VIRGINIA- Brian Masterson was still settling into his new office in Virginia when he sat down with the Timberjay last week, but it didn’t take long to determine one thing about the new St. Louis County Schools superintendent.
The photograph of Target Field behind his desk offered the first clue. A Minnesota Twins logo hung on another wall, and Masterson happened to be wearing a Twins shirt.
“Huge Minnesota Twins fan, even when they’re not doing well,” he acknowledged.
The office may be new, but Masterson, who officially took over the district on July 1, did not arrive in northern St. Louis County as a stranger. His family has had a cabin on Myrtle Lake near Orr since at least the 1960s.
“I grew up in the Proctor school district, Pike Lake area, and spent a lot of time up here in Orr,” he said. “Many, many, many days, summer and fall, in the Orr area.”
Masterson began considering education as a career while attending Proctor High School. He credits several teachers and principal Bruce Watkins with influencing him, but sports provided his first opportunity to work with young people.
“Right out of high school, I was able to start coaching junior high levels and working my way up in the football program at Proctor,” he said.
Masterson played football and basketball in high school, along with baseball and golf. He entered UM-Duluth intending to become a pharmacist, but found mathematics a better fit and turned instead to education.
After completing his teaching degree in December 2001, he began his career the following month as a long-term substitute math teacher in Mora. Walking into an established classroom midway through the school year was intimidating for a new teacher barely older than some of his students.
“It was mine, but it was someone’s class who had just been there for half a year and had built all these relationships with kids, and what was I? 22, 21?” he said. “So it was a little nerve-wracking walking in and starting midyear, but I think very lucky, too, because at that time jobs were a little bit more competitive and harder to find.”
Masterson next joined the newly opened Andover High School, where he taught math and coached ninth-grade football and basketball before becoming head coach of the girls golf team.
“It was like the perfect fit,” he said. “It was math and then obviously got to coach three sports I played in high school, too.”
Andover also brought Masterson together with his future wife, Jenny, a special education teacher who coached cheerleading.
“I was a football coach, she was the cheerleading coach,” he said. “And we’d take some bus rides to away games and got to know each other.”
After two years at Andover, Masterson returned to teach math and coach at Proctor. While he enjoyed both, he began thinking about how he might have a wider influence on students and the people teaching them.
He again looked to Watkins, the Proctor principal he had admired as a student.
“I felt as an administrator I could do some more things to help kids or help teachers help kids, and just wanted to get more into those leadership opportunities,” Masterson said.
After completing his master’s degree and principal licensure through St. Mary’s University, Masterson became high school principal at Hinckley-Finlayson. He remained in that position for 11 years before becoming the district’s superintendent in July 2022.
Those years helped shape an administrative philosophy centered on communication, accessibility, and visibility.
“I think the biggest part is being available, being available for staff, for students, for parents, having an open door,” he said. “We may not always agree on whatever the topic is, but I really think if you have strong communication and you have clear communication, you can get through a lot of misunderstandings or disagreements.”
For Masterson, being available also means leaving the office and attending the games, concerts, and other events that bring schools and communities together.
“You’re engaged not just during the eight-hour, 10-hour workday, but you’re out in the community, supporting businesses, supporting the students, supporting the events happening,” he said. “I believe then they also see you’re not only bought in, but you’re seeing the other side of the community, what the kids are involved in, what the parents are seeing.”
One student from his early years as a principal remains particularly memorable. The student was experiencing difficulties at home, struggling at school, and sometimes getting into trouble. Because Masterson was responsible for enforcing the rules, the student initially wanted little to do with him.
Masterson began looking for something they shared.
“I tried to find some commonalities with that student,” he said. “It was football in this case.”
The discipline issues did not disappear, but the common ground changed the conversations. Rather than beginning every meeting with a report of something the student had done, Masterson would talk with him about football. Even when they had to address something difficult, he tried to end by discussing an interest important to the student.
The student eventually graduated and thanked Masterson. Years later, he returned to the school as a parent, and Masterson saw him again at parent conferences during his final year at Hinckley-Finlayson.
“And he still hugs me,” Masterson said. “I won’t necessarily call it a friendship, but there’s that respect on both sides. But, you know, we had to get through it. I had to take the time to get to know him and him me. We certainly still had some days where we didn’t agree with each other.”
Masterson announced his departure from Hinckley-Finlayson last fall before he had another position lined up. He and Jenny believed the time was right for a new chapter, and he wanted his district to have ample time to select a successor.
“I wanted to be respectful, especially since they gave me a chance as principal, then as superintendent,” he said. “I didn’t want that to possibly come down to March, April, where they were then scrambling to find their next superintendent.”
ISD 2142 hired Masterson in February. Although he was still working at Hinckley-Finlayson, he began attending district meetings in person and virtually and making visits to learn about the people, programs, and challenges he would inherit.
The transition is significantly different from becoming superintendent at Hinckley-Finlayson, where he already had 11 years of experience within the district. ISD 2142 brings multiple schools spread across the state’s largest geographic school district.
“Here, it’s kind of a brand-new fresh start,” he said. “So I’m trying to catch up on all the things as quickly as I can so I can offer support or help where I can.”
Masterson knows that learning the district will take time, but patrons should expect to see him doing it from outside the superintendent’s office as well as within it. He said he intends to attend school events and listen to people discussing both the district’s successes and its problems.
“I want to have those conversations about what’s going well or not as well so we can work together to do what’s best for kids,” he said.