There is probably some truth in what you say but I think Andy Gray is used to playing this charade and they probably have a joke about it afterwards. It was mainly Keys' behaviour that got them the boot at Sky but despite that they have stayed together since (first Talksport before BEin).
From the clip with Nicky Summerbee, it appears Keys (or more likely one of the producers) has scrolled social media for the points he put forward. Full of well-worn clichés and none of it make any sense.
If you follow the "logic" ... if Pep won the same amount of cups as Heynckes the season afterwards he would still be a failure because it was all done before, ditto Barcelona because all the cups (apart from the Club world cup) had been individually won before.
Beyond just talking bollocks as filler, they probably also have a remit to say stupid things (like the Allardyce comment) to get publicity for BEin on social media. And to be fair it works judging by the amount of posts in this thread and the twitter posts being shared.