Well, since the first one went so well, I'll try again. I think you can remove the question mark, Madonna is definitely an ESTP.
According to David Keirsey, ESTPs are promoting. Madonna is not the best singer, dancer or the best-looking woman, but she is a master of self-promotion. ESTPs are often trend-setters in Sensing-related endeavors, and Madonna helped revolutionize music videos and fashion. She also did a lot to make techno more mainstream. According to Linda Berens, SPs thrive on variety. They like to try as many things as possible, especially the extroverted SPs. Madonna never stays with one style for too long, and is a risk-taker. She's tried everything, including writing children's books. I have personally observed that ESTPs often have a childlike quality about them, not innocent so much as impish. Yet they are quite calculating. In recent years, Madonna has made noticeable attempts to appear "grown-up", even changing the way she speaks, and expressing opinions on politics and parenting. I think she is a T because she is not sensitive, and she does not make any decisions for "personal" reasons. She's tough, and does not exhibit emotional devastation even in the face of adversity, unlike SFPs like Britney Spears. She fancies herself to be a woman of business, and with regard to her sexual proclivities, she's more than just free-spirited, she's aggressive. She's not at all stereotypically feminine, but does use her sex as a tool. SPs are most concerned with making an impact, and that is certainly true of Madonna. But that's the way she is with everything. She has a direct, in-charge way of interacting with people, and according to the Interaction Styles theory, that is the way ESTPs prefer to communicate.