Barry lives by the axiom of "leading from behind", a double entendre that conveniently allows him to think he doesn't have to be particularly proactive and ahead-of-the-curve to accomplish what's needed: Social Security inconsistencies, Selective Service Application, LFBC, unpleasant dearth of photographs from the past that would accompany a savory, electable life, gay lovers in Chicago that have turned inconvenient, State legislature papers, etc.
Frankly, what he counts on is his handler's clean up crew to wash the bed linens and do cover-ups for him.
In another slant on things, he likes the phrase because he considers himself in charge sexually, so much that he's incorporated these things into his very signature:
hiding with a wink and a smile... 