Orton as a heel came out on top. Punk with SES losses all his matches and feuds with guys like Rey, Big Show, and so on. He loses his matches that rookies were winning as part of Nexus against Orton by himself when Randy couldn't overcome the odds without the help of other vets. It is just a flaw in his character's booking. He is the guy who goes into the big matches as a heel with the odds in his favor and falls on his face, whereas Orton as a heel, Edge, HHH, Dave in Evolution came out ahead to lead to a bigger payoff. The only guy who I can really point to that has done the same in recent times is Jericho, who like Punk doesn't lose his loyal heat or fanfare, but also will never be the poster boy of the main brand in a long term, transitional yeah, but never long term fashion because he just isn't in that mold.
Legend Killer Orton, Age of Orton, Legacy Orton, whatever came out on top as a heel at a fair ratio, whereas Punk isn't that guy besides sending Jeff off from the b brand and company