SpitfireIX
Philosopher
1995 Palo Verde, Arizona, derailmentProbably never. You can't crash a train the same way you can crash a plane. And sabotaging track isn't as easy as it sounds, especially if you don't want anyone to notice it before it causes a train crash. I'm not saying it can't happen, but a plane is always going to be a more attractive target than a train, because you can't just stop a plane in midair but you can just stop a train on the tracks.
1939 City of San Francisco derailment