City of Tallahassee to interview finalists for city attorney position

Tallahassee City Attorney Cassandra Jackson.
Tallahassee City Attorney Cassandra Jackson.

Tallahassee city commissioners will interview four finalists — two internal candidates and two external — as they seek to replace City Attorney Cassandra Jackson, who resigned in November.

The candidates are:

  • Blueprint Attorney Susan Dawson.

  • Interim City Attorney Amy Toman.

  • Gadsden County Attorney Clayton Knowles.

  • Duval County School Board Chief Counsel Ray Poole.

Jackson quit amid turmoil when City Commissioner Jeremy Matlow called out Deputy City Manager Wayne Tedder on social media, releasing text messages Tedder sent to another attorney, belittling Jackson's legal expertise.

Commissioners will interview the applicants 2 p.m. Tuesday in City Hall. It's not clear whether they will make a hiring decision right after the interviews or at some time in the future.

Here's more on each finalist:

Amy Toman

Before becoming interim city attorney, Toman served as deputy city attorney under Jackson.

She has over 30 years of legal experience working at multiple law firms, having served as a senior attorney for the Florida Agency for Persons with Disabilities, legislative analyst for the Florida Senate, several positions for the Florida Department of Business and Professional Regulation and executive director of the Florida Elections Commission.

She graduated from Boston College and got her law degree from Loyola University School of Law. She also received her public manager certification from Florida State.

Susan Dawson

Dawson, the other internal candidate, also boasts nearly 30 years of legal experience, including working in several law firms.

She was the senior attorney and deputy general counsel for the Florida Office of Insurance Regulation, a senior attorney at the Florida Supreme Court, and assistant general counsel for the Florida Department of Management Services. She has been the Blueprint attorney since 2019.

She's a graduate of the University of Southern Mississippi and the University of Florida's Levin College of Law.

Clayton Knowles

Knowles has the least amount of legal expertise, at 14 years. He's a Florida State alumni, having gone there for undergrad and law school.

He's worked as the Gadsden County Board of County Commissioners' attorney since 2020. Before that, he was the city attorney for Jacob City, in Jackson County, and worked at a local law firm.

Ray Poole

With nearly 35 years of legal experience, Poole has worked in several positions across North Florida. He has worked in the Office of the Attorney General and was a partner at Jacksonville-based law firm Constangy, Brooks, Smith & Prophete.

He also was chief of legal services for the Nassau County School District before becoming chief legal counsel for the Duval County School District in 2022.

Arianna Otero is the City Solutions Reporter for the Tallahassee Democrat. Contact her via email at or on Twitter/X: @ari_v_otero.

This article originally appeared on Tallahassee Democrat: Who are the finalists in the running for Tallahassee city attorney?