Trailer jack and trailer neck toolbox clearance issues

[Hay Dude]

Rotate it 90 degrees so it is a front winder.

Bruce

Then it hits batter box lol

 

[Hay Dude]

It could be awkward to wind a front winder if there isn't much space to operate the crank handle between the tailgate and the jack.

Rather than rely on a cordless drill battery to always be charged, I'd think about keeping a ratchet wrench with the right socket in the toolbox.

I’m covered for both. I keep a 2 drills on the truck and a DeWalt DC battery charger plugged in with a battery always on charge.