire and fortitude were apparent as he was a three-sport athlete in football, wrestling and track. He captained not only the wrestling team but also the track team while competing in the 3200 and 5000-meter races. In his senior year, he was named male scholar athlete.
After his brilliant military career, he went on receiving his MBA. He is now an engineer for an industrial tool company. Jerry is married to his wife Kandee and he has a stepson, Jay.
Please welcome Jerry Bruening to the Madison Athletic Hall of Fame a supreme athlete, a patriot and a defender of United States freedom.
Joseph Demichelle
Joseph Demichele
Athlete
Class of 2012
Football & Wrestling
One of the most prolific careers in Connecticut high school wrestling history began when an interested father of a fellow wrestler, Brian Onofrio, stopped by the Demichele’s home to ask if Joey would be interested in giving wrestling a try.
He was in fifth grade and already involved in football, so he had to think about it. He decided to give it a try and the rest, as they say, is history. Joey grew up being taught daily by his father Ed, a former boxer and football player, to get tougher and challenge himself.
Joe credits his dad and former youth coaches like Faz Bagnoli (MAHOF 2017), Ed Brunt, and Mike Ciotti (MAHOF 2019) with adding to that toughness. He recounted a moment when after an especially difficult practice, Faz took him aside and told him that he was proud of him for sticking it out because, "the world doesn’t give you anything you have to earn it!" Those words, and others just like them, put Joe on a course that would take him to the top of the mountain in two sports when he reached Daniel Hand in 2009.
Joe is one of a handful of players to start as a freshman on the varsity football team. At 275 pounds he was a force on the defensive line and occasionally would carry numerous defensive players into the end zone as a fullback. His size had kept him from playing football in eighth grade and he was eager to get going.
For the next four seasons, Joe would anchor one of the best defenses in hand history starting in 46 consecutive games, two State Championships, and ending his career with a 34-10 win versus New Cannan in the State Championship game at Rentschler Field capping a perfect 13-0 season and the #2 ranking in Connecticut. That year, he was voted for All SCC, CHSCA All State, NHR All State, and to the prestigious Walter Camp All State team. He scored a TD in one of Hand’s’ biggest wins over Masuk in the semi-final game that year dragging several bewildered defenders into the endzone.
After competing in his senior year, he accepted a full scholarship to play football at the FCS level for Central Connecticut State University.
The wrestling career that began back in fifth grade with Mr. Onofrio’s visit also went well. Joe started and competed in every match for his 4 years at Hand. He ended his career with a 158-12 record in the unlimited weight class.
During those four seasons, he was the SCC champion three times, the Class L State Champion twice, the State Open Champion twice, and the New England regional champion.
In his sophomore year, he took sixth place in the Nationals, and seventh place in his junior season. Those two finishes earned him consecutive All-American honors. This record of accomplishment makes Joe Demichele the winningest heavy weight wrestler in the history of Connecticut high school sports!
Joe currently lives in North Haven and is a conductor for Amtrack Railroad. He will be married in October to his fiancée Katty McGovern.
Congratulations Joe Demichele and welcome to the Madison Athletic Hall of Fame!
Kara McHugh Vickerman
Kara McHugh Vickerman
Athlete
Class of 2012
Lacrosse, Basketball & Soccer
Kara was born in New Britain, Connecticut and moved to Madison in 2001. She left for a short time but returned in 2005 and soon began participating in Madison youth sports.
Soccer was her first sport activity starting early on while basketball, softball and lacrosse started later. After soccer, basketball began to become a favorite of hers, playing and practicing with Dad in the backyard. Kara played Madison travel soccer and basketball through grades 5-8. While attending OLM in Madison she began to play some softball as well. She had become involved with multiple sports early on, but lacrosse still was not one of them!
Lacrosse didn’t start until her freshman year at Daniel Hand. Under Freshman Coach Hibbard, and playing defender, she began to really enjoy lacrosse and it soon became her favorite sport to play. She began investing a lot of time into lacrosse and even got to the point where she would bring her lacrosse stick to basketball practice to work on improving her stick handling.
She was a three-sport athlete at Hand playing soccer, basketball and lacrosse. She was a three-year varsity starter in soccer and lacrosse and four years in basketball.
A few high school moments she remembered were when in soccer she scored a goal off a corner kick received from teammate, Kendra Lena (MAHOF 2025), and in lacrosse during her junior year she received a yellow card against Cheshire and it ignited her to score numerous goals that help beat Cheshire.
Kevin Siedlecki, her high school coach (now the Southern Connecticut University Girls Lacrosse Coach) said, "Kara was an amazing athlete with incredible ability to enjoy the work of improving. She first picked up a stick her freshman year, and by the middle of the season, she was messing around with two balls and a stick in each hand, throwing the balls back and forth and trying to catch them."
