Railroad Baron

Morton: How does it feel sitting behind that desk, Frank?

Frank: Almost like holding a gun... only much more powerful.

—Once Upon a Time in the West

The owner/president/majority stockholder of a large and successful railroad. In the latter half of the 19th Century, owning a major railroad was a great way to get and stay rich. Not just because of fees for carrying passengers and freight, but land grants giving the railroads large easements on either side of the tracks, which could then be rented out or sold.

In fiction, the Railroad Baron will be dressed ostentatiously, with a gold pocket watch, fat cigars and other expensive accessories. They didn't call it the Gilded Age for nothing. Most of them will be middle-aged or older, and an expansive paunch is common. (One theory is that this stylized image was a mirror of their enormous and overbearing economic presence. Another theory is that it's just that most of them were rather fat, in a time when most people were lean from expensive or inadequate food.)

Because Aristocrats Are Evil, even "honorary" ones, Railroad Barons will usually be treated as an antagonist in stories. They'll have a Screw the Rules, I Have Money attitude, hire the Pinkerton Detective to deal with anyone who crosses them from Outlaw to union organizer, try to drive the Determined Homesteader off of his property so he can buy it up cheap, and arbitrarily change planned rail routes for maximum personal profit or to fulfill a vendetta. In short, an early type of Corrupt Corporate Executive.

Historically, they were expected to be generous with their money once they got it (and some of them actually were); but even the generous used these methods to acquire the money that they later gave away.

About the only time you'll see a Railroad Baron being treated neutrally is in stories about the Transcontinental Railroad being joined up.

Compare Cattle Baron.

Examples of Railroad Baron include:

Film

Sir Harry Percival in Cat Ballou (villain)
Morton in Once Upon a Time in the West (villain)
A Railroad Baron is seen briefly in The Wild Bunch and portrayed as worse (somehow) than the eponymous Bunch themselves.
McCabe in McCabe and Mrs. Miller is attacked by agents of a crooked railway baron's company after refusing to sell land to them.
Parodied quite humorously by Mel Brooks himself as the corrupt governor who stands to profit from directing the railroad through the town in "Blazing Saddles".
The Railroad Colonel (that's what the character is credited as) in the movie Rustlers' Rhapsody.

Literature

Tom Garner in The Power and the Glory (tragic hero)
A Sherlock Holmes novel by Larry Millett had one of the big (real-life) railroad barons in Minnesota as Holmes's ally and, possibly, client.
Harvey Cheyne's father in Captains Courageous averts most of the stereotype. He is treated as an often ruthless man but a more or less sympathetic one.
Dagny Taggart of Atlas Shrugged is pretty much the inverse of every stereotype of the Railroad Baron. Her railroad's founder, Nathaniel Taggart, is the idealized version of the stereotypical Railroad Baron; Ayn Rand probably modeled him on James J. Hill.
- Dagny's brother, James Taggart, almost fits this trope. However, due to his incompetence, Dagny (for the most part) runs the company, while he seeks political influence.
Harry King, in the Discworld novel Raising Steam, is a rare fictional Railroad Baron with a moral compass.

Tabletop Games

Most of the railway owners in the Deadlands roleplaying setting are pure evil (one of them uses a zombie workforce, another one uses evil witches as enforcers, the third one is a Mad Scientist, the fourth one is basically a Fu Manchu ripoff).
Every player in Rail Baron and Eurorails.

Video Games

Becoming one is the goal of Railroad Tycoon. Some campaigns even have you play as one of the Real Life barons.
Thomas Magruder, from the video game Gun. Big Bad, but is only using his railroads to find an enormous gold deposit that would make him incredibly wealthy and powerful.
The Fat Controller of Thomas the Tank Engine.

Real Life

James J. Hill
Cornelius "The Commodore" Vanderbilt (so called because he also owned a vast steamboat network as well). This is also why the sports teams of Vanderbilt University (which is named after him; he provided the then-huge million-dollar endowment) are called the "Commodores."
Jay Gould
Diamond Jim Fisk
Up in Canada, we have William Cornelius Van Horne, for whom there's a bit of a Broken Base. Some see him as a voice of reason and restraint in the otherwise muddled CPR project (after earlier barons caused a bribery scandal with the drunken, womanizing prime minister) and for actually finishing the damn Canadian Pacific Railway; to others he's a villain for the CPR's treatment of immigrant workers (they had to spend most of their income on food and lodging at the worksite, and ridiculously dangerous tasks).
J. Pierpont Morgan, though better remembered as a banker
E. H. Harriman
Real railroad barons did not specialize in railroads. The great businessmen of the nineteenth century had dynasties that could have a finger in whatever was the newest craze. One might for instance start as a whaler, shift to the China trade and get rich there. At that point they might reinvest their money into railroads or mines or stagecoaching or whatever. Or they might get into cattle.
- Sometimes the term, baron could be frightfully real. A large businessman owning the best organized investment in the area could have more firepower then any nearby pioneer settlement or Indian tribe. They seldom quite brought the West to the level of chaos that nobles in Medieval Europe did. But they could get involved in violence of various types depending on what business a local "baron" specialized in.