Just to add to this, I've driven for UPS and Airborne Express. I've had accidents and damaged peoples yards more then once. It happens all the time. The company deals with it and every time it happened, I notified my supervisor and rarely ever heard about it again. It's what the company has insurance for. A few times the homeowner claimed more damage then was done, and/or wanted an amount that was ridiculous. In those case, I was asked again what happened.
In my situations, the driveways were steep and slippery. The vehicle slid off of their driveways and caused the damage.
Later, when I became a Union Steward, I was involved in quite a few accidents and disputes with drivers. The only times the driver would get into trouble was when he didn't report it, or lied about it. With the power of the union behind me, we worked through it, but in every case, if the driver would have never been brought in for disapline if he had just reported it and let management handle it.
If the drivers job is on the line, it's more then likely due to doing this on a regular basis, not reporting it like he is supposed to, or he's not very good at his job and they are looking for an excuse to get rid of him. Even if you go through the process of having him fix it or pay you to do it yourself, he might lose his job anyway. Holiday drivers are temporary and only hired for the season. Most new hires don't work out and are gone in a few months. If he's an experienced driver with a good driving record and work history, his job wouldn't be in jeopardy for this.
Eddie