[3][4] Ryan and State Representative Terry Van Akkeren challenged incumbent Juan Perez in the 2009 mayoral election.
He annexed land for a future business center along I-43 near the University of Wisconsin–Sheboygan/Sheboygan Area Lutheran High School campus that was named "Willow Creek Park.
"[7] Ryan worked with city's Director of Development and Planning to form the Sheboygan Market District to promote regional foods.
[8] In December 2009, former City of Sheboygan Human Resources Director Angela Payne filed a complaint with the Equal Rights Division of the Wisconsin Department of Workforce Development alleging sexual harassment and racial discrimination.
[12] Ryan said the firing was the result of numerous department heads approaching him, detailing Payne's shortcomings in a meeting and asking that she be terminated.
[12] An equal rights officer with the Department of Workforce Development who investigated the complaint found Payne's allegations of sexual harassment credible, recommending a formal hearing before an administrative law judge.
[26] He reached a plea agreement of a lesser charge of operating with a prohibited alcohol concentration in July 2013; he received a fine and had his driver's license revoked for eight months.