The first thing that I would look at is the adjustment and the linkage. Start easy. If one pedal is sloppy and the other is tight, then you're onto something. Also, making sure that the linkage is good all of the way is a big step.
IH Farmall 656 gas/ IH 240 Utility/ 2, Super C Farmalls/ 2, Farmall A's/ Farmall BN/McCormick-Deering OS-6/McCormick-Deering O-4/ '36 Farmall F-12/ 480 Case hoe. '65 Ford 2000 3 cyl., 4 spd. w/3 spd Aux. Trans
Here is an exploded view of a 5105 from JD parts page. Just wondering if that snap ring popped off the end of the brake cam..?? I'm guessing that shaft is splined. Everything else looks like basic linkages externally.
Linkage looks fine, its weird the side that locks up has good firm pedal, the side that dont work has no pedal. Like brakes on a care when they need bleading. I worked the linkage by hand under the tractor and that brake still would not work. Looks like ill be tearing into it all.