I think that's why he mentioned using random amounts of time for disconnect and reconnect. If your malicious device guesses correctly for the simulation of "fake breaking" (let's say it only has 10% chance of doing that) and similarly for reconnecting (another 10% chance), then the malicious device only has a 1% chance of fooling the PC.
Not great, but certainly a lot better than a 100% certainty of fooling the PC.
Yep, that's what the randomness is for, and you can also add entropy by randomizing the time before the dialog starts to present he user with the "emergency connect mode instructions" which explain the disconnect/reconnect process.
Plus, 99% of the time the user is not plugging in a HID device, so the "unrecognized input device" dialog can be made ominous enough that users will realize something is very strange about that one USB stick.
Not great, but certainly a lot better than a 100% certainty of fooling the PC.