Damon Dorsey was 23 and searching for a job when he stumbled upon an opening in Times Square’s security department.
More than 15 years later, every shift still brings something new. One night in late September, it was a 27-foot-tall monument.
Mr. Dorsey was there for the installation of Kehinde Wiley’s “Rumors of War,” a bronze statue of a triumphant African-American man riding a horse, atop a limestone base. Since then, in addition to his typical duties of keeping hundreds of thousands of tourists, locals, sightseeing bus ticket hawkers, Elmos and Mickey Mice from running over each other, Mr. Dorsey has been a kind of docent, explaining to anyone who seems curious or puzzled about the artwork towering above them.
His employer, the Times Square Alliance, has deputized Mr. Dorsey and several other security and sanitation workers as “public art ambassadors” for the monument, which will end its residency between 46th and 47th Streets this weekend. Before dawn on Monday, it will be removed by a crane and sent to its permanent home outside the Virginia Museum of Fine Arts in Richmond.
As Mr. Dorsey and his co-workers tell anyone who asks, Mr. Wiley’s monument is a retort to Confederate statues in general, and in particular those that sit not far from the museum on Richmond’s Monument Avenue, where the Confederate icons Robert E. Lee, Stonewall Jackson and J.E.B. Stuart all sit astride horses.
Some of the security workers volunteered for the art ambassador role, while others were asked. Marlan Saddler, another ambassador-slash-officer, said he didn’t really know anything about the artist before a few months ago. But he knows people: He’s outspoken and chatty with visitors, he said, so his supervisors tapped him.
Mr. Saddler always wanted to be a cop as a kid, but decided to try security first. Among security gigs, he added, working at Times Square is considered a prized assignment: You have to earn it. Mr. Saddler’s time came several winters ago, as a public safety officer in Bryant Park. He landed an interview after jumping in to help a man — now his Times Square boss — who broke his wrist at Bryant Park’s ice rink.
For Mr. Saddler and his colleagues, the ambassador training was minimal. Some preparation centered on the artist and how the statue was created, but a lot focused on anticipating what questions visitors would ask.
Sometimes, visitors will spot them and head over with questions. More often, the ambassadors see someone stop to look up or read the display, and that’s their chance to move in and start a discussion. They not only provide the basic details, but also try to engage people with questions: How would you describe what this work means to you in one word? If you were to build a monument, to whom or for what would it be?
The bustling scene around the statue, though, can have its challenges. Music from nearby break dancing groups can drown out conversation, and the occasional passer-by relieving himself in a potted plant can prove, er, distracting.
Still, Jean Cooney, the director of Times Square Arts — a program of the alliance, which looks after and promotes Times Square — said the ambassadors, who also include artists and art educators, have struck up 3,000 conversations.
Many visitors have come to Times Square specifically to see the piece, including the occasional Kehinde Wiley superfan — his vibrant portrait of President Obama brought Mr. Wiley wide recognition beyond art circles — and curious Virginians wanting a sneak peek at the statue that will soon be in their backyard.
International visitors sometimes ask basic questions about the Civil War. Another popular question: How much does the monument cost? (Answer: It’s not for sale.)
“I tend to forget how important art is and how it can impact a lot of people,” Mr. Saddler said. “Seeing all these people travel far just to get here, even for a day, to see the statue says a lot.”
They have special red or black jackets and badges identifying them as ambassadors. One of them, Ashley Blackmon, prefers to stay dressed as a public safety officer. “It’s easier for me to approach people in my security uniform,” she said, “because they don’t think I’m selling anything.”
They wear one hat, but it feels like two. The officers, who summon police when things get out of hand, still watch their surroundings during conversations with visitors (Mr. Dorsey calls it his “wandering eye”), and they still answer questions about the statue while in public safety mode.
The crowds have absorbed the monument into the Times Square rhythm. Break dancers flip from the statue’s base. A tourist spilled lunch all over the bottom of the monument. “One time a woman was sitting on it, and she was literally tanning,” Mr. Dorsey said. “Like, tanning. She sat all the way back, and I was just like, really?”
“I’m surprised, but I’m not,” Mr. Dorsey added, “because I’ve been here for so long.”
By the time the monument leaves for Virginia, Ms. Cooney estimated, 15 million people will have walked through the intersection where it stands.
But, she said, “just because 15 million people will have the chance to encounter it doesn’t mean that they’re stopping and having any sort of depth of engagement around it, or forging any real connection to it.”
“Or even understanding that it’s not an American Eagle ad.”
That’s where the ambassadors come in. The monument’s last few days in New York are a few more days to seek out people scarfing down hot dogs or ogling the blinding ads overhead or reveling in a newfound spot to sit, and asking them to look up.
“We want people to interact with it,” Mr. Dorsey said, and to help them “understand the significance of it in that sense where it’s a piece of history.”
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