After a problem with Tuddrussel messing with the controls, Time Squad travels to the year 46 BC to improve upon the flimsy city of Rome for Julius Caesar. But by the time the mission's complete, Tuddrussel doesn't want to leave! The Romans don't want him to leave ether. And Larry is forced by program to stay! It's up to Otto to train out-of-shape Caesar to beat Tuddrussel in combat to get everyone to snap out of their foolishness.

During a musical argument between Larry and Tuddrussel, Time Squad gets sent to the time of the great musician Ludwig van Beethoven. Now they have to get the message across to him, "No more pro wrestling!"

Larry refuses Tuddrussel's orders and accidentally downgrades himself. Tuddrussel asks for a burger, so Larry gives him burgers everywhere he goes.

Winston Churchill, the prime minister who leads England through World War II, is also leading everyone into being naked! Including Larry!

The Earl of Sandwich gives his new food the wrong name.

Time Squad goes to help Ben Franklin. But with what? And where can they find him? Those questons go through Tuddrussel and Larry's heads when they have to leave Otto behind because a bad cold he developed durring their previous mission to Antarctica. Now the two have to go alone into the mission--and the disaster they've always experienced before Otto came!

After Tuddrussel shows Otto a prision for "repeat offenders", Time Squad gets a mission--back to Black Beard!? It turns out he's gone back to his old wildlife tricks again, so Tuddrussel has to take him in. But they are sent to ancient Greece to convince Scocrates into being a pholosifer, not a fitness instructer, before they can even get back to the satellite. And once the missions complete, they notice that Black Beard has escaped!

Tuddrussel is trying to teach Otto a few things, like how to ride a bike, fishing, and catch, but Tuddrussel is not exactly the best person to. The History Instablility Alarm goes off, and the Squad goes back to help George Washington. Otto, of course, gets very excited. Washington and Otto strike up a friendship,... a very good friendship. So good, that Otto might want to stay with him and not go back to the satilite.

After Larry gets a birthday present from Otto (but not before he gets mad at Tuddrussel for denying he can even have one) the alarm blares for Paul Reverre. Yup, the guy who rides through Concord and Lexington warning the minute-men that the British are comming. Only one, eensy-weensy little tiny proplem: The guys afraid of horses! In need of a psychiatrist, our heroes have to transport to Austria to get help from--you guessed it--Sigmund Freud.