Wasn't that the one which they accidentally counted their costs twice so that what they thought was a loss making operation actually turned out to be making a small profit? That would certainly point to some rather large failures of management. As for their Lines West I know the popular history has it as the best line to the North West but I can remember reading a study and an article that question how superior, if at all, they were to the alternative lines. I'll see if I can find the links again.

Edit: I see that it was. It was also the railroad whose chairman offered to give it away free of charge to the Burlington Northern except for assumption of its debts. The only reason it didn't go through was one of the Chicago-Milwaukee Corporation–the holding company of the railroad–board objecting as they thought the large land holdings the Milwaukee Land Company owned was worth $50 million which scuppered the deal. Later on the land, which was mostly used for timber, was sold for $125 million. It really does seem to have been a comedy of errors.
 
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Would probably require a merger. My vote goes to C&NW.

Too many duplicated routes in the Midwest, and Milwaukee Road pulled their offer on that to C&NW in the late '60s when they saw the C&NW was in far worse shape than they themselves were in.

Rock Island makes a little more sense, but Illinois Central would have been a better fit, getting some North/South connection to the upper Midwest
 
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