Tuddrussel is showing Otto some outrageous souvenirs from the past when they get a mission to the time of the Trojan War, where the Greeks sneaked a giant, wooden horse into Troy's kingdom, filling it with solders to attack when the horse is opened, to win the war. Instead, they're filling it with candy for the king of Troy's birthday!

As an aftermath to Larry showing Otto their awful bloopers from their missions before he came, Time Squad is now trying to get the Wright brothers to making the first airplane instead of working on their incredibly dull stunt show, and Otto is scared when Tuddrussel wants to do things his way.

Buffalo Bill was the one to start the first mail service called the pony express. But when Time Squad finds him, he has some crazy ideas on his mind other than postal service. And I mean crazy. Time Squad must get him on his horse, delivering mail.