Coach Jack Simon’s legend endures across generations

By Kevin Eickman

Coach Jack Simon has been a fixture in the Milford Athletic Community for nearly 50 years.

He arrived in 1976 as a Driver Education teacher for the high school. But Milford also got a coach with enthusiasm, heart, character, and integrity. Since that time, with a few breaks in between, Simon has been the heart and soul of Milford Football and other sports.

A native of Warminster, Pennsylvania, Simon attended Archbishop Wood of the highly regarded Catholic League. A three-year varsity letterman as an offensive tackle, Simon would be a captain his senior year and was named first team All-Catholic.

When it came time to selecting a college, the choice came down Drexel University or West Chester State College. He chose West Chester, which turned out fortuitously as Drexel would drop football the following year. Once again Simon excelled in football, even being named West Chester MVP Offensive Lineman of The Year, and more importantly being named to the then “Little All-American” team.

Following graduation, Simon was offered the opportunity to teach and coach at Milford, and immediately embedded himself into coaching, assisting in track, wrestling, football and even golf.

“I love this community. Everyone looks out for each other, everyone cares, I just can’t believe how lucky I was to have landed here. Sometimes fate deals you more than you deserve, and I can honestly say that moving here has been a blessing in more ways than I could have imagined.”

Simon has coached his son Jack Jr in Pop Warner and watched his wife Bonnie coach their daughter Kelly at Milford in field hockey. Thinking that he was done with coaching, Simon was mistaken. When Mike Tkach was named Milford head football coach in 2002, he began looking through the files and found Simon’s name and wanted to speak with him.

“It started out as just helping out a bit, but before you knew it I was knee deep into coaching again.” Simon said.

It would be the beginning of a wonderful journey that would culminate in Milford Football’s greatest moment, the 2008 State Division II Football Championship. It was a special team, as Simon coached the offensive line with arguably the best running attack in Delaware. “That group was so special and so talented, they had learned from the players that came before them. Everybody knew their jobs, they weren’t afraid to be good, it made such a difference,” he said.

In the Championship game, Milford would battle Henlopen South foe Laurel. The stands on the Milford side were packed and loud

“It was amazing,” he said. “I honestly have no idea who was in Milford that night, because it felt like the whole town was in the stands. This wasn’t just about a football game; this was about pride in the community, a community that really cares about each other. You can’t put a price on something like that. I’m so proud to have been just a small piece of that great night.”

Tkach clearly holds Simon in high esteem.

“He isn’t just a football coach, he is so much more than that, Tkach said. “He is an educator, a friend, a pillar of the community. I honestly can’t offer enough praise for him. He is one of the finest human beings it has been my pleasure to know.”

After Tkach left Milford and the coaching staff changed, Simon was finally out of coaching and says he was content to help out at various athletic events and to work with The Lions Club, which gives so much to the community

Or so he thought.

When Jed Bell came to Milford as head football coach and athletic director in early 2023, one of the first calls he made to was to Simon. Having played for Simon, he knew Jack had the mindset to mentor him. It would not be long however, before Simon was again on the sideline working with the offensive line. This past season, Simon had a difficult task with a young line that included mostly juniors, sophomores and a freshman or two. It didn’t matter to Simon.

“I think the group we had this year was very talented, he said. “I loved coaching them. There is some real talent on that line, and I can’t wait to see them progress.”

Bell said he was thrilled when Simon joined his staff.

“It has been really amazing to come full circle with Coach Simon,” Bell said. “I respected him when I was a player and respect him even more now that I am coaching with him. He is the same person today as he was when I was playing for him. A teacher, and the type of person who is going to get the best out of you both as a player and, more importantly as a human being. It is an honor to work with him and count him as a mentor and friend.”