“It’s cheaper to send a kid to Yale than to send a kid to jail. Penn State is cheaper than the State pen,” said U.S. President George H. W. Bush while campaigning for re-election in 1992. The saying means that young people are all too often sent to prison when it would be cheaper to send them to college. Society pays a large cost for this failure.
 
“It costs taxpayers more money to send a person to jail than it would cost to go to Yale University” was cited in 1988. “A full scholarship to jail costs $6,000 a year more than a full scholarship to Yale,” American civil rights activist and Baptist minister Jesse Jackson wrote in 1991. Jackson is believed to have coined the saying in the 1980s.
 
   
Wikipedia: Jesse Jackson
Jesse Louis Jackson, Sr. (born Jesse Louis Burns; October 8, 1941) is an American civil rights activist and Baptist minister. He was a candidate for the Democratic presidential nomination in 1984 and 1988 and served as a shadow U.S. Senator for the District of Columbia from 1991 to 1997. He is the founder of the organizations that merged to form Rainbow/PUSH.
 
Google News Archive
29 February 1988, The News-Journal (Daytona Beach, FL), “Ministry group hopes to fight jail overcrowding with program” by Velma Howard, pg. 4B, col. 2:
“It costs taxpayers more money to send a person to jail than it would cost to go to Yale University,” John said.
     
11 August 1991, Evansville (IN) Courier, “Connecticut rally focuses on shame of decaying cities” by Jesse Jackson (Los Angeles Times), pg. G3, col. 5:
A full scholarship to jail costs $6,000 a year more than a full scholarship to Yale.
 
Google News Archive
7 September 1992, Sarasota (FL) Herald-Tribune, “Bush Goes Blue Collar” (Los Angeles Times), pg. 5A, col. 3:
And (President—ed.) Bush, whose speeches usually sound an unrelenting call for law and order, appropriated the rhetoric of Jesse Jackson as he reminded the crowd that “it’s cheaper to send a kid to Yale than to send a kid to jail.”
   
Google Books
Public Papers of the Presidents of the United States:
George Bush
Washington, DC: Federal Register Division, National Archives and Records Service, General Services Administration: For sale by the Supt. of Docs., U.S. G.P.O.
1992
Pg. 1491:
It’s cheaper to send a kid to Yale than to send a kid to jail. Penn State is cheaper than the State pen.
 
Google Books
September 1994, Black Enterprise, “United Negro College Fund” by Mark Lowery, pg. 137, col. 3:
It is a slight variation of Rev. Jesse Jackson’s often used phrase, “We can send them [our children] to Yale, or we can send them to jail” — substituting the names of Philander Smith, Talladega, LeMoyne-Owen and Wilberforce for Yale.
     
Google Books
Violence as Seen through a Prism of Color
Edited by Letha A. See
New York, NY: Haworth Social Work Practice Press
2001
Pg. 163:
Despite Jesse Jackson’s admonition that it is more expensive to send a youth to jail than to Yale, and to the state pen than to Penn State, incarceration has become the government’s option of choice.
   
Google Books 
From the Palace to the Prison
By Sherman D. Manning
New York, NY: A&M Publishing (HarperCOllins)
2005
Pg. 83:
We know it costs more money to send a man to jail than it does to send him to Yale.
 
Google Books
Why School Reform Is Failing and What We Need to Do about It:
10 Lessons from the Trenches
By Jerry Wartgow
Lanham, MD: Rowman & Littlefield Education
2008
Pg. 65:
It is approaching the point where it will be cheaper to send a person to “Yale than to jail” or to “Penn State than the State Pen.”
 
Twitter
DoSomething.org
‏@dosomething
“You can send two kids to YALE for the same price as one kid to JAIL.” - @VanJones68
4:29 PM - 29 Apr 2014
 
FOX4 KBTV (Beaumont, TX)
‘Creative Corrections’ working to break cycle of generational crime
Updated: Tuesday, May 19 2015, 10:23 PM CDT
BEAUMONT-by Kara Dixon
(...)
“You know there’s that old saying that it’s cheaper to send a kid to Yale than it is to jail and I don’t think our communities and country understand that,” he said.