Yes, it's a matter of when - I think I saw a stat that the average Engineer hits slightly more than 3 cars over time
My friend Joe told me this story - he was riding Amtrak sometime around 1980 (If I think hard, I could probably pin it closer), and for a rare once, they were about 2 hours out of Chicago, and ON TIME. Suddenly, he felt the brakes engage, then go into emergency - and the train stopped
They had hit a car, and rolled it up on the plow - the good news is no one was in the car - and they did allow folks out of the train to stretch their legs. Joe summed up the dammage to the train - they had to replace a brake hose, and slap some black paint on the plow - the car, on the other hand, was a small ball that had to be pried out from under the coupler.
The arrived the usual 6 hours late