Hauling a Harley with my 1st gen Tacoma

I didn’t try it diagonally I just put it straight in. That’s how I normally load my bikes, straight in with a bed extender. But the Harley was actually too long I couldn’t fit the bed extender on the tailgate either... but I don’t think it was the driving with the tire on the tailgate that tweaked the tailgate, it was the loading/unloading with the full weight of the bike (about 700lbs) that bent it

 

It is still too long to close the tailgate. It makes it a lot harder to tie down like that also. Your best bet is a sheet of plywood under, straight up the middle and tie it standing up. Ive actually seen 2 bikes tied on the kickstand break the kickstand off the frame. You also might build a wheel chock out of 2x4 to keep the front wheel straight, it will want to turn otherwise