It's actually insane how useless Chester is! While watching these early entries in the show you can't help but to think why in the world does Matt keep him around? Most of the time he's literally just there to complain and make obvious comments, wow. A sidekick is at least supposed to come in handy and provide some kind of aid to where the lead is lacking. Matt has to do ALL the work.
For instance, in this episode when they were trying to send the telegraph off to get a description of Lou Shippen. A clever number 2 would've been able to think quick on their feet and do something like pretend to know how to read Morse code or whatever to get the guy to cooperate. Chester just goes "uh derrr what about the telegraph mR. DiLloN?" Come on!!!! Thank god Matt does something similar later on.
Also, this Lou Shippen is a back shooter as we learn in the opening scene but the whole time in Elkader instead of attempting to watch Matt's back or blind spots he just stares idiotically at Matt or where/whoever he's looking at. When they were at the bar in Elkader Matt asks did he catch something, a signal I believe to notice which person is Lou... "uh derr no mR. DiLloN I don't know where to look unless you tell me."
SOMEONE PLEASE GIVE THIS MAN A CLUE!
And I get it, I see how Chester can be a lovable character. He does grow on you sometimes with his simple minded comments and banter with the main cast, but for me it's frustrating because for the most part he seems to be no help whatsoever to Matt when investigating and pursuing outlaws.