Company taking a $250 deposit out of my check for 4 weeks.

Since I started driving in the 60s I've worked for all kinds of companies. Some of them were straight arrow and honest to a fault. Others were so crooked that if they told me a log was made out of wood I'd want a core sample just to be sure.
But none of them, good companies or bad, ever required a "damage deposit" or an escrow of any kind.
I trust the drivers I have working for me. I don't require a damage deposit from them. I have good insurance and, failing that, I have a darn good shop. We haul mostly off road these days and a few dings and dents go with the territory.
Also, I've found that when a driver screws something up he's unlikely to make the same mistake again any time soon.

 

Find a job with a reputable company asap!

 

It's not just the Chicagoland companies doing this. At one time, Carol Fulmer required you to have an escrow deducted from your check, not sure if they still do or not. And they've been around a while, so it's not just the fly-by-night companies.

Either way, I would take my stuff and leave, even if it was on the bus.

 

I too ran the gamut with companies, but never once was asked for a deposit of any kind. Didn't have to, the boss knew a responsible driver when they saw one. I ruined a set of duals on a trailer on my last day at a job once, and offered to pay, but the boss was cool. Thing is, today, for many, there is no consequence to their actions. They simply quit leaving the company with yet another expense they can't cover. You obviously screen your drivers pretty well, but some companies, I bet you never even meet the boss. As far as a "one and done" screw up, even that one infraction can be costly, and companies have no choice but to charge a deposit. Seasoned drivers will tell them to cram it with walnuts, but newer drivers may not know the difference, and as shown, will sign anything to just get a job.

 

I think you should look 4 different employment and gain more information on what a w2 employee is because it sounds like you are a 1099 contractor now.