H-F superintendent Scott Wakeley is retiring

District 233 Superintendent Scott Wakeley’s upcoming retirement will be made official at the school board meeting on Tuesday, April 16. He will step down in June 2025.

The board is expected to approve a contract on Tuesday with The Alma Group to conduct a search for the next superintendent who will begin the 2025-26 school year.

Scott Wakeley

Wakeley came to Homewood-Flossmoor High School in 2021 as superintendent-elect, and he then moved into the superintendent’s office in 2022 following the retirement of Von Mansfield, who served as H-F superintendent for 14 years.

Wakeley told the Chronicle his retirement comes after a 34-year career in education, 21 years of those as a superintendent. The first time he was named a superintendent he was 36 years old. He’s now 56.

Wakeley has two years left on his contract, but he believes this is the right decision.

“It’s certainly not a money issue. We have enough and we’re really fortunate and blessed,” he said.  

“It’s one of those things where I’ve been doing this for a long time, and if I had anything I could do over I wish I would have been at H-F 10 years sooner,” Wakeley said. “It’s just one of those things where school has always come first” but now he believes is the time to prioritize family first. He has three adult children and two grandchildren.

“In conversations with the family this is an opportunity to go out on a high note because I love H-F, I love doing what I’m doing, but we can put the family first because we can. Why do we continue to put the family second when you don’t have to?”

Wakeley said he’s certain the school board will find the right person to fill the superintendent’s position.

“I struggled with a little, I don’t know if it’s a thing, retirement guilt. I talked to a lot of people about it and I also recognized as soon as my chair quits spinning someone’s going to sit in it and finish the work,” he said.

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