I have yet to see a decent operating manager who did not come out of the ranks.
Now if we're talking about the guys in legal, finance, sales, logistics, etc, well, they are not really rails. They might as well be working for any mega corporation as their skillsets are not specific to the railroad industry. The guy above could work in sales or shipping for Wonderbread and get just as much job satisfaction at seeing a kid eating a peanut butter sandwich as he does at the sight of a passing train. His contribution to the end result is just as relevent.
If management is your long term goal, I'd say get that degree first. It will open more doors for you, especially later in life.