Bloomington city council picks deputy Monroe County prosecutor as new staff attorney
Bloomington’s city council unanimously hired Monroe County deputy prosecutor Jake Rossman as its new staff attorney, ending a search that began after both council lawyers resigned in February. Rossman's start date is not yet set, but is expected by mid-October.
The Bloomington city council has picked a deputy prosecutor for Monroe County, Jake Rossman, as its new staff attorney. That brings to an end a search that started after both of the council’s lawyers resigned in late February.
The unanimous vote to hire Rossman came at the council’s Wednesday (Sept. 2) meeting. The hire is contingent on the completion of a standard background check by the city’s human resource department, and a negotiated start date.
The council is hoping Rossman will be able to start as soon as possible, but that might not be until mid-October, according to council president Isak Asare’s remarks at Wednesday’s meeting.
The city council is keen to fill the position because all three positions in the council’s office are currently vacant. The three positions are administrator/attorney, deputy administrator/attorney, and legal researcher. For the last several months, they have used a former city attorney, Larry Allen, on a temporary part-time basis to fill in for some of the job responsibilities.
Rossman is currently a deputy prosecutor in the Monroe County prosecutor’s office, where he is assigned as the misdemeanor prosecutor for the Monroe County circuit court. He has worked in the prosecutor’s office since 2024.
Rossman is a 2006 Indiana University graduate with a bachelor’s degree in journalism. Before going to law school, he worked in journalism and public relations. As an IU student, Rossman wrote for the Indiana Daily Student.
Rossman received his law degree from Yeshiva University’s Benjamin N. Cardozo School of Law in New York, where he attended from 2008 to 2011. He served as an editor of the school’s Journal of International and Comparative Law.
Rossman later returned to IU, where he worked as a prelaw adviser in the university’s Health Professions and Prelaw Center from 2019 to 2024.
The council’s authority to hire its own lawyer, separate from attorneys who work for the mayoral administration, is based in state law. Bloomington has taken advantage of that authority for decades.
Dan Sherman served as the council’s administrator and attorney for about 30 years before retiring July 31, 2020. His deputy, Stephen Lucas, had worked in the council office for about nine months as Sherman’s deputy when councilmembers decided in May 2020 to offer him Sherman’s old job without conducting an outside search.
Before joining the council staff, Lucas had worked for about three years as chief deputy to Bloomington city clerk Nicole Bolden. He graduated from the Indiana University Maurer School of Law in 2014 and previously worked as an associate attorney at the Bedford firm Pittman, Emery & Nikirk. The council formally approved Lucas for the job in June 2020.
[Added at 11:16 a.m. on Sept. 2, 2026: Heather Lacy served as deputy administrator/attorney from about Sept. 2020 to April 2022.]
Lucas remained in the position until July 2024. With a search for his successor still underway, the council appointed then-deputy administrator/attorney Ash Kulak as interim council administrator/attorney until the position could be permanently filled.
Lisa Lehner was hired as the permanent council administrator/attorney later that year. Kulak returned to the deputy role. By the start of 2026, Kari Bennett was serving as the council’s deputy administrator/attorney.
That staffing arrangement fell apart in late February. By Feb. 26, both Lehner and Bennett had turned in their resignations, and the council convened a special meeting to work out how to replace them. Councilmembers also considered whether to separate the two functions reflected in the traditional slash title of administrator/attorney.
In mid-April the council had Larry Allen take over the city council’s legal work on a temporary part-time basis. Allen had previously worked in Bloomington’s city legal department, and served for a time as deputy mayor under mayor John Hamilton’s administration. More recently Allen was tapped as city attorney at the start of mayor Kerry Thomson’s administration in 2024, before leaving for private practice at the end of the year.
Rossman’s move from the county prosecutor’s office to the city also comes with a salary increase. Monroe County’s 2026 salary ordinance assigns $83,180 to the deputy-prosecutor position corresponding to Rossman’s job.
Under Bloomington’s current 2026 salary ordinance, the council administrator/attorney is a Grade 12 position, out of a maximum of 14, in the city’s salary grading scheme. For 2026, the five-step Grade 12 salary range runs from $101,411 to $131,836. Rossman’s announced salary at Wednesday’s meeting was $101,411, which is the start of the Grade 12 range.
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