Early that summer, her mom called Siedlecki and asked "What can I have her do this summer for lacrosse? She’s breaking the siding playing wall ball against the chimney!" She loved playing and loved competing in all three sports. That’s why she was a three-sport captain at Hand and a two-time captain for her DI lacrosse team.
Here are some of her High School Accomplishments;
Lacrosse:
• 117 Goals and a 60% shooting percentage
• 28 Assists, 145 total points, 114 Draw Controls
• Played 47 varsity games
• Named First Team All-State, First Team All-SCC and First Team All-Area in both her junior and senior years.
• Selection: Recognized as a member of the Super Junior Team in 2011.
• Leadership: Served as the team captain during her senior year.
Multi-Sport Achievements:
She was a prominent three-sport athlete in Madison, CT, serving as a captain for all three of her teams as a senior:
• Soccer: Earned All-SCC honors and was named the team’s MVP in her final season.
• Basketball: A four-year letter-winner for the Tigers.
She played lacrosse with Nor'easter, a statewide premier program which helped her get notice for college recruiting. UMass, Marist and Ohio State showed interest, but she wanted to be sure she would play and wasn’t worried about the school's rankings. During her high school junior year, she committed to Marist where she played all four years. While at Marist, the team won four straight MAAC Championships and three regular season championships.
Kara McHugh had a record-breaking four-year career as a midfielder for the Marist Red Foxes from 2013 to 2016. She became one of only three players in program history to reach both 100 career points and 100 career draw controls.
At Marist, here are more of her accomplishments;
• Captain for two years.
• Played in 66 career games and started 52.
• 99 career goals, 42 assists, total points 141.
• Three-time All MAAC Honoree.
• Two-time First Team All MAAC.
After college, she spent a year in corporate finance but then decided to get back into the Lacrosse game when she had an opportunity to become an assistant coach at Fairfield University. She worked in the position for five years and felt that experience really made her better in life.
She currently lives in New Haven with her husband Connor Vickerman. They were married on June 27, 2025.
Kara and Connor actually met at OLM in Madison and were friends. Not until 2021 at a New Year’s Eve party did they take the friendship to a more serious level. Kara has recently taken a new job in health technology and her husband works in business development.
We congratulate Kara and welcome her into the Madison Athletic Hall of Fame!
Kim Simonsen Ickes
Kim Simonsen Ickes
Athlete
Class of 2006
Gymnastics, Track & Field
A 2006 graduate of Daniel Hand High School, Kim Simonsen Ickes distinguished herself as a standout two-sport athlete in gymnastics and track & field, setting five school records across the two sports and was named the 2006 Athletic Director’s Award as the top female athlete.
In gymnastics, she competed in all four events beginning her freshman year and was voted MVP by her coaches for all four of her varsity seasons. She earned New Haven Register All-Area honors, All-Southern Connecticut Conference honors and All-State honors all four years while leading the team to Divisional State Titles in 2003 and 2006 and Southern Connecticut Conference titles all four years.
Gymnastics head coach Steve Redes (MAHOF 2016) said, "She overcame obstacles, requirements, that others back away from. Without tumbling in a backward direction, Ickes was a consistent contributor to team scores with her all around. She was like a quiet sergeant. She did what she could with a great disposition. [She] face[d] her inability to go backwards [by using other] requirements harder than most athletes."
"I still remember the first time that I saw Kim; I went with Steve to watch recreational classes," said Melissa Arms (MAHOF 2014), both assistant and head coach during Simonsen’s reign. "Steve and I saw her immediately because of the incredible muscles that she had on her. You couldn’t miss her as she ran around the gym flipping and swinging on the bars. We knew that she had to be one of the first gymnasts at his [Steve’s] new gym.
As a junior, Ickes tied the beam record with a 9.55, a record that stood until 2024. In 2006, as a captain, she was the SCC balance beam champion for the second year in a row, and SCC All Around Runner-Up. That same year, the team continued its success all the way to the New England Championships where the team placed third. Simonsen won three individual event medals to lead the team. Her gymnastics career culminated with a trip to the National High School Gymnastics Championship event.
"Ickes overcame obstacles with hard mental and physical work, work she carried out while helping and supporting others," said Redes. "A great example of a teammate. This put Simonsen in a position of leadership often behind the scenes, and she may not even know the role model she was."
Ickes athleticism led her to being a multi-event standout beginning her freshman year on the DHHS track and field team. While she began her career as a sprinter and, in relays by her junior year, she had added in the heptathlon event. Ickes earned All-SCC and All-State honors in multiple years qualifying for States and State Opens in the 100m, 200m, and the 4x100m and 4x400m relays. Her performance in the 200m as a sophomore at the State Open earned her qualification in that year’s New England Track and Field Championship. Ickes received the "Best in Track" award her sophomore and junior seasons and served as a captain her senior year. She graduated as the record holder in the heptathlon and 100m, 200m and 100m hurdle events.
