John Pynchon

St. John's Prep

When John Pynchon returned to coach at his alma mater three years ago, he wanted to help build the program back up that he had once starred for. He knew it would take some time to implement his systems and get the players to buy into the message he was selling.

It all came together for the Eagles this spring, who went unbeaten in the Catholic Conference to win the league title, scored the top seed in the Division 1 North state playoffs and reached the sectional final before falling. Along the way, St. John's Prep went 18-4 on the season and won 11 straight games at one point (and 16 of 17 contests).

The 36-year-old from Ipswich, best described this year's Eagles as "a pleasure to coach" and was proud that after road games, his team "left the bus cleaner than we found it". They scored nearly double the amount of goals (272) that they allowed (138) and were deep throughout their lineup, with five players named to the Catholic Conference all-star team and two of them — senior defenseman Drew Leahy (First Team) and senior faceoff specialist Craig Yannone (2nd) being named to the Eastern Mass. Lacrosse Coaches' Association All-Americas.

With 12 varsity seasons as a head coach (including nine years at Beverly High) under his belt, Pynchon's teams have a combined mark of 168-84. His three St. John's Prep squads have compiled an overall 36-24 mark.

Pynchon and his wife, Liz, have a son, John and a daughter, Lillian. He thanked his coaching staff, as well as Jim O'Leary, Jameson Pelkey and Jordan Edgert from the St. John's Prep athletic staff, for all of their support this season.


Jocelyn Brault-Graham


A year ago, the Highlanders' head coach inherited a program fresh off two straight Eastern Independent League championships and took them right back to capture the title in her first season at the helm. After setting the bar high with a league crown right off the bat, Brault-Graham had the tall task of ensuring her girls came back just as strong this spring.

Not only did Pingree maintain its elite status — they improved significantly. The Highlanders (16-1) secured their fourth straight EIL title during a campaign that saw them finish three and-a-half games better than their '18 group (13-5). 

What's even more impressive than this and their spotless league mark (10-0) was their success against non-conference foes. Nearly all their losses the previous year were from teams outside the EIL circles; this time around, the Highlanders suffered just one setback as they scorched their way through the schedule.  

“As a smaller school you always want to stick it to the bigger teams, and that’s exactly what we did in our non-league games," said Brault-Graham. "They wanted to prove they belonged throughout the whole season, and it’s fitting that they’re going out as champs.”

The former University of North Carolina star has compiled a 29-6 record in two seasons with Pingree, but is hardly new to coaching. She's spent several years heading both the Granite State Elite Lacrosse and Laxachusetts lacrosse clubs as well as scattered experience at the high school level.  


Brian Crowley 


Brian Crowley's 20-year reign as the Marblehead boys indoor and outdoor track coach officially came to an end following this spring season. He admitted it was a difficult decision and that he'll definitely miss it.

Crowley has coached many talented track and field student-athletes over the years — also coaching the girls for a short time before Kylynn McKinley took over — and said the Magicians wouldn't have been as successful without the outstanding assistant coaches, who who have helped him through the years. Crowley loves the sport and his passion was passed on to the athletes.

"I have had a great coaching staff, dedicated to the athletes and support of both the athletic office and Marblehead track community," said Crowley, who is a Marblehead High history teacher. "I've had the privilege of working with hundreds of outstanding, hard working young men and women who made practice and meets the highlight of every day."

Crowley, a Danvers resident, also thanked his wife for knowing how much coaching meant to him and working around his schedule of late nights and all day Saturday meets as well as countless missed meals to give him the opportunity to coach.


Dan Connors 

Essex Tech

A year ago Essex Tech took the Commonwealth Athletic Conference girls track scene by storm, winning the league and championship meets as well as the Vocational School title. Defending those three was a tough task, but the Hawks did it once again this spring.

"This year was special because our group of girls didn't let the success of the 2018 season make them complacent," said Dan Connors, The Salem News Coach of the Year. "They came in with the same attitude and passion to defend our titles — and did just that.

"This program is filled with young ladies who really understand commitments and have dedicated themselves to making Essex Tech a state recognized program which is perhaps the most important thing," he added. "I consider myself extremely grateful to have such a rare collection of athletes."

Connors, who is also the Hawks' football coach, has been the girls head track coach for three years, the past two with perfect 10-0 league records. He thanked coaches Dan Verrington, Chris Roumeliotis, and Emily Ouellet for their assistance.

A guidance counselor at Essex Tech, Connors and his wife Danielle live in Revere.


