Nathan Stubbert owned three businesses, worked as a promoter for the entertainer Gallagher, and chose college over a shot at the pros after a strong high school baseball career.

All those experiences, along with studies that included an administrative internship at then-Wiscasset High School, have prepared the Waterville man for his new job as assistant principal for grades 7 through 12 at Wiscasset Middle High School and athletic director for grades 9 through 12.

He has thrown his hat in the ring for the stipend position of athletic director for grades seven and eight.

Stubbert has taught at the school two years and will still teach alternative education half-time. The program focuses on dropout prevention and helping students earn credits missed toward graduation. Students who enter the program may have fallen behind for any number of reasons, from difficulty learning to a problem at home, Stubbert said.

Before Wiscasset, Stubbert spent 14 years teaching alternative education at Messalonskee High School in Oakland and a half-year teaching it at Skowhegan Middle School.

Working for Gallagher helped hone Stubbert’s skills at organizing.

“It was a pretty busy job. It was fast-paced ... especially when we got to the shows and were there on location. There was a lot of stuff to deal with and it was just he and I. It was a great experience, something I’ll never forget.”

The two met when the watermelon-smashing comedian did a show at a night club where Stubbert was working during college. When Stubbert became athletic director/program director at Waterville Area Boys and Girls Club, he asked Gallagher to perform at a fundraiser for the club’s new facility. “He did, and I put the show together pretty much all by myself, did all the advertising for it, sold all the tickets. And he liked the way I did it.”

Traveling the country working for Gallagher was a blast, Stubbert said. He did it for about six years, starting in 1995. A ticket agency Stubbert ran then (Eustis Entertainment, named for his English mastiff) was one of three businesses he has had. The others were a Waterville restaurant called the Spotted Dog Tavern (referring to his brother’s dog), and Lakeside Country Market in Oakland.

The New Hampshire-born Stubbert graduated from New Hampshire College in Manchester, New Hampshire, in 1994 with a bachelor’s degree in sports management. Growing up in central Maine, he played baseball, basketball and soccer; was a Kennebec Valley Athletic Conference batting champion; and was drafted in a supplementary draft for pro baseball. But a contract would have barred the catcher from playing college baseball.

He chose college. Then came shoulder surgery. “That messed everything up ... There are always regrets, but everything happens for a reason,” he said.

Despite the shoulder issue, he had a successful college baseball career and still plays baseball; the 45-year-old is one of the oldest members on his team in a 30-and-over, wooden bat league in Winthrop.

He has coached in community and school soccer, basketball and baseball programs outside Wiscasset, from Babe Ruth to high school sports.

Stubbert received a master’s degree in educational leadership from Thomas College in Waterville in 2014, after a semester internship under then-Wiscasset High Principal Deb Taylor. Since then, he has been the school’s back-up administrator when Principal Cheri Towle and then-Assistant Principal Sarah Ricker were out of the building.

He loves teaching, but wanted to go into administration to make better use of his personality and his experiences.

“I love the ‘busy-ness’ of the position and dealing with students,” he said. “There’s a lot of teachable moments that occur in this position. I also like the aspect of being a positive male role model for a lot of the students.”

As a candidate for his new job, Stubbert excited the interview committee with his love for the Wiscasset schools and wanting to make positive changes for athletes and for all students, Towle said. “I’m really excited that (he) was chosen.”

Stubbert said he will be looking at student discipline and helping student-athletes to hold themselves to a higher standard as he has for himself; and that he plans to attend as many school sports events as possible.

“I want to be available to my coaches and to parents to talk. I’m very approachable, and I just want to make sure everybody has a great experience. High school is a time that these kids will remember forever, and I want it to be as pleasant an experience for all the student-athletes as possible.”

Stubbert’s son Brayden, 10, and daughter Brynn, 6, are both into sports. Brayden Stubbert is one of three Waterville youth selected for a free trip to Cal Ripken’s baseball camp in Aberdeen, Maryland this month, his father said.

Of all the places Stubbert has taught, he said he likes Wiscasset best.

“From the second I walked in here, I’ve felt like I was part of a family ... I’ve had opportunities here that I haven’t had in the other schools, (including) administrative work, which is what I’ve been shooting for, and everybody has treated me extremely nicely,” he said.