Part of this is another breakdown in free markets. (Up front, 90% of what I know about shipping I probably learned from some of your pieces--so I'm no expert.)

A port should be free to offer its service to any shipping company that wants it. It basically loads and unloads a ship.

A trucking service should be free to pick up any load it wants, and if it doesn't like the service of the port, choose another.

Why isn't the above true? If it were true then shippers, ports and truckers would find a natural equilibrium.

My guess is that the port is the free-market obstacle. There is a limited supply of water access. Because it's a national interest, the government needs to regulate businesses who get use of these monopolistic franchises (for the area). The government does regulate like you say, between the ships and the ports. However, the problem is once a business is established at a port (or in any other area) it is hard to boot out. How does a competitor replace it? Theoretically it's possible, but not practical. What you end up with is government regulation not protecting a free markets but propping up incompetent management; often with more money, again, as you point out.

The government needs to do more to put ports up for bidding to other competitors. Maybe large truck companies HAHA!

People should care. We shouldn’t call ourselves a free market and not walk the walk.

I don't have an answer. As my wife sometimes says, "people suck"