* In a world of increasing automation and outsourcing, there is still demand for the ruthless cost cutter, head hunter, negotiator. And that work can't be done by just anyone, so the small percentage that do it well are paid well for it.
* There may be a possibility that ruthlessness enriches families when euthanasia becomes more accepted. The heirs get a richer inheritance if they turn off Mom's life support sooner or talk her into suicide at 70 versus drawing down her savings for five more years; it is a modern variation of the "powders of inheritance" of the Middle Ages that would literally make the ruthless heirs much better off.
* I've been reading "So You've Been Publicly Shamed". The thorough, perhaps insanely dedicated investigators who found some of the plagiarists and liars were well rewarded with scoops and better paying journalism jobs. The ruthless went forward with reports and did well. Major incentive to ruthlessness when journalism itself is in decline.
* To what degree is click bait journalism and intense smearing of one's political rivals a career path for the ruthless? Whether rumors Obama was not born in the US or the AP publishing the VP's wife's phone number knowing she'll get harassed, the abominable jokes about Trump's ten year old son or idiotic insults about Michelle Obama's figure ... the internet is making the ruthless trolls who play well to their audience rich, as well as rewards journalists who dispense with facts to fit the stories that play to the audience's biases or get them paid well by benefactors/political parties.
* When political correctness couches censorship in courtesy and social protocol, only the loudmouth jerks, dedicated contrarians speaking from principle regardless of personal cost and ruthless critics who wield "I'm offended" like a blade remain speaking in the public square. And the "I'm offended" get extra moral weight from liberals who give extra attention and support to the first person to claim victim status or whichever side is lower on the victimhood hierarchy. Free speech, the debate on ideas that prevents drift to untenable extremes and exchange of thoughts that lead to innovation all suffer as a result.