The “Buffalo nickel” or “Indian Head nickel” is a U.S. five-cent piece with a buffalo design on one side and an Indian head design on the other; the coin was minted from 1913 to 1938. A person who is tight with money is someone who “squeezes a Buffalo nickel so tight the Indian cries.”
 
“The father was the kind of man who squeezes a nickel so hard the Indian cries ‘uncle’” was cited in print in 1953. “This lady can squeeze a nickel so hard that the Indian cries and the buffalo sh**s!” was cited in 2007.
 
A similar saying is “He squeezes a quarter so tight the eagle screams.”
   
 
Wikipedia: Buffalo nickel
The Buffalo nickel or Indian Head nickel was a copper-nickel five-cent piece struck by the United States Mint from 1913 to 1938. It was designed by sculptor James Earle Fraser.
   
Google Books
Tramp Printer
By Harry J. Muntz
New York, NY: Pageant Press
1953
Pg. 91:
The father was the kind of man who squeezes a nickel so hard the Indian cries “uncle”.
 
Philly.com
FOOD
Tony’s: It’s A Real Slice Of Life (and Tomato Pie)
October 19, 1994 | by Gar Joseph, Daily News Staff Writer
I’m old enough to remember Saturday matinees for 50 cents and pizza slices for a quarter. My mom would drop me off at our old neighborhood theater so I could watch a Tarzan movie, a serial and cartoons while she worked as a waitress at a nearby restaurant to earn a few extra bucks for the family. I wondered whether such cheap entertainment could still be found. So I asked my colleague Phantom Rider, who knows how to make the Indian cry on a buffalo nickel.
 
Google Books
No Paltry Thing:
Memoirs of a Geezer Dad
By Larry L. Meyer
Huntington Beach, CA.: Calafia Press
2004
Pg. 137:
Okay, I’m stingy. The three sons of my first family referred to me as “penny-pinching Dad.” Guilty as charged. A friend at the time — this when Iron Eyes Cody had a TV spot shilling for the environment — upped the ante to a nickel when he observed that I “squeezed the buffalo so hard” I “made the Indian cry.”
 
Data Access Worldwide Forums
Cliff Little
1-Jun-2007, 10:24 AM
Exactly what I said to the Comtroller ... Miss Penny! This lady can squeeze a nickel so hard that the Indian cries and the buffalo sh**s!
       
Marks the Scot—Forum
auld argonian
30th November 07, 08:42 AM
(...)
4) ...and, of course, you also have the possibility that we are just a huge bunch of pathologically cheap and penurious bastards who can squeeze a nickel so hard that the Indian cries and the buffalo on the back side farts.