fartheststar: My immediate impression on #1 was George Washington chopping down a cherry tree. I have no idea if any games have that historical type theme (although one of the Assassins Creed titles popped into my head I don't know if they participate in bundles).
IAmSinistar: My immediate impression as well, that it represented George and the cherry tree story. I can't think of any game that might represent at the moment, unless there is an American Revolution title that fits the bill. Also, the apocryphal cherry tree incident is the basis for him supposedly saying "I cannot tell a lie", so perhaps that is a clue. Any games out about lying?
Only other title I can think of that represents that pic is
Battle for Presidency.
Seems kinda unlikely, but who knows.
IAmSinistar: By the way, I see no reason why Redshirt wouldn't be bundled. It certainly wouldn't be the quickest retail-to-bundle ever. Folks have mentioned Ethan Meteor Hunter already, and Ittle Dew showed up in a bundle in surprisingly short order as I recall.
Shufflepuck Cantina Deluxe was released in December, and there's an extremely high chance that's in the bundle.. so I would have to agree.