Madonna’s oldest brother, Anthony Ciccone, has died at the age of 66.

Joe Henry, husband of Madonna’s sister Melanie Ciccone, shared news of Anthony’s passing on Saturday. “Anthony was a complex character; and god knows: we tangled in moments, as true brothers can,” Henry wrote in a note posted to Instagram. “But I loved him, and understood him better than I was sometimes willing to let on. But trouble fades; and family remains— with hands reached across the table. Farewell, then, brother Anthony. I want to think the god your blessed mother (and mine) believed in has her there, waiting to receive you. At least for today, no one shall dissuade me from this vision.”

Hailing from Michigan, Anthony Ciccone was the oldest of eight siblings. Due to addiction and other personal issues, he was estranged from his family for much of his adult life. Speaking about his pop star sister in a 2011 interview, he stated, “I never loved her in the first place, she never loved me. We never loved each other.”

Ciccone worked as a carpenter, and was later employed at his father’s wine vinyard.

In 2017, Ciccone reportedly achieved sobriety and made amends with his family.