We even have AEG Live (who did this tour) but I don't think we cover the Saint Pablo tour specifically.

Acts way way smaller than Kanye get their tours insured as pretty much standard practice (not always for event cancellation which is super expensive, but definitely for things like your equipment getting smashed). It's not a surprise at all that his management/label would put out a couple insurance policies for this tour.

Anyway it would completely surprise if he was pulling a long con on this for the insurance money unless he was planning on just completely peacing out from the music industry after this and using the insurance money to pay off his debt. We've definitely had submissions come through that are completely uninsurable (Amy Winehouse and Charlie Sheen come to mind) and it definitely puts a huge damper on your ability to do business an entertainer after that point. Maybe not as much when you're basically on top of the world like Kanye but if you fall off a bit from there? Absolutely.