They're just your run of the mill ex-pro's who feel like they have a elevated status of knowledge just because of that. But if they do, they don't show it.
I know Merson has/had his problems away from football but I genuinely feel like Sky have kept him on out of pity. He's actually a really bad pundit - doesn't care for players names, thinks it's funny when he gets them wrong, terrible on Soccer Saturday when it comes to actually explaining what's happened.
Sherwood is worse. Comes across as an arrogant piece of shit that thinks he knows better than everyone else. Similar traits to Merson in just writing off any club or player that isn't English, and again thinks he's funny for it.