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'With his heart first'

CESD's Milt Dennison led 'gently,' say those who knew him, as he celebrates his retirement from education

REVIEW PHOTO: VERN UYETAKE - Clackamas Education Service District Superintendent Milt Dennison receives a big hug from Vickie Chamberlain.Colleagues and former co-workers gathered last week to celebrate with Milt Dennison, the longtime superintendent of the Clackamas Education Service District, who is retiring after 47 years in education.

The Review announced in April that Dennison would be leaving after serving since 2004 with the CESD, which offers services and support to 10 school districts including Lake Oswego and West Linn. On June 15, there was a slide show, a reception with cake and dozens of people who came by to wish him well before his last day June 30.

“We had a big crowd, a lot of people I haven’t seen in a long time,” Dennison says. “It was good. We had some people fly all the way from Boise, people that used to work here.”

Dennison has been an education administrator for more than 40 years and an educator since 1969. His roles have included serving as superintendent of the Camas School District in Washington and leading the Canby Elementary School District. Dennison also worked as director of curriculum and instruction and middle school principal in the six years he spent in the West Linn-Wilsonville School District, and he was an elementary school principal in the Dixon Unified School District in California for five years.

His replacement will be Jada Rupley, who is currently serving as an administrator consultant in the risk cooperative of Educational Service District 112 in Vancouver, Wash. She’ll begin her new job on July 1.REVIEW PHOTO: VERN UYETAKE - Outgoing CESD superintendent Milt Dennison poses with incoming superintendent Jada Rupley.

Dennison will continue to serve as a consultant. He also plans to visit Spain in July to visit his grandkids and their parents, and says he enjoyed his farewell get-together before easing into retirement.

“It was nice; they were all pretty positive people today,” he says.

Here’s what some of those people had to say about Dennison:

  • “Milt has always led gently, with his heart first. He’s been particularly good at reading the tea leaves and getting ahead of whatever may be coming forward in education. I have had the pleasure of working with Milt on the Teacher Standards and Practices Commission. He was the board chair there when I was on the board. And he’s always, always thinking first about what’s going to be in the best interest of kids, and that’s why he’s been a joy to work with.”

    — Linda Brown,

    Lake Oswego resident

    and member of the

    CESD board

  • “Absolutely one of the most satisfying experiences that I’ve ever had in education. He is perhaps one of the most inspiring and organized, effective people I have ever seen in education. And working with him has been a great experience. I have nothing but great respect for him and I have truly enjoyed working with him. I’m going to miss him, but we have chosen Jada Rupley, who has many of the qualities that I think he also has. I think it will be an easy transition. But boy, what a great man to work with.”

    — Len Mills,

    Milwaukie resident

    and member of the

    CESD board

  • “When I first started, Milt said he had signed up for the Boy Scouts fundraiser, rappelling over the top of the Citibank Building, the pink one that is so tall. He did it to raise money for kids.”

    — Linda Eastlund,

    CESD director of

    special education

  • “He is easygoing and dedicated, and he winds me up and lets me go. He is tireless and cares very much about the staff and the kids that we serve.”

    — Pam Bonner,

    executive assistant

    to Milt Dennison

  • “Milt was just so knowledgeable that any time I had a question, it was really easy to find out what it was all about, what was the back story and how to move forward. So, I could come in here and represent the organization well, and I really appreciate that kind of mentorship that he was able to provide to me.”

    — Pat Kaczmarek,


    specialist for CESD

    By Jillian Daley
    503-636-1281, ext. 109
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