Accountability for accident while driving team

Hey everyone, I have a slight concern and am hoping to be at least pointed in the right direction.

In theory: Jane (10 years driving, mostly oil patch tanker) gets sent on a run she has never been on (say, first time in the Rockies in a semi, in winter) and Joe (he says 20+ years driving, been everywhere, done everything, knows it all) offers to tag along in case there are problems, and to help with the driving if needed because the delivery has a strict appointment time.

Joe offers to take the first couple of hours to give Jane a chance to catch some rest before the mountains. Before he is even out of the yard, he runs the side of the trailer along another truck. Luckily, only a couple of scratches to both vehicles and off they go.

Joe does not want to start a log book because he is "only helping out and doing a favor", so everything gets logged under Jane (somewhat creatively, but it looks good on paper).

Day 2, after spending more time lost than not, because Joe "always knows exactly where they are, and just turn here", Joe takes over at the end of the day and offers to go get the trailer washed out while Jane sleeps. More lost time, truck washes that don't exist but were "there just last week!" and one no exit road that Jane mentioned didn't look like it went anywhere, but Joe "couldn't see a sign that says so", there is a tow truck needing called to pull the truck and trailer off of the extremely wet and soggy grass that Joe got the truck sunk in. Joe gets frustrated and hides in the bunk to leave Jane to authorize, deal with, and eventually pay for, the tow truck.

Day 3, Jane parks on the side of the road at the truck dealer and gets out to drop the trailer so she can hopefully have a tech check the door seal that lets in hurricane force winds at -30. Joe yells at her to just "drive the ##### truck right into the parking lot, don't bother dropping the trailer, that's stupid". So, since he said he was "just in there last week the exact same way", she drives straight in. It's a bit tight, and the trailer is hanging into the back road, but come time to get out it should be OK. The tech comes out, looks at the door, says he can't do anything, and asks Jane if she'll be able to back out as it looks good pretty tight. Jane is fed up and tells Joe he can deal with getting the truck out since he's the one who said to put it there in the first place. Joe promptly backs along a logging trailer and tears a 4 foot hole in the side of the van trailer. Eventually he gets it out, jumps out of the truck, slams the door and stomps around saying he's not driving anymore this trip and to take him home, load be ######.

Joe has now informed Jane that he is telling the boss it was all her and that she can't prove otherwise because he doesn't have a log book so isn't technically there. After much yelling, swearing and a slight bit of police involvement, Joe agrees to fess up to the boss. Next day, Joe gets fired (surprise) and goes on a rampage about how Jane is responsible for half of the tow truck bill and trailer repairs, since she was awake when they happened, and that he's putting in for half of the miles because he "don't work for #### free".

I could care less about the miles right now, but is there any way Jane is actually responsible for paying for the damages etc???

Thanks!!