Over the past decade, the Brookline Police Department has faced several high-profile cases involving allegations of discrimination, harassment, and retaliation. Notable incidents include the firing of Police Chief Ashley Gonzalez for sexual harassment, resulting in over $250,000 in settlements; the promotion of officers Kevin Mealy and Cheryl Molloy despite pending lawsuits alleging discrimination and retaliation; and the settlement of a racial discrimination complaint by former Officer Estifanos Zerai-Misgun for $135,000. These cases highlight ongoing challenges within the department related to workplace conduct and accountability.