Before that, he worked as a freelance journalist, volunteered for campaigns, and headed Mayor of Cleveland Dennis Kucinich’s housing rehabilitation office for three months.

[2] While a student at Blair High School, Cole led a walkout protesting the Kent State shootings by the Ohio National Guard in 1970.

That same year, he led a group shouting and firing cap guns into a meeting of conservative school board candidates.

On January 4, 1986, Cole was hired as a legislative aide by Richard Alatorre, who had been elected to the Los Angeles City Council.

[5] On May 4, 1992, Cole was named the Mayor of Pasadena, succeeding Jess Hughston, who was his history teacher while at Blair High School.

[8] In July 1998, Cole was appointed as the city manager of Azusa, California, chosen by the council from an applicant pool composed of mostly bureaucrats.

[10] In March 2000, Cole was investigated for criminal vandalism after covering up a billboard for the Los Angeles Avengers that had sexually suggestive text which read "Six Beautiful Women Will Show You Their Panties".

[13][14] On January 2, 2004, Donna Landeros, the city manager of Ventura, California, resigned, citing a lack of support from council members as the reason for her departure.

As city manager of Ventura, Cole prioritized visionary goals over code enforcement and construction details, a strategy that drew criticism from some councilmembers.

[20] On April 18, 2020, Cole resigned from his position as city manager of Santa Monica, citing divisions over budget cuts because of the COVID-19 pandemic.

[21][22] During the 2022 Los Angeles City Controller election, Cole supported Kenneth Mejia, who was running against political veteran and councilmember Paul Koretz.

[25] On May 10, 2023, Cole announced his candidacy for his former City Council seat in 2024 to succeed Felicia Williams, who was running for the California State Assembly.