James - Unless you are pushing against the point of the pin (perhaps your retainer is clocked so the flat of the pin doesn't go straight through the slot in the retainer?), when you compress the spring and retainer the pin should go through the slot on the retainer, with limited effort to hold the pin in place while pressing down on the spring and retainer clips.
Below is a typical brake diagram (a picture I snapped from a 1949 Delco Brakes Service Manual) that shows the relationship of the shoe retaining pins/springs/clips. The clips are designed with a straight slot for the pin to slide over the pin point during compression, then the clip gets rotated 90 degrees to allow the flats of the pin point to settle into a groove that prevents the clip from coming off the pin.
~ Dan 1951 Chevy 3 window 3100 Follow this story in the DITY Gallery "My Grandpa Carl's Truck and How it Became Mine" 1966 Chevelle (Wife's Hot Rod) | 2013 Chevy Silverado (Current daily driver) US Army MSG Retired (1977-1998) | Com Fac Maint Lead Tech Retired (1998-2021)
