WALDOBORO — On April 3, Medomak Valley High School Assistant Principal Andrew Cavanaugh’s head will be shaved, the result of losing a bet he never expected to win. 

Students at the school are filling a donation jar of money to support Principal Harold Wilson as he battles a rare liver cancer, a cancer that only 4 percent of those diagnosed with liver cancer get. Staff members are doing the same with a jar of their own.

The wager? If the student jar accumulates a greater value than the staff jar, Cavanaugh will allow his head to be shaved in front of the student body. 

The donation challenge, however, has been rigged. Teachers have been padding the student jar, and a donor in Friendship contributed $500 to the student effort, as well. 

The shaving will take place at the next student-of-the-month assembly. Many will be wearing green T-shirts that express school solidarity. The National Honor Society students will wear green rubber bracelets. Green is the color of liver cancer awareness.

But, that’s not all. 

Cavanaugh will be joined by 14 male staff members, all determined to have their heads shaved, as well, in a show of support for their beloved principal. (One female staff member offered to shave her head, but was persuaded otherwise.)

Wilson is a Mainer. He grew up in Port Clyde (his father ran ground fishing boats), fished out of there, attended the University of Maine in Orono, then returned to Medomak Valley as chemistry teacher, assistant principal, and now principal.

Under his leadership, the school has created an advanced placement program, and an enrollment program with Thomas College.

“The rigor of instruction has increased substantially and the options for kids has increased substantially,” said Cavanaugh.

The percentage of students graduating from the high school also rose under Wilson’s tenure.

His greatest legacy, however, is his multiple pathways approach to learning. Every decision he makes is guided by the question,’ What is best for kids?’

That philosophy put him at odds with some in the community, but not with staff and students.  Wilson makes the attempt to know every kid, and by their senior year, Wilson knows them by name.

According to Cavanaugh, each student can relate to Wilson at any level, from his undergrad in civil engineering, chemistry, lobster fisherman and son of a sardine fisherman, community member and family man.

Wilson, nicknamed Smiley, is married to Jolene. Together they have three sons, Anthony, a consultant in Washington D.C.; Loukas, a merchant mariner; and Josiah, a tutor within the Medomak Valley district (and like his father, he is a lobsterman). He also has one granddaughter, ‘Sunny.’

According to Cavanaugh, Wilson is proud to have his cancer and bile duct tumors diagnosed last month by a physician who was a former student from Wilson’s chemistry days. 

He is proud to have recognized a nurse and two technicians at Pen Bay Medical Center, all Medomak graduates.

Wilson is loyal to Medomak Valley High School, and staff and students are loyal to him.

“He’s the best boss I’ve ever had,” said Cavanaugh.

“They don’t make them any better,” said Steve Ocean, special education coordinator, as repeated by Cavanaugh.

Medomak Valley High School is hosting a spaghetti supper fundraiser for Wilson, April 8 in the cafeteria. Businesses and individuals are welcome to donate towards funds for Wilson.