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The New York Sanitation Department (DSNY) swore in its first Black, female three-star chief this past New Year’s Eve.
While millions of people were in Times Square on December 31 to celebrate the start of 2024, Cherry Bailey was flanked by friends and family for her swearing in by Mayor Eric Adams and Sanitation Commissioner Jessica Tisch. Bailey was scheduled to take the oath and become the first Black woman to hold the three-star title of Sanitation Department chief: she became only the second woman to achieve that rank in DSNY’s history.
Bailey had traveled a long route to get here. She began working as a sanitation worker at DSNY in November 2005. Her first assignments were to work in Jamaica and St. Albans, Queens. She’d only taken the job because it promised job security, but when she started she wondered if she’d made the right choice. “Before I joined DSNY, I had never seen a woman on the [sanitation] truck or even doing anything sanitation related. Me, I like to have my hair done and I like to keep my nails, you know, a certain length and I like to get some polish. I like to wear my lipstick and before I came to sanitation, I didn’t want to go from that to picking up dirty, heavy, stinky, trash.”
Born in Barbados, Bailey can remember migrating to Brooklyn, New York at age 16 with her family. After spending numerous summer vacations in New York, her family moved to the city for good. She soon realized she was moving from a serene, Caribbean Island where young kids wore uniforms, to a densely populated city where kids styled themselves in the latest fashions. It was a culture shock, she said, because the way of life was truly different.
Initially, Bailey had dreams of becoming a lawyer; she wanted to make her family proud. “I knew that we came here for a different––a better life. And I was just focused on just whatever it was that was going to happen for me: I just wanted to make my family proud and not regret packing up everything and moving here and me being a disappointment to them.”
She wound up not heading toward law school, and after taking on a few jobs Bailey entered the airline industry to become a flight attendant. She said she was passionate about that job and loved the ability to travel all over. She worked as a flight attendant up until 9/11 when, with the airlines furloughing workers, she started looking to change her career, so that she could stay closer to home and be with her young son.
“I’m not going to leave the airlines unless I find a job working for the city,” she said she told herself. “Why? Because at the time, I knew that city jobs provided job security. So, I made it just my business to go out and just seek city employment.” Bailey turned to the The Chief newspaper for listings of upcoming public service exams. “I didn’t necessarily set out to take the test for sanitation. It was just another test that was being given at the time and it’s funny because I either didn’t see it or it missed my eye, but I had a friend who called. He knew that I was taking all these different exams for police officer, bus driver, train operator, train conductor, [and] bridges and tunnel officer. But sanitation was not one that caught my eye at the time. My friend, he reached out to me, and said, ‘Cherry, the job for sanitation will be opening soon.’ And I said to him, ‘What, picking up garbage?’ He said yes and I said, ‘Nobody wants to be a garbage woman!’ He laughed and he said, ‘Just take the test, take the test, and somebody’s going to call.’”
Bailey took the exam and scored really well. In fact, her scores on the DSNY and other tests had gotten her call backs. She turned down an offer to work with the police department, because with a young six-year-old son at home she wanted to be able to be with him and see to his needs. She did some provisional work as a traffic enforcement agent and then got her call to come take the physical for DSNY. Bailey passed the DSNY obstacle course test and was able to pass the state commercial driver’s license test. “By October of 2005, I was hired,” she said. “It was the best thing––well, I did not know it then, right? I did not know it then, but it was the absolute best, best decision, best thing that has happened to me in my life.”
Bailey quickly realized that she was one of very few women working in the department. Still, she said her co-workers were fine; she never felt disrespected. She was encouraged and able to rise through the ranks from supervisor to deputy chief, assistant chief, and then Queens east borough chief. Now, as DSNY’s chief of safety and training, Bailey is responsible for ensuring that all department employees have the operational knowledge to do their jobs safely and effectively.
The job is great, but so far one of her fondest memories is being sworn in to take the job in Times Square, on New Year’s Eve, by the mayor and DSNY commissioner in front of family and friends.
“I tell you; it was just a wonderful, memorable, just an awesome, can’t even put it into words… Like my commissioner, she just totally blew me away. I got the phone call: there were rumors going around in the department from my colleagues. But me, I like to wait until I hear from, for lack of a better term, the horse’s mouth. I was in tears, tears of joy, when Commissioner Tisch brought me in the office, and she gave me the wonderful news, I just couldn’t help it, because I had flashbacks of just everything leading up to the position, just all the hard work, and this dedication, and knowing where I came from, and just making my family proud, and just to now being extremely, extremely proud of this incredibly talented, hardworking group of individuals I work with.
“If you would have told me that I would one day be the chief of safety and training, I would tell you, no, I think you’ve got the wrong person. Not because I just couldn’t see myself doing it, but because I didn’t know, I just had no clue, that there’s just this whole different world here at Sanitation, that I wasn’t exposed to back then. Like I said, how often do you pay attention to that garbage truck just going through the block, and what’s happening behind the scenes?”
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