"I remember her as the hard-working top sprinter of the team," said track and field coach Tim Geary. "20 years later she still ranks 4th all-time in the 100m & 200m."
"She did all of the different things in high school between gymnastics, track and field, clubs, and band. I remember she was one of the most involved students that I had ever met and I wondered how she did it all," said Arms.
Ickes continued her athletic and academic career as a sprinter at Division I Lehigh University, where she competed in both indoor and outdoor track as a freshman. She competed in the 55m and 200m dashes for indoor and 100m, 200m and 4x100m relay for outdoor track. In 2007, she qualified for the Patriot League Indoor Track Championships. She graduated from Lehigh in 2010 with a degree in Business Information Systems.
Ickes has returned home to reside in Madison with her husband, Ken, and her sons Cameron (12) and Ryan (9) and currently works for RTX Corporation in Farmington, one of the largest aerospace and defense manufacturers in the world.
Congratulations and we welcome Kim into the Madison Athletic Hall of Fame!
Jack Callaghan
Jack Callaghan
Athlete
Class of 2009
Football, Basketball & Baseball
Jack Callaghan was a gifted three sport athlete at Daniel Hand High School, excelling in football, basketball, and baseball. In basketball, he made history as the first freshman ever to start on the varsity team at DHHS. He went on to start all four years and served as a team captain as a senior.
In the spring of his junior year, Jack joined the baseball team and immediately became a starter, holding that role through his junior and senior seasons. Football, however, was his premier sport.
During Jack’s four years, Hand football compiled a 27–16 record. His sophomore season was particularly memorable: the team went undefeated until a narrow 34–30 loss to New Canaan in the State Championship, finishing 11–1. Jack was an outstanding receiver, holding the all time school record for receiving yards in a single game. His impact on the program earned him a place on the DHHS All Decade Football Team for 2000–2009.
Across his Hand career, Jack earned an impressive nine varsity letters. His competitive spirit, leadership, and warm personality made him a popular and respected student both on and off the field.
Jack makes his home in Guilford with his wife, Taylor, and their three daughters: Hadley (5), Brynn (2), and Raegan (almost one). He still jumps into town league basketball and softball whenever he can, and he never turns down a chance to play a few holes of golf. Jack’s passion carries over into his career in sales with Angi, where he loves what he does and the people he serves.
Congratulations Jack and welcome to the Madison Athletic Hall of Fame!
Jason Dobrinick
Jason Dobrinick
Athlete
Class of 1994
Basketball & Baseball
Jason Dobrinick Is a multi-sport athlete from the Daniel Hand High Scholl Class of 1994. Jason was a highly decorated basketball player and team captain his senior year.
During his career, he was voted Middletown Press All Shoreline Conference Team in 1992-1993 and in 1993-1994, Shoreline Times All Conference Team 1993 and 1994, and New Haven Tip Off Club All-County selection.
Jason was a great scorer and rebounder while averaging 20.9 points and 9.6 rebounds per game in his senior year of 1993-1994. He had a career high game of 35 points in his senior year and went on to receive a four-year basketball scholarship to Alfred University
Jason’s baseball career was equally prolific. Jason was a co-captain of the baseball team his senior year. He received All-Shoreline Conference accolades as a pitcher in 1993 and 1994. As a senior, he was a unanimous pick for All-Shoreline Conference.
Jason was selected to the Baseball All Star Festival as a senior. During his junior and senior years, Jason had an impressive 17 win against only four losses while having a 1.83 earned run average over those two seasons.
He also led his team to winning the Shoreline Conference Championship in 1992 and 1994.
Jason and his wife Robin live in Maine and have two children, Jonas (age 19) and Cam (age 17). Jason is Director of Sales for Dechra – East Cumberland, Maine. Jonas was a swimmer in high school and also played basketball while Cam plays basketball and lacrosse.
Congratulations Jason and we welcome you into the Madison Athletic Hall of Fame!
Justin Spain
Justin Spain
Athlete
Class of 1991
Football & Baseball
Justin Spain was a standout two-sport athlete at Daniel Hand High School and one of the most accomplished quarterbacks of his era.
A three-year starter for the Tigers in football, Justin began his varsity career as a sophomore wide receiver, scoring five touchdowns before taking over at quarterback for his junior and senior seasons. With Justin behind center, the Tigers compiled an outstanding 18-3 record.
The defining moment of his career came during Hand's run to the 1989 Class MM State Championship. In the title game against Darien, Justin delivered one of the great championship-game performances in Hand football history. In the first half alone, he completed 11 of 13 passes for 226 yards and three touchdowns, helping lead the Tigers to a 34-28 victory and the state championship.
Justin earned All-Conference honors in both his junior and senior seasons and capped his Hand football career by being named All-State as a senior. In 1990, he also set what was then a Hand school record by passing for 271 yards against Bunnell. He finished his career with 2,402 passing yards and 19 touchdown passes.
