“A man who has never gone to school may steal from a freight car; but if he has a university education, he may steal the whole railroad” is credited to Theodore Roosevelt (1858-1919). There is no record that he ever said it, though it is possible; forms of the saying were used in the 1890s, before Roosevelt became president.
 
This was printed in several newspapers in 1894: “Steal a ride and you are a ‘hobo,’ liable to be shot. Steal a whole railroad and you are a financier, eligible to the United States Senate.”
 
Reverend Dr. Wilber F. Crafts, superintendent of the Reform Bureau at Washington, said this in 1899 (and in many other years): “An ignorant thief may rob a freight car; an educated thief will steal the whole railroad.”
 
The saying (according to Dr. Crafts) illustrates that, without morals, education will only further a greater crime. The saying also shows that small, common criminals (“blue collar crime”) are often immediately and severely punished, while greater criminals (“white collar crime”) are often rewarded. A somewhat similar saying is: “The best way to rob a bank is to own one.”
   
     

Wikiquote: Theodore Roosevelt
Theodore Roosevelt, Jr. (1858-10-27 – 1919-01-06), also known as T.R. or Teddy, was the 26th President of the United States (1901–1909).
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A man who has never gone to school may steal from a freight car; but if he has a university education, he may steal the whole railroad.
. As quoted in Art of Communicating Ideas (1952) by William Joseph Grace, p. 389
   
Chronicling America
6 June 1894, Morning Call (San Francisco, CA), pg. 6, col. 5:
Steal a ride and you are a “hobo,” liable to be shot. Steal a whole railroad and you are a financier, eligible to the United States Senate.—Philadelphia Item.
 
Chronicling America
9 November 1894, Salt Lake Herald (Salt Lake City, UT), pg. 3, col. 7:
We all have heard in our lives of kleptomania; but I do not think that any one ever really believed in it. We know vaguely that a man who steals whole railroads and dies a millionaire is a great financier, and we also know that a man who steals a loaf of bread to save his family from starvation is a thief and goes to jail, but it is hard to realize that there are people who steal trifles simply from a species of insanity.
 
Google Books
31 December 1898, The Literary Digest, pg. 769, col. 2:
A TEN-YEAR-OLD lad in Indianapolis who was arrested for picking up coal along the side of railroad tracks is now in jail. If the boy had known enough to steal the whole railroad he would be heralded as a Napoleon of finance.—The News, Chicago.
 
28 March 1899, Baltimore (MD) Sun, pg. 10:
REV. DR. CRAFTS ON THIEVES
“An Ignorant One May Rob A Car;
An Educated One Will Steal
The Whole Railroad.”
In an address last night before the executive committee of the Christian Endeavor Society, at the Central Hall of the Young Men’s Christian Association, Rev. Dr. Wilbur F. Crafts, of Washington, characterized the prosperous nations of the earth as the Sabbath-keeping nations.
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Passing from the discussion of the dying nations to the needs of the living, Dr. Crafts said that the strength of a nation is in its institutions. He said:
 
“We need as a nation to learn lessons of Christian morality. It is not worth while to educate a man’s wits unless you educate his conscience also. An ignorant thief may rob a freight car; an educated thief will steal the whole railroad.”
 
Google Books
Making a life
By Cortland Myers
New York, NY: Fleming H. Revell
1900
Pg. 237:
“An ignorant thief robs a freight-car. An educated thief steals the whole railroad.”
   
20 October 1902, Worcester (MA) Daily Spy, pg. 4:
This series of deceased empires teach also that our culture must not ignore morals. better a man be not educated, if his conscience is not to be developed with his wits, lest he be the more skillful criminal. “An ignorant thief may rob a freight car; but an educated thief will steal the whole railroad.”
(Speech by Rev. Dr. Wilbur F. Crafts, superintendent of the Reform Bureau at Washington—ed.)
   
Google Books
Practical Christian Sociology;
A series of lectures at Princeton Theological Seminary and Marietta College on moral reforms and social problems, with 20th-century statistics
Revised 4th Edition
By Wilbur F. Crafts
New York, NY: Funk & Wagnalls Co.
1907
Pg. 280:
The illiterate robs a freight car; the educated thief steals the whole railroad.
 
Google Books
Bulletin of State Institutions [under the Board of Control]
By Iowa. Board of Control of State Institutions
Volume 11
1909
Pg. 5:
If a man steal a ride on a railroad, he is called a “hobo;” If he steal the whole railroad his name is emblazoned in history as a financier.
   
Google Books
September 1912, The Child, vol. 1, np. 7, pg. 36, col. 1:
Washington Gladden has said—with how much truth I leave it to you to judge—that if a man steals a ham from a freight car, he goes to jail; while if he steals the whole railroad, he goes to the United States senate.
 
Google Books
Bible in schools plans of many lands; documents gathered and compiled
Edited by Wilbur F. Crafts
Washington, DC: Illustrated Bible selections commission
1914
Pg. 125, col. 2:
As one has wittily and wisely said, “YOUR IGNORANT THIEF MAY ROB A FREIGHT CAR; YOUR EDUCATED THIEF WILL STEAL THE WHOLE RAILROAD.”
 
Google News Archive
25 June 1929, Daily Times (Beaver, PA), “America Faces Moral Bankruptcy,” pg. 6, col. 2:
“An uneducated thief,” said Dr. Maier, “will steal a ride on a railroad train. An educated thief will steal the whole railroad system.”
(Dr. Walter R. Maier, professor in Concordia Theological Seminary, of St. Louis—ed.)
 
10 September 1950, New York (NY) Times, “Freshman Primer,” magazine, pg. 168:
“A man who has never gone to school may steal from a freight car; but if he has a university education, he may steal the whole railroad.”
—Theodore Roosevelt.
 
4 February 1963, Trenton (NJ) Evening Times, pg. 36:
It was President Theodore Roosevelt who observed, “A man who has never gone to school may steal from a freight car; but if he has a university education, he may steal the whole railroad.”