Should I pay ?

I'm confused.

Are you an owner operator that tried to lease on to someone, or were you trying to do a lease purchase from someone? Or were you a driver that worked for someone that somehow you were paying these expenses?

And what is the loan about? Why are they loaning you money?

You damaged his trailer? Aside from whatever else you agreed to, if you damaged someone"s trailer you have to pay for it.

 

So I'm also confused.

I am going to repeat Dino's questions - Are you an owner operator that tried to lease on to someone, or were you trying to do a lease purchase from someone? Or were you a driver that worked for someone that somehow you were paying these expenses?

It looks like you were an employee.

 

I have an opinion but think I'll kick back and hear "the rest of the story"

 

Well so you're not a Owner op your just a driver leasing a truck. Own ur mistake like a man and move on.

 

So,
1. you agreed to work for him in such a way, that you leased the truck from him for $500 per week and the trailer for $250 per week.
2. the guy - your lessor - gave you $2000 loan to get going - you paid that back in full
3. you damaged the trailer - the costs of of the damage were $1500
4. 2 times you drove 1500 miles and you did not receive the money because the money went to pay that $500+$250+insurance+gas.
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From the moral standpoint, you should pay him for the damages because nowhere did I see, in your description, any moral damage he had done to you.

For the 2 times, when you drove 1500 miles, you think you were not paid but you were paid and the money were subtracted from your settlement check, and applied towards your liabilities.

His giving you the loan, that you paid back has nothing to do with your liability to pay him for the damage. Neither, your helping him out to pay ahead for "his" lease - which I assume is "your" lease of $500+$250 - has anything to do with it, unless your paying ahead was not reconciled yet, meaning if he still owes you money on that.

In other words, the only scenario, when you would not want to pay for the damage, would be when he owed you money for the work you had done for him. If he already paid you every dollar for every trip you had done for him, then you owe him for the damage.

 

IMO, if you were working " for him" then he's your employer. Let him pay. He can write it off as a business expense. Just ignore his phone calls, letters, texts etc because when he "loaned" you the two grand it was because he assessed you as someone he could take advantage of in his business dealings and you took the bait. Avoid him, he might have some other crafty trick up his sleeve that he wants to reel you in with.

If you worked at McDonald's and broke the milkshake machine, would they make you pay for it? Cops, mailmen damage their vehicles. Nobody makes them pay for it.

 

OK here is the thing, you as an employee don't pay for anything - PERIOD.

He owes you the money that he charged you, he owes the taxes on the money he is supposed to pay you and your wages.

He can't expect you to pay for damages for the trailer that he owns, it isn't legal.

I would start with contacting the state labor board and asking how to file a complaint, then to the state tax office to file a complaint and then the IRS to ask how you can file your taxes without the withholding he legally was responsible for.

It doesn't matter if he claims you are an independent contractor or not, if there is no contract (doubt there is) and if he told you that you have to pick up any load without it being in the contract as to what you are supposed to do, then you are an employee - PERIOD - and you are to be paid.

One other thing is to document things very carefully and accurately, like a time line and what you paid and didn't pay and the conversations with him.