Justin was equally accomplished on the baseball diamond. A three-year starter at catcher, he was a two-time All-Conference selection, batting .424 in one season and .388 in another, while hitting six home runs during his Hand career. During his three varsity seasons, Justin also helped lead the Tigers to two Shoreline Conference Championships, further establishing himself as one of Hand's outstanding two-sport athletes of that era.
His athletic career continued at the University of Richmond, where he competed in both Division I baseball and Division I-AA football.
Following college, Justin built a successful career in medical sales spanning more than 25 years. Today, he serves as Business Development Director for RestoPros of Northern Virginia, where he is helping his brother—and fellow Madison Athletic Hall of Fame (2025) member—Stephen McIntyre build and grow the restoration company.
Justin has been married to his wife, Olivia, for 26 years, and they are the proud parents of two children, Mikaela and Gavin.
Tonight, we recognize an outstanding two-sport athlete, an All-State quarterback, a state champion, and a member of the Daniel Hand High School Class of 1991.
Please welcome to the Madison Athletic Hall of Fame — Justin Spain!
Terri Ajaski
Terri Ajaski
Exemplary Contributor
1999 – Present
It is with great pride that we recognize Terri Ajaski for her outstanding dedication, professionalism, and unwavering commitment to the student-athletes and athletic community of Daniel Hand High School.
A graduate of Central Connecticut State University with a Bachelor of Science degree, Terri has built a remarkable career centered on service, compassion, and excellence in athletic training. Since 1999, she has served as the Athletic Trainer at Daniel Hand High School, becoming one of the most respected and trusted figures within the school community.
Throughout her career, Terri has provided care and support for student-athletes competing at freshman, junior varsity, and varsity levels across all sports. Her impact reaches far beyond injuries and rehabilitation. She has been a calming presence during difficult moments, a mentor to countless students, and an essential part of the success and safety of Hand athletics for more than two decades.
Terri is a long-standing member of both the National Athletic Trainers' Association and the Connecticut Athletic Trainers' Association. Her professional accomplishments include being recognized as the Training and Conditioning Most Valuable Athletic Trainer and serving as a trainer for the Connecticut All-Star Football Game. She has also generously dedicated her time and expertise to numerous Madison youth sports events and camps, positively impacting generations of young athletes in the community.
Known for her tireless work ethic, Terri has spent countless evenings, weekends, and long days ensuring student-athletes receive the highest level of care and attention. Her commitment has earned the appreciation and gratitude of students, parents, coaches, colleagues, and administrators alike.
While her list of accomplishments is extensive, Terri would likely say her greatest reward has always been the heartfelt thanks and appreciation from those she has helped throughout the years. Her compassion, professionalism, and dedication embody the very best of Daniel Hand athletics and the Madison community.
We proudly honor Terri Ajaski for her years of exceptional service and lasting impact on the lives of so many student-athletes and families.
Congratulations Terri Ajaski and we welcome you to the Madison Athletic Hall of Fame!
Mike Callaghan
Mike Callaghan
Athlete
Class of 2009
Basketball & Baseball
Coach Bill Barker, (MAHOF 2013), considers Mike Callaghan one of the top ten players ever to wear the Daniel Hand High School (DHHS) basketball uniform. His talent was recognized across the state and his list of honors reflects that excellence including: two-time All-Hammonasset, New Haven Register All-Area, New Haven Register Second Team All-State, New Haven Tap-Off Club All-Area and CHSCA Senior All-Star Game participant.
At DHHS, Mike was the star of his junior and senior seasons, leading the team in both scoring and rebounding. Under his leadership, Hand reached the quarterfinals of the State Tournament twice. He earned Team MVP honors in both seasons and served as captain as a senior.
Mike also joined the baseball team as a junior and senior and earned a starting role both years — a testament to his athleticism and versatility.
Mike continued his basketball success at Wesleyan University, where he starred all four years, earned two All-NESCAC selections, and captained the team as a senior.
Mike capped off his remarkable basketball journey with a three-season professional career in Europe, playing in Ireland and Spain.
After pro ball, Mike shifted gears to B2B tech sales and has spent the past decade working with a range of startups. He’s now settled in Boston, MA, where he spends his downtime exercising, reading, and rooting for the Red Sox. His competitive basketball days may be over, but he still sneaks out to shoot around — just to make sure the jumper still works.
Congratulations Mike Callaghan and we welcome you into the Madison Athletic Hall of Fame!
Colby Confer Shannon
Emily Jablonski
Gregg Nappo
Jerry Bruening
Joseph Demichele
Kara McHugh Vickerman
Kim Simonsen Ickes
Jack Callaghan
Jason Dobrinick
Justin Spain
Terri Ajaski
Mike Callaghan