Jury Rejects Anne Olear Age Bias Claim Against School Board
Table of Contents
Case Background
Anne L. Olear spent more than four decades as a Family Consumer Science teacher in Waterbury, Connecticut. She began working for the district in 1974 and taught at West Side Middle School until her retirement in February 2020 at the age of 67.
Before leaving, Olear explored the possibility of returning to work under the rules that allow retired teachers to be rehired in shortage areas. She spoke with school administrators and Human Resources staff, who told her she could retire, take a short break in service, and then come back under a new contract. Based on these conversations, she formally submitted her retirement paperwork in February 2020.
Soon after, the school district posted her position. Olear applied and interviewed. The school principal even wrote to HR that he wanted her back. Yet weeks later, she was told another, younger teacher with less experience had been hired instead. Olear felt the decision was discriminatory and misleading.
She filed a complaint with the Connecticut Commission on Human Rights and Opportunities in February 2021, received a release of jurisdiction later that year, and then brought this lawsuit in November 2021.
Sequence of events
The lawsuit grew out of a sequence of events that began when Anne Olear decided to retire in early 2020. She had worked for Waterbury Public Schools for 46 years, but before stepping away she wanted to make sure she could continue teaching under Connecticut’s post-retirement reemployment rules. These rules allowed retired teachers to return to work in shortage areas without affecting their pensions, provided they followed certain conditions.
Olear said she spoke with her principal and with Lisa Dunn, a senior HR official, who told her she could retire, take a short break in service, and then return to her same position at a lower pay step. Based on those assurances, she signed her retirement paperwork. She believed this step was part of a formal process that would lead her back to the classroom within weeks.
But behind the scenes, according to her complaint, the district marked her ineligible for rehire, citing “insufficient notice.” Olear argued she had never been told that her notice was deficient or that she would be barred from returning. She said the district continued to let her go through the motions submitting an application, sitting for an interview, and even being recommended by her principal even though HR had already blocked her eligibility.
When the district filled the position with a younger, less experienced teacher, Olear claimed this was not only unfair but also discriminatory. She alleged her age was the real reason for the decision and that the talk of “insufficient notice” was just a pretext.
Injury
Olear said the district’s actions cost her wages and benefits she would have earned if she had been rehired. Beyond the financial losses, she described emotional harm, including distress and frustration after decades of service to the district. She felt pushed aside despite her experience and commitment.
Damages
She asked the court for compensatory damages to cover lost income, attorney’s fees, and other appropriate relief. The amount in demand exceeded $15,000.
Key Arguments and Proceedings
Legal Representation
Plaintiff(s): Anne L. Olear
· Counsel for Plaintiff(s): Anthony J. Interlandi
Defendant(s): Waterbury Board of Education
· Counsel for Defendant(s): Emily E. Cadman
Claims Asserted
Olear’s attorney argued that age was the deciding factor. They pointed out that she was qualified, had decades of experience, and even received support from her principal for rehire. Yet the district chose a younger candidate with fewer credentials.
They also emphasized how Olear relied on assurances from HR when she filed her retirement notice. The district told her she could come back but then marked her ineligible internally, something she did not know. Counsel described this as a broken promise that cost her financially and emotionally.
Defense Argument
The Waterbury Board of Education denied wrongdoing. They admitted Olear had been a teacher but argued that after she retired, she was not automatically entitled to her old position.
The district maintained that the job posting was not specifically “her” position but a general opening. They claimed the person hired was already an existing teacher who transferred into the role, making it a legitimate hire.
They rejected the idea that age was a factor, saying the decision followed internal processes. They also disputed Olear’s claims of misrepresentation, insisting no one promised she would be rehired.
Jury Verdict
The case went to trial in late 2024. On November 8, 2024, the jury returned its verdict.
The jury found the verdict in favor of the Waterbury Board of Education and against Anne L. Olear.
Court Document