Let’s be honest: when you think of New York City political families, you probably picture the Kennedys—all pearls, sailing, and tragic glamour. Then you remember Bill de Blasio. And you chuckle.
Bill de Blasio, the 109th Mayor of New York City, ran his household like a reality show where nobody signed the contract. The cast included his wife, Chirlane McCray, and their two kids, Dante and Chiara. Buckle up.
The Patriarch: Bill, the Human Dad-Joke
Bill de Blasio is a man who looks like he once auditioned to play a depressed scarecrow in a community theater production of The Wizard of Oz. He stands at a towering 6’5”, which is mostly awkward pauses and policy platitudes.
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One of his signature achievements? Ordering the New York Police Department to stop chasing bikes after a 2014 incident. Yes, the mayor of the most dangerous city (in his telling) once told cops, “Don’t run after bike thieves.” He called it “the de Blasio way.”
He also famously takes the subway to work, which is adorable—except his security detail usually clears the car first. Nothing says “man of the people” like having a dozen armed men politely ask commuters to evacuate your train car.
Chirlane McCray: The Poet Laureate of Policy
Let’s talk about Chirlane. She’s a poet, a writer, and the real boss of the family. Bill once said, “Chirlane is the one who tells me what to do,” which is the most honest thing he ever said as mayor.
Chirlane turned her role into a full-time gig: First Lady of New York City’s mental health agenda. She launched “ThriveNYC,” a $1 billion program to cure everyone’s sadness. It was like throwing a Brinks truck of cash at a therapy couch and hoping no one asked for receipts.
Bill de Blasio, family moving to NYC's Gracie Mansion
The program spent millions on yoga classes, meditative apps, and hiring 3,000 mental health workers. By 2020, critics said it had little measurable impact. But hey, you try making a city of eight million people less angry. That’s like trying to teach a cat to use a blender.
Dante: The Meme That Became a Man
Ah, Dante de Blasio. If you remember one thing about the de Blasio family, it’s that glorious, 17-year-old Afro. In 2013, Dante stood beside his dad and gave a speech about stop-and-frisk. The internet melted.
Suddenly, Dante was everywhere: on late-night shows, in memes, even on a T-shirt that said “Dante for Mayor.” The kid was an accidental celebrity, like a pug who wandered into a fashion show and stole the runway.
But Dante grew up. He went to Yale, studied political science, and later worked as a data analyst for the Democratic National Committee. He also got a haircut. Tragic. The Afro became a cautionary tale: never get a haircut when you’re viral.
Bill de Blasio's Wife, Chirlane McCray, and Daughter, Chiara de
Chiara: The Wild Card
Then there’s Chiara de Blasio, the younger sibling who decided chaos was a family tradition. In 2016, she posted a video on Instagram openly struggling with depression and substance abuse. It was raw, it was brave, and it made her parents look simultaneously supportive and slightly panicked.
Chiara later dropped out of college and started working as a model and activist. She once shared a photo of herself wearing a “Free Palestine” t-shirt while her dad was mayor—because why not add international diplomacy to Sunday brunch conversation?
She also dyed her hair purple for a while. Not the usual color for a mayor’s daughter at United Nations events, but hey—it’s New York. No one blinked.
The De Blasio Home: Like Your Family, But With More Security
Imagine family dinner: Bill is chewing on a policy paper, Chirlane is reading a poem about anxiety, Dante is fact-checking everyone, and Chiara is live-streaming the whole thing on TikTok. That’s the de Blasio household.
Bill de Blasio: New York City mayor enters presidential race - BBC News
They famously held a press conference at their Brooklyn apartment to announce that their cat was gone. The cat, Mittens, ran away. Bill publicly asked New Yorkers to “keep an eye out.” The NYPD eventually found the cat. That’s police overtime for a feline.
One reporter asked if they’d use “Stop-and-Frisk” on the cat. Bill did not laugh. Chirlane definitely laughed. Some jokes write themselves.
The Surprising Fact No One Believes
Here’s the kicker: the de Blasios once lived in Vermont. Yes, before Bill was mayor, the whole family packed up and moved to a rural cabin for a few years. Bill wrote a book. Chirlane baked bread. Dante built a snowman. It was Little House on the Prairie meets Brooklyn Nine-Nine.
They moved back to New York because “Vermont was too quiet.” Translation: Bill got bored not having anyone to argue with at 3 a.m. on Twitter.
New York City Mayor Bill de Blasio Lands in Italy With his Family for
And when Bill left office in 2021, he didn’t exactly fade away. He immediately ran for Congress (lost). Then he ran for the New York State Assembly (also lost). The man is like a Boomerang in a cheap suit: always coming back, but nobody asked for it.
The Legacy: Weird, Wonderful, Impossible to Explain
The de Blasio family is a glorious train wreck of good intentions, bad haircuts, and one very famous Afro. They were messy in a way that felt almost refreshing. No one accused them of being boring.
Bill’s approval rating at the end of his term was around 33%, which is roughly the same as “getting a root canal.” But you know what? The family never pretended to be perfect. They were just … the de Blasios.
So raise a glass—or a cat carrier—to the most accidentally entertaining family in New York political history. They’re gone now, but their memes live on forever.