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What to put in a trailer toolbox?

Id fill mine with tp never leave home without it .
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though the more I think back to boy scouts the more it reminds me of the Hitler youth programs not sure why
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It's a 14' utility trailer.

What does it haul? That's what you need to base it off.

If I was hauling a sxs, I'd toss a Milwaukee ratchet set in, some 2k ratchet straps, some 2k zip straps, some axle straps, and I'm done.

For a mower or sxs even if it's dead you can alternate decent quality ratchet straps back and forth to pull a dead one up without carrying a come-a-long. Unless you're using it regularly the come-a-long sucks ass. Mine has been hanging gathering dust for years.

My 25' goose tilt deck has piles of 3k, 6k, and 9k ratchet straps, 5/16 and 3/8 transport chain, and 8 binders. I've pulled a dead truck onto it just alternating binders on a chain. Slow as hell but it got the job done the 1 time I needed to in 10 years.
The goose hauls skid steers, mini ex's and trenchers; along with random pallets and generators.

Whereas my enclosed just has straps for dirt bikes and snowmobiles. Doesn't need anything else.



I toss a floor jack and a few 2x's in the bed of the truck whenever I hook onto a trailer. M18 impact with a 12.0 battery and impact sockets live in the truck 100% of the time.
 
If you're putting anything of value in it, a heavy duty hasp and a quality lock, rather than the POS wafer lock it probably came with that anyone with youtube can open in 15 seconds.