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Madonna’s Homeless Brother Dishes on the Pop Queen’s Childhood Passover Seders

Exclusive footage of Anthony Ciccone singing his sister’s hit ‘Like a Prayer’: ‘It means something to me,’ he says

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Anthony Ciccone, 2013, and Madonna, 2011. (Photoillustration Tablet Magazine; original photos Adi Gold, Gareth Cattermole/Getty Images for the BFI, and Shutterstock)
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Anthony Ciccone didn’t take his shoes off once last summer. It was the first lesson he learned in the school of the streets: When you’re homeless, the closest thing to a weapon you have is your shoes. “If you try me, you’ll find out that I have strong and accurate kicks,” he said.

Ciccone, 57, who has lived on the street or in shelters for the past four years, doesn’t attract much attention in Traverse City, one of the wealthiest cities in Michigan and a base to hundreds of homeless people who wander the riverside. Ciccone has a deep radio voice and is an occasional gimmick host on a local rock station, WKLT. His sister is Madonna, an affiliation that follows him 24/7, tighter than his shoes, heavier than the plastic bag in which he carries his belongings.

While the biggest pop star in the world has a net worth of several hundred million dollars, her older brother is barely able to beg a few quarters to enable him to get some tobacco in his rolling papers. “The homeless here chase me because I’m too intelligent,” he explained. “The police chase me because they have no real crimes to handle. The media chase me because you want to hear the shit about my sister. This is why I need good shoes; there is always something to run away from.”

In March 2013, a local female police officer attempted to arrest Ciccone on an outstanding warrant for trespassing. Ciccone resisted. His mugshot made the rounds of the tabloids. He was sent to Grand Traverse County Correctional Facility for 30 days, after which he disappeared. “I have no idea what happened to him since he got out,” said Ciccone’s Traverse City lawyer who we called from New York to ask for help in finding Ciccone. “I don’t even know if he’s in Traverse City or not. I suggest that you save your time. It’ll be like searching for a needle in a haystack.”

It’s hard to overstate what Madonna symbolizes for the people of Israel. She is still arguably the most popular American singer in the land, an image that is bolstered by her fascination with Kabbalah, and her public support of the Jewish state. Like many Israelis, we had listened to Madonna’s music all our lives and felt a predictable mix of feelings about her brother’s story. How could such wealth permit such povertry? How was it possible that a brother and sister could have grown up in the same house and ended up so far apart? When Anthony popped up in the news again—and once the lawyer told us the man couldn’t be found—we decided that we didn’t have a choice. We hit the road to Michigan.

The homeless we ran into in Traverse City confirmed Ciccone’s lawyer’s concerns. “Anthony moves from place to place by foot and by bike,” they said. “He doesn’t sleep in the same place more than one night because once he settles in the police kick him out.” But a man who called himself Polish Dave, and identified himself as a senior member of Traverse City’s homeless community, didn’t hesitate: “Get me some vodka, and I’ll find him for you.” His credibility seemed shaky, but we had nothing to lose.

Polish Dave took us to one of the local churches. He went in and then came back out with both good news and bad news. The good news was that Madonna’s brother was in the church. The bad news was that he was unwilling to speak with us. We offered Dave a pack of cigarettes, and he went back in to convince Ciccone. A few minutes later, three people snuck out of the church’s back entrance: Polish Dave, Ciccone, and another homeless man named Michael—Ciccone is as experienced in losing the media as his sister is. Like papparrazzi, we gave chase. When we finally reached him, he stopped and started screaming that we should give him $10,000 or leave him alone. I said, “We came here from Israel just to talk with you.” Something in his expression changed. Three and a half hours later—after talking with him at the church, in a park, and under a nearby bridge—while sipping a beer we had bought for him, he explained why Israel mattered to him. And then he announced: “Until my mother passed away, we celebrated Passover every year.”

Passover? “Right. I know it’s strange, but my mom insisted on it,” he said. “She felt comfortable with Judaism, so we learned about the Ten Commandments and all the Jewish customs. Our Passover wasn’t kosher but it impressed me very much. I have no doubt that Madonna was affected by it and that it related to her Kabbalah studies. Both of us have a lot of respect for your country; you fight against endless enemies that want to crush you, and you don’t give up because you’ve got balls and a heart. I hope that one day I can visit the vineyards in Israel. The women, too.”


Twelve miles away from the soup kitchen where Ciccone often finds a hot meal is Tony Ciccone’s thriving family vineyard. Tony is Anthony and Madonna’s father. The vineyard was the last stop for Anthony, in his former life. It still symbolized what he said was his biggest wound—his tense relationship with his father—a wound that goes back to 1963, when his biological mother, Madonna Louise, died of breast cancer. That death was a turning point in the Ciccone children’s lives; Madonna refers to her father in many of her songs, particularly on the album Like a Prayer. The difference between Madonna and her older brother is that, while she used this open wound to create what Rolling Stone magazine called “the greatest album a pop artist can create,” Ciccone may be digging deeper and deeper into that wound on the Traverse City streets.

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Madonna’s Homeless Brother Dishes on the Pop Queen’s Childhood Passover Seders

Exclusive footage of Anthony Ciccone singing his sister’s hit ‘Like a Prayer’: ‘It means something to me,’ he says