Composite of file photos / Boston Herald
Alums of the Boston Police Department make up two of the top three city pension earners: Sgt. Winifred Cotter, seen at left in 2014, and then-Commissioner William Gross, seen in 2021. (Composite of file photos / Boston Herald) 
Winifred Cotter, a Boston police sergeant who served as a driver for her cousin, former Mayor Marty Walsh, is the top pension earner amongst city retirees, raking in nearly $16,500 a month.