Julia (Witzig) Deleskey

Essex Tech

The Hawks had a very successful season despite being a young team with some freshmen starters. Deleskey guided the team to a 14-6 record, a Commonwealth Athletic Conference co-championship, the Vocational Tourney semifinals and the Division 2 North playoff quarterfinals.

The Peabody resident, who grew up in Rowley, has coached the team for the past three years and is a teacher at Essex Tech. She's been coaching for the past nine years and was previously the softball coach at Masconomet. 

Deleskey scheduled some non-league games with strong teams that only made her squad better. The team chemistry was great and the veterans helped the younger girls fit right in.

"We had a young team and there was so much potential. They all loved to compete," she said. "The team was a family, and the girls never settled. They wanted to get better each day."

Deleskey thanked the players for their commitment, her varsity assistant coaches Greg O'Brien and Emily Pontes, JV coach Deb Xenos, and Ashley Hersey, who works with the freshman program. She also thanked her family and athletic director Farah Lalli.


Joe Maher


Another high school spring tennis season, another coaching honor for Joe Maher. 

For the second consecutive season, Maher has been named both the Cape Ann League boys tennis Coach of the Year and our Salem News boys tennis Coach of the Year. And when looking at his team's results, it's hard to disagree with either selection. 

This particular season — Maher's 22nd at the helm — his Generals went an impressive 15-4, won yet another CAL Baker Division title, and made it all the way to the Division 3 North semifinals before bowing out under unfortunate circumstances to league rival Amesbury.

The successful campaign put Maher's career coaching record at a staggering 271-84. 

"It was a great season and overall we probably over-performed all season," said Maher. "We had some clutch performances at times this year, too, which was great. These kids really worked hard, so I'm really proud of this team."

Maher helped produce a pair of First Team CAL all-stars this season in Michael Seger and Robby Donovan, and was once again a great friend and mentor to the entire group. 


Gardy O'Flynn


The Tigers' girls tennis squad might not have won many matches this spring — four, to be exact — but it certainly wasn't due to a lack of effort or coaching. 

In just his first year at the helm, O'Flynn was able to get an overall young and inexperienced group of athletes to buy in to his tactics and have fun while doing it. The result was an inspired level of tennis that set the stage for the program for years to come. 

"We had a great group of seniors who came out on the court ready to work and improve in any role," said the 48-year-old O'Flynn, a former pro baseball player from Ipswich. "Mixed in were some freshmen that were able to win matches at the varsity level. It was good to see different girls step into unexpected roles and contribute as the season went on."

Those talented freshmen included first singles standout Anastasiya Kozak and the doubles tandem of Ava and Ella Borgman, the former of which garnered Salem News all-star status. In addition, O'Flynn — who took over a team whose one win the previous year came via forfeit — was named the Cape Ann League's Co-Coach of the Year for his impressive inaugural campaign. 

While O'Flynn spends much of his days on the baseball diamond as a pitching coach, it's clear that tennis runs in the family and he feels a connection to the game. His son, Declan, just graduated from Ipswich High after a phenomenal tennis career that saw him go undefeated as a senior. 

A physical education teacher at Ipswich, O'Flynn also has two daughters, Aubrey and Tess, and another boy, Aidan, with his wife Claire.


Russ Steeves 

Bishop Fenwick

Every Bishop Fenwick baseball team that's won a North championship has benefited from having Russ Steeves around. If you spend much time with the Crusaders' head coach, you know that's no coincidence.

A player on Fenwick's '85 state champs, an assistant coach on the '04 state champs and now head coach for the 2019 Division 3 North titlists, it was the steady hand of Steeves that guided this year's Crusaders through pitching injuries that would've derailed most clubs. The veteran coach knew exactly which players to convert to pitchers and just when to call on them when the flow of the game would give them the best chance for success.

The results speak for themselves: Fenwick's 18-8 record was tied for the program's most wins in 15 years. The Crusaders won 12 in a row, sweeping through the North playoffs with come-from-behind wins over Saugus, Swampscott and Lynnfield before falling in the state semis.

"We had six seniors and we considered them all captains. We trusted them, used their input on a lot of things. They were our leaders and really guided us. I was lucky to coach them," said Steeves, who was assisted by Adam DeBaggis, Chris Renzulli, Mike Gaigle and Mark Campbell.

In six total seasons as head baseball coach, Steeves boasts an 89-47 record with a impressive 9-5 mark in the playoffs and three Catholic Central League titles.