First, I think this is an interesting topic to debate and discuss. I'm not sure whether Roberts is a traitor, a genius or something in between. It is not "my approach" and I don't buy everything the author has written at all.
My primary point is that if SCOTUS had declared 0bamacare unconstitutional in June, 2012, everything that was wrong with 0bamacare would have been blamed on this SCOTUS decision rather than the bad law, the Left would have launched a scorched earth attack on the rule of law and SCOTUS that would have made Bush v Gore look tame, ending in a scenario where we truly "could have lost by winning".
I don't think you'd find many military historians who think losing to win is a viable scenario, and you know Patton's motto, "Don't pay for the same real estate twice."