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Drake has always been distant with both of his siblings. He is not friends with either of his parents, but very close with his grandmother, Vivian Pleasant.
Drake was the third sibling to leave his parents' house with Marilyn being the first and Ian being the second. He met Astrid Wolff, the third cousin-once removed of Thornton Wolff and they married. They decided they only wanted one child, and she gave birth to Michael Pleasant. Had Michael been a girl, he would've been first in line to ascend to Vivian's throne, but instead Florence Pleasant was born and became the heiress apparent. Drake is very distant from his family and tried to make Michael act the same, but Michael refuses.