MrWidmore - This would be cool. I do believe that Jacob knew that MM was up to something, from the start, with Locke and using Ben as his counter strategy would be brilliant. I also think MM was so tied up in his moves that he didn't realize that Jacob had caught on to him. MM even says "you don't know what I went through..."in a rather smirk way.
Analogous to a chess game (which we see an awful lot) - when you think you have a no-lose strategy you can get so focused on your moves that you miss the fact that your opponent has figured out your plan and has developed a strong counter plan. You ignore their moves and strategy and then BAM, next thing you know you are on the defensive or worse, you LOSE.
And, this idea is out-of-the-box enough to be a good LOST twist. If nothing else, we are continually thrown twists to which I think almost all of say "what the $%^& just happened????!!!.