Will Winter Park Conduct Searches for New Top Manager and Attorney?

City Manager Randy Knight says he will retire in January and recommends Michelle del Valle to take the role.

April 7, 2026

By Beth Kassab

Winter Park City Commissioners will take up two major hiring decisions on Wednesday: a new city manager to replace Randy Knight, who is retiring after 19 years as well as whether or not to renew a contract with Kurt Ardaman and his partners at the Fishback Dominik law firm, which has represented the city since 2015.

In a letter dated April 1, Knight, who has worked for the city for a total of 35 years, announced he would retire on Jan. 8 and, in a separate memorandum, recommended Assistant City Manager Michelle del Valle to take over the job.

Knight’s early 2027 retirement has been expected for years and, as early as a 2022 succession plan, he named del Valle as his chosen successor. She has served in the assistant role since 2008.

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Michelle del Valle

As part of the plan, del Valle spent time overseeing every department in the city over the past four years to help for the role.

She holds a bachelor’s degree and a master of public administration degree from the University of Central Florida and spent 16 years working at the city of Maitland before arriving at Winter Park City Hall.

“I do strongly believe that if I get hit by the proverbial bus, Michelle is already ready to lead this great city,” Knight wrote in the 2022 succession plan.

He said in the memo to the city commission that the reason for asking the commission to finalize his recommendation this month — nine months before he will retire — is because city rules require the city manager live in Winter Park.

“Ms. del Valle currently resides in Maitland and has begun looking at houses in Winter Park,” he wrote. “Before she makes an offer on a house, it would be helpful for her to know she has been selected by the city commission to be the next city manager.”

Knight earns more than $274,000 in the role.

City commissioners could approve Knight’s recommendation and begin negotiating a contract with del Valle or they could opt to conduct a wider search and consider additional candidates for the job.

The commission, which spends between $500,000 and $650,000 a year on the city attorney contract, will also decide whether to put the contract out to bid for the first time in 11 years or to approve a pay increase for the Fishback Dominick firm.

The firm, which also represents other local cities such as Winter Garden, Ocoee and Belle Isle, is asking for increases to its hourly rates. For example, lead attorneys would charge $325 an hour, up from $275.

The commission can decide to approve the higher rates or to put the job out to bid and ask for proposals from other firms.

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