Imo, IF they're working "together" (meaning Trump is sufficiently aware of the game, and intends to play it down to the conclusion the Clintons seek) then I'd bet we'll be able to detect it.
they both lose value in a debate. Right now, trump's masses love him because he controls the conversation, repeating anti-mex catch phrases.
Once he has to fumble his way thru lessons we've learned from WWII or three specific ways he will maintain trade while initiating sanctions upon RUS or CHI, his simple talk just ain't gonna cut it anymore.
"Sir, please elaborate..."
"I'm tired of the media and their tricks..."
"Sir, what lessons did we learn"
"the world learned you can't mess with us..."
"Sir, what about china"
"China knows not to mess with me..."
At some point, people will realize, um, he doesn't actually know any specifics or have a grasp on history, does he? Reminds me of Tim Tebow... great leader, amazing willpower, terrific gifts... but just didn't have the acumen or manning-esque mental horsepower to read defenses.