SOURCE: REPLACINGTHE REAR TIRE ON A HARLEY DAVIDSON 2008 HERITAGE SOFTAIL
Down and dirty way - take it to the dealer and have them install a new tire....
The hard way: place bike on bike jack and remove rear wheel by removing the axle nut and drifting the axle out of the wheel. Derail the belt/chain and drop the wheel out of the brake caliper. Remove valve stem to deflate the tire. Get a set of tire spoons and a 12 pack of COLD brew cause working with tire spoons is no FUN! Pry the bead loose with one spoon and the work your way around the wheel prying the tire beed to the outside of the wheel. Repeat this process for the back side of the tire (in the same direction as the first side so the tire will come off the wheel. Reverse and repeat to install new tire.
By now you will be loading your wheel into the truck and heading to the HD shop. It just really isn't worth the hastle to save the $25 or so to have this job done.
Align wheel with new tire on it with the brake caliper so that you have one shoe on each side of the rotor (you may have to actually remove the caliper if your pads are thick. Install your belt drive/chain drive and then lift the wheel to insert the axle through the swing arm, the chain tensioner and wheel. Reverse
on the other side. Place axle nut on axle and torque to about 80lbs.
Good to go.
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