Milford’s Dave Caldwell wraps hall-of-fame coaching career

For the past 45 years, Dave Caldwell has been an integral part of Milford’s academic and athletic community.

After growing up 7 miles south in Wellington, Caldwell came to Milford to teach and coach junior high boys basketball in 1980. He took over as varsity head coach four years later, beginning the first of two stints in a 24-year head coaching career that left a significant mark on Illinois high school basketball.

His first run with Milford went from 1984 through 1998, with the Bearcats winning 20 or more games in each of his last seven seasons. His teams went 261-106 over those 14 seasons.

Then after serving as the principal at Milford Grade School for 17 years, he returned to the sidelines as head coach in 2015 for 10 more seasons. He went 187-122 over that span before retiring at the end of the 2024-25 campaign.

With a career head coaching record of 448-228, along with his many years as a teacher and administrator, Caldwell said the best part was the chance to be a part of his students' lives.

“I’m going to miss that the most,” he said. “Even when I retired from being a principal, it was difficult not being around the kids all the time. Now that I was just a coach, I still was there two to three hours a night with them.

“Now I’m not anywhere, and that’s going to be the hardest thing. It’s why I got into education. I love working with kids and coaching kids.”

Although Caldwell was more of a baseball player growing up, including playing for a couple of seasons at St. Joseph’s College in Rensselaer, Indiana, the ins and outs of basketball always interested him.

The decision to coach basketball paid off for Caldwell, with the team’s success in the 1990s remaining meaningful to him, even with all the ups and downs.

“We had a great run, had a lot of great players,” he said. “We had seven 20-win seasons in a row, but the sad part is we lost six regionals by two points or less. That was heartbreaking, heartbreaking, heartbreaking,” he said. “We had a team one year that was 25-2 and our losses were to Mahomet-Seymour and Effingham, and that was little ol’ Milford with our two losses against teams like that. I’m really proud of those teams we had in the 90s.”

As a result of that run, Caldwell was inducted into the Illinois Basketball Coaches Association Hall of Fame in 2014. Because he coached just 14 seasons, he did not qualify for the hall as a coach and was instead inducted in the Friends of Basketball category.

Once he returned as coach, and started piling up more wins, the IBCA moved to induct him as a coach in 2023.

Steve Totheroh first met Caldwell when Caldwell coached his youth baseball team in the early 1980s. Years later, Totheroh landed at Milford and joined Caldwell as an assistant coach for the basketball team’s stellar run in the ’90s.

Totheroh succeeded Caldwell as head coach after the 1997-98 season and later became principal, as well, where he hired Caldwell back on as varsity head coach in 2015. He later got to break the news to Caldwell that he was a hall of fame coach.

“That was something that he was never outspoken about that he wanted, but I do think that he was hoping for his legacy that people would recognize that,” Totheroh said. “He was a little emotional when he got that news, and it was well deserved. He’s actually been inducted twice, and if there was a third way to induct him, they would induct him.”

Caldwell said receiving the news from someone he had know for more than 40 years meant a lot.

“He brought me in one day and he set me up pretty good,” Caldwell said. “He started talking this and that, and then he read this letter from the IBCA. I get pretty teary eyed. It was nice to hear about it, especially for one of your best friends to be the guy that tells you.”

But with all the success and recognition he had over the years, Caldwell said it is the relationships he was able to build through his life as an educator, administrator and coach that mean the most.

“I’ve met a lot of people over the years, have made a lot of good friends, had a lot of good teachers that I worked with and then worked with me as a principal,” he said. “That was one of my biggest goals, finding the best teachers you could find and the kids will follow in line. They did, and I just think we had a great school there for many, many years. A lot of great kids, a lot of great teachers.”