“Nail them and jail them” (or “nail ‘em and jail ‘em”) is a policing method. Three terms are often used in the saying, such as “tail ‘em, nail ‘em and jail ‘em,” “trail ‘em, nail ‘em and jail ‘em,” and “surveil ‘em, nail ‘em and jail ‘em.”
 
“Nail ‘em and jail ‘em” has been cited in print since at least 1921. “The old ‘Nail ‘em’ and ‘Jail ‘em’ operation” was cited in 1971. “Trail ‘em, nail ‘em, and jail ‘em” was cited in 1991. “Tail them, nail them and jail them” was cited in 1994. “Trail ‘em, Surveil ‘em, Nail ‘em, and Jail ‘em” was cited in 1998.
 
   
The Free Dictionary
nail-em-and-jail-em and nailer
n. the police in general; a police officer. Old nail-em-and-jail-em is going to be knocking at your door any day now. Victor mooned a nailer and almost got nailed.
 
29 May 1921, Illinois State Register (Springfield, IL), pg. 4, col. 4:
NAIL ‘EM AND JAIL ‘EM
When fool drivers race their cars
Lock ‘em up.
They belong behind the bars;
Lock ‘em up.
 
15 September 1927, New Castle (PA) News, “The Road Hog” (poem), pg. 4, col. 4:
Let’s nail them, jail them, tie them up.
With other swine to dine and sup.
   
Google Books
California Youth Authority Quarterly
Volumes 24-25
1971
Pg. 33:
My main concern for the development of the treatment program for youthful drug offenders is that it not be one of the old “Nail em” and “Jail ‘em” operation.
 
Google Books
Signal Zero
By George Kirkham
New York, NY: Ballantine Books
1977, ©1976
Pg. 38:
“Dismissed. Nail ‘em and jail ‘em” he said.
   
Google Books
Runnin’ Down Some Lines:
The Language and Culture of Black Teenagers
By Edith A. Folb
Cambridge, MA: Harvard University Press
1980
Pg. 67:
... and the All Stars, Uncle Nab, nail ‘em and jail ‘em, Sherlock Holmes, and other expressions like pig heaven (police station) or Sam and Dave (partners in a patrol car).
     
28 April 1991, The Orange County Register (Santa Ana, CA), “Prison Reform: To stop the revolving door” by Chester Newland, pg. C1, col. 1:
Trail ‘em, nail ‘em, and jail ‘em.
 
1 June 1994, Cedar Rapids (IA) Gazette, “Corrections,” pg. 6A, col. 3:
Assistant director Jean Kuehl says there is an old stereotype about supervising clients—“you tail them, nail them and jail them”—where a supervisory officer often does little more than sit back and wait for a client to mess up enough to go to prison.
 
Google Books
The Expanding Prison:
The Crisis in Crime and Punishment and the Search for Alternatives
By David Cayley
Toronto, ON: House of Anansi Press Limited
1998
Pg. 43:
CRIME CONTROL IN THE UNITED STATES
“Trail ‘em, Surveil ‘em, Nail ‘em, and Jail ‘em”
 
Google Books
Resource Material Series
UNAFEI
Issue 59
2002
Pg. 138:
The slogan of one prevention service, I think in California is, “Surveil them, nail them, jail them”. It means “watch them”, “wait until they go the wrong way” and then “jail them” so that is not a vision of prevention service that I particularly look for.
 
Google Books
Problem Solving Courts:
A Measure of Justice
By JoAnn Miller and Donald C. Johnson
Lanham, MD; Rowman & Littlefield Publishers, Inc.
2009
Pg. 29:
To sum it up, using police jargon, a punitive response to drug offenders, and an appropriate one, is “Trail them, nail them, and jail them.”
 
Google Books
Justice & Is Just Us:
A Story for Anyone Who Believes in Change
By Harold B. Wooten
Bloomington, IN: iUniverse
2009
Pg. 247:
“Then I screamed something like, ‘Stop this tail ‘em, nail ‘em, jail ‘em punishment crap!”
 
Twitter
Anderson Publishing
‏@AndersonPubCJ
“Trail ‘em, nail ‘em and jail ‘em. That’s how we used to describe the old way of doing things” http://bit.ly/UaM9bc  #probation
7:55 AM - 15 Jul 2014
 
Google Books
American Corrections: Concepts and Controversies
By Barry Krisberg, Susan Marchionna and Christopher Hartney
Thousand Oaks, CA: SAGE Publications, Inc.
2015
Pg. 37:
Community supervision was dominated by a philosophy of “surveil them, nail them, and jail them.”