if Gamble is Evil Lancelot wouldn't Milli take the initiative? Imagine she assaults him because of Pinnacle Fluidation and he's just too uncomfortable to admit it.
That makes a bizarre possibility just that much stranger. Personally, regardless of how it goes, I had an image in my head of Gamble visiting Steele on his deathbed, with Chuckie staying by his side for appearances. He lights up a Cokie 100% tobacco cigarette, rants at him for a bit, then ends with "Sir, you've spent your Presidency screwing Ol' Caroline. But that's alright. Because I spent a similar amount of time screwing your wife." Steele has a massive final heart attack at the shock and dies. Chuckie cackles like a madman and thanks Gamble for handing him the Presidency. Then he probably either kills him or forces him out of the Chancellorship.