Hey AhavahOlam, it's a comic strip, not a political statement, not a precis nouveau. Please make an attempt to remove the stick that has been firmly implanted in your @$$ during your college years.
No. He's just lazy and wants to make more money out of it. You'll find that Scott almost never tries to work hidden meanings into these - just enjoy it for what it is (ie. funny).
Wally is a version of the neo-liberal yuppies who have not worked for "the man" so they idolize the said power so they can continue to live on expensive coffees and their parents wealth and speak about the Utopian ideal of the fashionably propagandized communist/socialist movement. ("Worthless" - pun, and "over paid" = the assumed power of wealth.)
The last strip is great, because Wally realizes(superficially) that the boss is grumpy because of the reality of Wally's realization, kind of like a modern telling of the sword of Damascus, having over the leaders head (PHB), thus causing his less than amorous mood.