Back when she joined the force as a civilian, Cindy Pontoriero never set out to make history. As she made it clear many times when interviewed early on, she did not do any of this to be a trailblazer or to be the face of a movement; as she famously stated in one interview, "I wasn't doing it for women's lib." She just wanted to be a cop. And that she was.

Her journey began in 1960 as a civilian stenographer. Her natural sharp mind and command of the work did not go unnoticed, and by 1967, she was encouraged to take the exam, earning a promotion to policewoman, where she started in the Youth Division. From there, due to her natural police instincts, she was added to the 1st Division Tactical Unit, working plainclothes to deal with shoplifting and pickpocket rings on the city streets.

In 1971, Cindy made history. For the first time, women were allowed to take the competitive detective’s exam. Cindy, alongside more than 2,100 candidates, 99% male, she placed in the top 3% and noted as the highest scoring female. With that score, she was the first female promoted to Detective in the history of the Chicago Police Department, making her the true first female detective ever for the Chicago Police Department. Just four months later, she took her place in Homicide…the job she always wanted.

It was during these years on the force that she met her husband, another Chicago Policeman, Iggy Grimaldi. The two were married in May of 1974. Together, they built a family, welcoming their first son, Lary, in September of 1974, followed by Dominic in May of 1976.

Once her family was settled and the boys were well into elementary school, Cindy chose a life of leadership. She rose to Sergeant in 1985 and then to Lieutenant in 1990. She commanded districts across the city with integrity. She finally landed in the 17th District (Albany Park), where she spent her final years on the job serving as Watch Commander. She was a disciplined but fair leader while being a trusted mentor for the officers under her charge.

In November 2004, after 44 years, part civilian and mostly cop, Cindy retired exactly as she lived: on her own terms, "quietly," and with zero fanfare. She left behind a legacy etched into the very soul of the department, built not on what she did as a detective, but on the friends she made and her absolute devotion to the job.

Cindy was preceded in death by her beloved father, Hilary Pontoriero; her beloved mother, Erna Pontoriero, her brother, Charles Ponti; her beloved husband, Ignatius Grimaldi; and her niece, Gretchen McLaughlin.

Her legacy lives on through her loving family. She is survived by her devoted sons, Lary (Bridget) and Dominic (Bree); her cherished grandchildren, Dominic, Maggie, Nora, and Ella; her sister, Theresa (Michael); her nieces, Candice (Gordon) and Melanie (Trey); her nephews, Charles and David; along with many dear cousins and extended family.

Cindy served her city proudly, protected her community, and loved her family fiercely. She was an officer’s officer, a true leader and mentor, and will be always be a legend of the Chicago Police Department. Her watch has ended, but her story will never be forgotten.