What attack vector is a password with high entropy protecting against? The only one I can think of is an unreported database leak. The attacker may be able to more easily reverse the password hash and use your account on that particular service, at least until the leak becomes discovered and the service does a full password reset.
While it would be ideal to defend against that attack, I think it's far more important to stress that users have a different password for every website. The real attack vector that we see every day is a DB leak from a poorly secured website, passwords cracked, and then reused on important services. That's where the problem lies, not in the user's password entropy.
Jeff isn't wrong here, he's just attacking a relatively unimportant problem.