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.Continue reading: Like a Prayer“The problems with my dad started after our mom passed away,” Ciccone said. “We had a lot of nannies, and they all tried somehow to take advantage of him. The last one, he ended up marrying, and he is still married to her to this day. The only problem was my siblings and I hated her guts. She was only 12 years older than me; it was like your older sister becomes your mother. This was the main reason Madonna left home. She got a full scholarship from the University of Michigan, and she left for New York to be a starving artist. She did that in part to fulfill her dream, but in part because she couldn’t live at home anymore. My dad almost got a heart attack when he heard she was dropping out of college, but it turned out to be the right move.”Until the 1990s, Ciccone’s life was pretty normal. In 1993, while he was living in L.A., his only son was born. “I really liked being a family man,” he said. “I waited for it my entire life. My wife and I were together for seven years. She was the love of my life. After the birth of our son she got depressed. I worked in Hollywood, a tough physical job, long hours. I came back after an entire day and found her still in bed after she did nothing all day long. Then we started to fight; one day she just took our kid and took off. She got a restraining order against me. I got depressed, lost my job, started drinking, and my family, my brothers, and my father stopped talking to me because they accused me of all of that. I had no support, even though I was the one who tried to make it work again. Today she is married to some new guy, and I haven’t seen my kid since 1999. I went from being a full-time family man with a car, a house, and a wife to being homeless on the streets of L.A. I lost a part of myself there, with all the things I witnessed. I saw people get murdered, women get raped, horrible things. I guess you can call it education, but I don’t wish anybody to get that kind of education.”After a long period of estrangement, Ciccone and his father’s relationship improved, he said, and Tony decided to let Anthony join the family vineyard. “For a long time, I worked there. I learned how to make wine, how to treat the vines, the whole deal. There was a time when things went pretty well; my father took me on a tour and told me, ‘Son, someday all this will be yours.’ So I asked him, ‘You mean all of that is going to be Mario’s, right?’ Mario is my stepbrother, who for some reason my dad preferred, but he told me, ‘No, it will be yours.’ Well, who’s running the vineyard today? Mario. And where am I? On the streets.”His father’s choice wasn’t just professional, Ciccone said. Anthony was deep into his alcoholism, and one day, Tony found him passed out with an empty bottle of wine in his hand. “I remember my father’s voice. He looked at me and said, ‘Well, I think that Anthony is done for today.’ Since that day, he has not allowed me to work in the vineyard again. He wanted me to go to rehab, and I said no. He’s hard on me. I’m hard on him. We don’t get along; we can’t agree on anything. After I left the vineyard, I couldn’t find another job. I didn’t have any money to pay my rent, and I couldn’t stay at my parents’ place, so I moved to the street.”Tony Ciccone declined to be interviewed for this article. (Madonna’s publicist, Liz Rosenberg, did not reply to repeated requests for comment, while a rep from her agency said, “Liz does not comment on anything regarding Madonna’s brother.”) But someone who is identified as a close family friend and neighbor, Kathy Meteyer, working in the wine-tasting room, told the Daily Mail that Tony is heartbroken about his son’s situation: “He did work here, they found things for him to do in the cellar, there’s all kind of work on a daily basis, in the summer there’s all kinds of pruning and picking to do. But he would sneak into the cellars and he would lay on the floor, open up one of the big tanks and drink the wine, with a glass. He just can’t come back until he stops drinking, because they think it will kill him; it already kind of has.”***The oldest of eight siblings (one died in infancy), Anthony is two years older than Madonna. He keeps a close relationship with his sister Paula (“she’s my buddy,” he said), but he and Madonna are not close. “I have a lot of respect for my sister’s success. She started from nothing and made her way to the top. I never asked her for anything, and I never will,” he said, when we asked him about why he never sought help from his wealthy sibling. “It’s her money; she earned it. Why should she give it to a stranger?”In the 1980s, he said, he did have a relationship with his younger, cooler sister. “I remember that I went to visit her when she lived in a loft in SoHo before it became fashionable,” he recalled. “I show up at her doorstep and I’m looking like Joe Dork. And I was supposed to eat in a restaurant with her. She looked at my clothes, she looked at me, she goes: ‘Maybe we’ll go on the roof and order Chinese.’ And we did. And it was great.” He last saw Madonna, he said, two years ago, at the Super Bowl in Indianapolis where she performed. (He was sent there by WKLT on a promotional stunt.) He didn’t have enough money for a ticket, he said, so he sat in the parking lot with a friend and drank beer. When he looked up, he could see his sister on the Jumbotron.While Ciccone’s not particularly a fan of his sister’s music, or of pop music in general, he does have a favorite Madonna song. “There is one song that got condemned in the ’80s by the Vatican. I like that song. ‘Like a Prayer.’ You know that song?” he asked. Ciccone started to sing spontaneously, in a voice that sounded like a combination of Madonna and Johnny Cash. “ ‘When you call my name it’s like a little prayer. I’m down on my knees, I wanna take you there.’ I like that song,” he continued. “Because it means something to me.”His dream was to go back to work at his father’s vineyard, but he said his stepbrother clearly didn’t want him around. Otherwise, he said, “I hesitate to dream because when you dream you get your hopes up. And then you get your heart broke. And so when this happens so many times you hesitate to dream.” He would like to get married again and have a family, but he said he knew that the odds were against him, given his situation. “I pray for one more chance, but the truth is that there is a good chance I’ll never live to witness that day,” he told us. “No one will be surprised if I’ll die before my 60th birthday. Neither will I.”***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Adi Gold is the New York bureau chief at Yedioth Ahronoth. Tal Miller, a former speechwriter for the IDF's chief of staff, is a writer for Yedioth Ahronoth.