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A Bearcat legend, Bobby Wilkins is retiring on June 30

Bobby Wilkins stands in front of the HHS logo that’s there because he insisted that it had to be. He retires after 22 years as principal, and 44 year with the school system, on June 30.

By Bill Moss, Published: March 29, 2023

Bobby Wilkins was nearing graduation day at UNC Asheville when he got a call in his dorm from Tom Wilson, the principal of Hendersonville High School.

“He called me like in March” and offered him a teaching job at his alma mater. “And I said, ‘Well, I'm going into computer science and I'm kind of looking forward to that.’ And he said, ‘I'll give you math, I know you’re a math man.’”

Wilkins told Wilson he’d like to think about it. It didn’t take him long. He called the principal the next day and accepted.

“I ended up coaching four sports that year,” he said. “I coached football, coached two basketballs and girls track that first year.”

His heart was in Hendersonville High School then, and that’s where it’s stayed throughout his 44-year career as a teacher and principal. Except for his time leading the middle school, he’s been at HHS his whole career. His last Move Up and “Hail to the Red & White” will be on June 9 before he officially retires June 30.

“My lucky number has always been 44,” he said in an interview Monday in front of the huge red HHS insignia at the new school’s entrance — there because he insisted it had to be. “The players that I loved when I was a little boy — Willie McCovey was number 44, Donnie Anderson for the Green Bay Packers — they were all 44. So it was always my lucky number. I loved it.”

Until Sept. 11, 2001.

“My 44th birthday was 9/11,” he said.

He recalls sitting in a principals’ meeting that morning when Superintendent Tom Burnham abruptly told everyone to “go back to your school. Something terrible has happened to our country.”

“My first major experience at Hendersonville High School as principal,” he said, “was living through 9/11, making sure things were OK here, and they handled it very well.”

Many state championships

A 6-5 basketball star as a Bearcat before playing guard for four years on the varsity squad at UNC Asheville, Wilkins has always been a sports fan. While he was a teacher, he coached three varsity teams to state championships— two in basketball and one in golf. As principal, “I've been around for a lot of state championships,” he said. “That's been a pleasure.”

Along with Sept. 11, any time a student has died — it happened four times during his principalship — has made for a tough experience to guide the kids through. And Covid lockdowns smothered the spirit of a lot of HHS traditions.

“I have to say it really bothers me that I'm going out with Covid,” he said. “A lot of the kids haven't gotten to experience HHS the way I wanted them to just because Covid messed ’em up.”

Another challenge that Wilkins survived, and prevailed in, was the five-year political war over the new construction-renovation project. For a while, it looked like the Board of Commissioners would approve a plan to build an all-new school and abandon or even bulldoze the historic Stillwell classroom building and auditorium.

“Well, I had a lot to say, but nobody knew it,” he said. “I made the commissioners mad a few times.”

‘Last of a dying breed’

Although distractions like the internet, social media and text messaging present a challenge, students at HHS aren’t allowed to use cellphones during the school day. When kids beg to use them during lunch, Wilkins is steadfast in saying no. They’d never make friends or learn to socialize with classmates face to face, he says.

“Everything that goes on in the world that’s different changes school. You can date back forever — when did they first get TV? We just keep going,” he said. “Kids have to learn a curve in how to handle those things and we (as teachers and administrators) have to learn a curve in how to handle those things.”

At HHS Wilkins has outlasted six superintendents — Burnham, Yeager, Page, Jones, Caldwell and Bryant. Each time one left, he knew a rung on the ladder in the central office would be open. He was never tempted to step onto it.

“The thing I have told all the superintendents is I love being around the kids. To me that's what school is about, the kids,” he said. “You come to work, you see the kids, you watch what they're doing, you see how successful they are in a four-year span. You see kids go above and beyond anything that you would ever know and you go, ‘Wow, I was part of that.’”

Former schools Superintendent John Bryant said Wilkins’ determined focus on putting kids first set him apart.

“The guy is a legend and he really is the last of a dying breed — the career principal,” he said. “Bobby is such a unique individual and not just in the state but really in the nation — somebody who says, ‘Hey, I'm going to give up myself fully to the principalship for my career as the middle school principal and high school principal.’ He's one of those people that knows exactly why things are the way that they are. As I used to tell people, ‘Bobby's seen the movie.’ He's also one of the strongest school leaders I've ever been around in terms of really making it about kids first and trying to lift that up, and being relentless in his attention to that.”

Having led HHS to many successes in his four-decade career — in academics, leadership, sports, performing arts — Wilkins, 65, says he can see education consulting on some level. But he’s in no rush to pursue it.

“Grandchildren are there to be taken care of,” he said. “We’ve got to do that.” He and his wife, Gwen, have a grandson and another grandbaby on the way in three weeks. “I know I'll find something else to do. I just don't know what.”

He’s not aware of any event to honor his career and celebrate his retirement, nor is he asking for one.

“I’ll just fly out the door on June the 30th and everything will be good,” he said.

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