January 27th, 2023

Michael Alessandra, a 2017 graduate of Wethersfield High School, has always had football in his blood. 

When other kids were watching cartoons and coloring, Alessandra was studying football on television and dreaming of a career on the field.

“I told myself that this is what I wanted to do,” said Alessandra, who started playing the game at the age of six.

A decade and a half later, Alessandra’s dedication to the gridiron has landed him a college coaching job in Massachusetts where he will serve as an assistant coach –– coaching the running backs –– at Anna Maria College this fall.

His latest destination marks the second time that Alessandra’s football journey has come full circle. 

After four seasons playing at WHS — culminating with a standout senior season when he led the team in receptions as a tight end and starred as a versatile defense end — Alessandra then played a season at Anna Maria, starting nine games at tight end before he made the difficult decision to step away from playing the game because of a series of injuries. 

Upon his return to Connecticut, Alessandra began coaching youth football in Wethersfield while attending Central Connecticut University as he worked on a degree in education. 

He eventually reunited with his former defensive coordinator at Wethersfield, Matt McKinnon, who had taken over as the head coach at WHS and brought Alessandra on as an assistant coach. 

McKinnon said he could see Alessandra’s potential when he first started coaching him nearly a decade ago.  

“Mike has a true passion for the game of football. He was a great player who understood how to play the game,” added McKinnon. “It was no surprise to me when he reached out to be a part of the coaching staff.”  

In his first year back at WHS, Alessandra coached the Eagles freshman team an undefeated season. 

He spent the last two years working as the offensive coordinator for the varsity team, joining fellow WHS-graduates Jimmy Malizia and Johnny Orsini as former players that have returned to the school to become part of McKinnon’s current coaching staff.

During his two seasons leading the Eagles’ offensive attack, the team average over 22 points per game and produce multiple all-state athletes. This past season, the team made the playoffs behind a punishing run game that churched out 235 yards per game on the ground.    

Alessandra credited McKinnon with building a winning and welcoming culture at WHS that gives the team, the coaches, and the players the best chance to succeed    

“I owe that man everything. He builds his staff up like he does his players.” Alessandra said of McKinnon. “He holds us to high expectations, but he wants what is best for us and what is best for the program.”

Alessandra added that the experience he gained under McKinnon, both as a player and coach, made his drive to continue a career in football even greater, saying, “Matt puts in more time and does more for his players and coaches than anyone that I’ve seen in Connecticut High School football.”   

Because of that, Alessandra said his decision to leave his hometown was a tough one.

“That conversation with Matt was hard. He is my brother and those guys are my brother,” added Alessandra. “Matt does everything the right way and Wethersfield Athletics does everything the right way. I give them a lot of credit for where I am now. They support their coaches and support their kids, and they have the community behind them.”

Alessandra also noted that he couldn't have asked for a better group of kids to coach during his time in Wethersfield, coaching many of the players their entire football lives from the youth ranks through high school.

His experience in Wethersfield is a great springboard for his next challenge, where he will be joining another mentor in Massachusetts, working under head coach Steven Croce.

Croce was the offensive coordinator the season that Alessandra played, serving as an assistant for four year and earning the Eastern Collegiate Football Conference (ECFC) Assistant Coach of the Year in 2021 before taking over the program in 2022.

Croce also has several ties to Connecticut, living in Cheshire and having coached football around the state including a pair of seasons as the head coach at Coginchaug Regional. 

In his first season leading the Amcats football program at Anna Maria, Croce led the team to winning record, the team’s second straight.

Alessandra will start his new coaching position in the fall as he begins working on his master’s degree in counseling and psychology in Paxton, Mass.

McKinnon believes that Alessandra has the drive it takes at the college level.

“The sport of football has a lot of demands to coach it the right way; it is a 12-month job with the program. Mike knows the commitment and time it takes to coach football. He has the intrinsic motivation to continue to grow as a coach, learning each year to make teams better,” added McKinnon. “He will be very loyal to the staff at Anna Maria and give the players his best every single day. He is ready to take on any challenges that come his way. I am very proud of him.”

For Alessandra, the next step is another chance to further the football flame.

​“I’ve learned so much under Matt and I think I am ahead of the game but at the same time you can never learn too much, there is always something else you can learn,” stated Alessandra.  “I’m excited to see what the overall college experience is like and what else I can learn and take to the next step. I just want to keep growing as a coach.”