Forrest Claypool
Forrest Claypool (left) says he doesn't see a solution to CPS' financial troubles that doesn't include having teachers pay more toward their own pensions. Credit: Photo by Melissa Sanchez


This week wasn’t the first time Forrest Claypool’s name had ever surfaced in discussions of a new CEO for Chicago Public Schools. In 2001, Catalyst checked in with more than 50 civic leaders to hear their ideas for a potential successor to Paul Vallas. Claypool was among them.

At the time, Claypool was vice president of management and business development for, a software firm specializing in government services like collecting fines and posting court records. Between 1993 and 1998, he led the Chicago Park District through a housecleaning to address budget shortfalls, charges of mismanagement and public discontent. During that time, Claypool displayed both a can-do management style and a thin skin in response to informed critique.

“Forrest did a yeoman’s job of turning around a system that didn’t focus on customers’ needs,” said Gwendolyn LaRoche, park district director of external affairs in 2001. Among his accomplishments, Claypool created a training center where park district staff could beef up their skills in teaching and working with children.

However, his relationship with Friends of the Parks, an independent advocacy umbrella for park district advisory councils, was not strong. At the time, park advocates told Catalyst that Claypool showed “zero tolerance” for criticism of his efforts and wrote letters to Friends of the Parks board members bashing their suggestions.

See “Utility player,” in “People’s Choice: Candidates for CEO,” Catalyst February 2001


Claypool’s appointment as CEO was paired with the promotion of former Westinghouse College Prep principal and school network leader Janice Jackson to Chief Education Officer.

Pairing a management whiz with an educational leader has been tried before, with mixed results. In San Diego, the duo of Alan Bersin and Anthony Alvarado was initially hailed as groundbreaking, but their lack of collaboration with the local teachers union ultimately killed their reforms and left political acrimony in their wake.

By contrast, former CEO Arne Duncan’s partnership with Barbara Eason-Watkins as chief education officer was harmonious and long-lasting. Eason-Watkins had responsibility for all district offices pertaining to education except planning and evaluation, which fell under Duncan’s purview. “We’re a great team,” Eason-Watkins said during a joint interview with Duncan for “City Voices,” Catalyst’s long-running radio program that was heard on WNUA 95.5 FM.

See “Top-down tactics a killer for top-notch program,” Catalyst April 2002 and “We have a chance…to be the best urban school system in America,” Catalyst August 2007


Many of the challenges Claypool & Co. will face—fiscal, managerial and educational—are perennials for which expert advice abounds. In 2003, Catalyst invited national experts in educational leadership to offer counsel to incoming CEO Duncan.

“Go deep in a few areas rather than broadly in many. Set two or three goals, not 15,” advised Thomas Payzant, the longtime superintendent of Boston’s public schools, who was widely recognized for making significant systemic improvements.

“Be somebody who knows what you know—and even more significantly, what you don’t know,” offered Michael Usdan of the Washington, D.C.-based Institute for Educational Leadership.

In 2007, Catalyst asked locals—business leaders, teachers and parents—to share their thoughts on the next phase of educational improvement in Chicago.

“The real heavy lifting is not done by do-gooders like me,” wrote businessman-turned-philanthropist Martin Koldyke. “It must be done by extraordinary principals, assistant principals and teachers who have talent and training.” (Koldyke founded two organizations aimed at high-quality teaching, the Golden Apple Foundation and the Academy for Urban School Leadership. The latter is controversial for its contracts with CPS to run “turn-around” schools.)

See “Schools chief’s job bigger than CEO’s ,”Catalyst June 2003 and “Doing good over the long haul,” Catalyst September 2007

Freelancer Maureen Kelleher's work has appeared in Education Week and the Harvard Education Letter. She was an associate editor with Catalyst Chicago from 1998-2006.

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