I don't think he's being mean-spirited in his response. It's his personal opinion and didn't put Madonna down in it.
At the time, Madonna was kind of mentoring Britney. They both wore T-shirts with each other's names. While Christina was clearly managed, I saw the Britney-Madonna combo as Madonna caring for her and Britney greatly admiring M.
George Michael has always been incredibly particular about his collaborations and how his work is represented, sometimes obsessively. Madonna has been more relaxed about who she works with. He and Elton John often seem too precious for the common world. They might have their reasons, but a bit of humility could make them more approachable, I think.
Regarding the 'desperation' or shock value part: He made a whole music video based on being arrested in a toilet.
A fun thing to do, but he was cashing out on the tabloids and the shock of the public.