True outsider vs symbiotic relationship

This came up in discussion that started with Ivo Stourton and Russell Brand.  Stourton’s described in The Mail Online as “The 29-year-old son of journalist and broadcaster Edward. Gained a double First in English after attending Corpus Christi College, Cambridge. Has since signed a two-book deal with Random House and is currently working as a lawyer with Slaughter and May.”  In other words, the epitome of an establishment insider – arguably just like Ian Hislop.  Is someone in a symbiotic relationship with the establishment able to confront or hold it to account in the same way as a true outsider?