Taleb is a Trump like clown. Just because both have the capacity to point of hypocrisy in the system, don't let that misguide you into believing they are qualified to talk about solutions. There is no comparison to Pinker.
Taleb doesn't take himself seriously, Pinker takes himself far too seriously. Taleb is entertaining, Pinker draws out his ideas to the point of tedium. Taleb is a skeptical empiricist, Pinker likes to get lost in theory.
Pinker certainly has Taleb lapped in terms of old guard intellectual credentials. Whether that is a good thing is debatable.
I don't think Trump would pack those venues so full of people if he wasn't somehow in tune with what a whole lot of people are thinking. He is easy to dismiss. He is not a politician. He is not pre-packaged or polished. He is not particularly well educated. But he's right--the US is not living up to its ideals. We can even run a clean election.
America ended in 2008. We've been living off of a corpse ever since. At some point everyone is going to know it.
To reiterate: just because he recognizes the malaise, doesn't mean he has a cure. I had a political scientist who described Communism as having diagnosed the disease (class struggle), but having been unable to come up with a reasonable cure.
Pinker certainly has Taleb lapped in terms of old guard intellectual credentials. Whether that is a good thing is debatable.