Assuming the answer is no, there are only two remaining alternatives: 1) Someone targeted and keylogged him to obtain the password, in which case it doesn't matter how strong the password is; or 2) Someone hacked iCloud itself and stole their (presumably unsalted) password file.
In that case, yeah, a stronger password might've helped. Bad user. No cookie.
But if he thinks he's having a rough night, consider what scenario #2 would mean to Apple. The impact of an iCloud hack would be measured in multiple billions of dollars of market capitalization.