He watched her seemingly self-forecasted success blossom from their youth.
"It was a double-edged sword," he said. "Nobody was chaining me down to make — to stay.
"Where there was a gift, there was also, you know, a slap, you know what I mean? So, it kind of -- it balanced itself out in some ways, but in the end. I had to step back."
Ciccone also said that his "controlling" star sister is beginning to "crack" under the pressure of turning 50, and is struggling to maintain her choreographed, mythic image.
Part of the singer's well-crafted image is her relationship with Ritchie. Currently, the Material mom is battling allegations that she had an affair with A-Rod, but Ciccone said he believes it's "highly unlikely" his sister broke up the baseball player's marriage.
"It seemed absurd to me, truly," Ciccone said.
"I think that he was interested in Kabbalah, to be honest," he said. "I doubt that this is actually an affair. I really doubt that she had any — I'm, I'm sure she had nothing to do with the breakup of their marriage."
Madonna also had to respond to months of rumors about turbulence in her own marriage to Ritchie. Tabloids have reported that she and Ritchie are on the verge of divorce.
And while Ciccone makes no secret in his book about his feelings toward Ritchie — describing him as unfriendly — he said his sister will "do what's best for her family and her kids. And I think that she'll do her best to maintain the marriage and keep it going," and he "would never advocate the end of their relationship.
"I don't think — she's not the kind of person just to walk away," he said.
Ciccone said Madona and Ritchie use Kabbalah to get their relationship through the rough patches, but he was skeptical about how effective it could be.
"I don't think that — while Kabbalah is useful, I don't know that it's the only thing that can hold something together, like a marriage," he said.
He added that the study of Kabbalah has partially benefited his sibling.
"I suppose, on some level [it has made her a better person], although I think Kabbalah, in many ways, has validated some of her bad behavior. I think — you know, now it's her way or no one's way, because she's got God on her side now," Ciccone said.
"It's again, like our relationship, a double-edged sword," he said. "You know, it can be very helpful, but she has a tendency to use it like a weapon, and I think that's not what they quite intended."
Ciccone said his sister "blackmailed" him into studying Kabbalah.
"I had finished a house for Madonna and she owed me a final payment and, you know, she, she said, you know, 'if — I'll only pay you your final payment if you come to a Kabbalah class,''' Ciccone said. "And I was like, 'if this is what it takes to get paid, fine, I'll go.' And, as it turns out, it was the perfect time for me ... to take another look at myself at the time — it was 2001. And while I resented her for, for forcing me into it, I actually got some good stuff from it."
ABC News' Chris Francescani, Michelle Major and Lee Ferran contributed to this report.