“Professional homeless” seems like an oxymoron. Who is “professionally” without a profession and a home?
 
The term “professional homeless” has been cited in print since at least 1982 to describe people who are homeless for a long period of time, never looking for work but always looking for handouts. At the 2011 “Occupy Wall Street” protests, free food was given to the protesters, but efforts were made to separate protesters from the “professional homeless.”
 
 
Google News Archive
9 February 1982, Lakeland (FL) Ledger, pg. 1B, col. 1:
Tuesday’s results: Do you think communities have a responsibility to provide food and shelter for the homeless”
(...)
No, a Ledger reporter recently showed us how the professional homeless live off the community just as a way of life. We don’t owe them anything.
 
Google Books
Contemporary Astrological Observations Times
Volume 6
1984
Pg. ?:
Decades ago, when I was just getting the hang of astrology, I went to live on The Bowery amongst the professional homeless.
 
Google Books
The Case for Hanging Errant Public Officials
By James Farrell
San Francisco, CA: Fulton-Hall
1988
Pg. ?:
These are what might best be called the “professional” homeless, the legacy of decades of both political and economic brainwashing that has made being perennially poor a virtue rather than what it really is — a serious lack of character.
 
Google News Archive
23 November 1988, The Item (Sumter, SC), “Shelter for homeless survives without government assistance,” pg. 10C, col. 4:
Frank screens potential residents to separate those she calls the professional homeless from the truly needy, the recovering drug addicts from those who don’t want to recover, the unemployed from the unmotivated.
 
Google News Archive
21 May 1990, Hendersonville (NC) Times-News, “The professional ‘homeless’” by Andy Rooney, pg. 18, col. 2:
We have a whole class of professionally homeless people who are good at it. It’s their life. When they wake up over the grate or on the park bench in the morning, they don’t think about where to go look for work, they think about how they’re going to be homeless that day.
 
New York (NY) Times
Almost Homeless Again: Writer and Dog on Edge
By DAVID RAMPE
Published: January 01, 1998
(...)
The memoir is ‘‘a classic of down-and-out literature,’’ the essayist Phillip Lopate wrote.
 
But Mr. Saylor says ‘‘Lizbeth’’ painted Mr. Eighner into a corner. ‘‘What was he supposed to write about?’’ he asked. ‘‘Life as a professional homeless person?’‘
 
New York (NY) Post
Occupy Wall Street kitchen staff protesting fixing food for freeloaders
By SELIM ALGAR and BOB FREDERICKS
Last Updated: 10:58 AM, October 27, 2011
Posted: 1:43 AM, October 27, 2011
The Occupy Wall Street volunteer kitchen staff launched a “counter” revolution yesterday—because they’re angry about working 18-hour days to provide food for “professional homeless” people and ex-cons masquerading as protesters.
 
For three days beginning tomorrow, the cooks will serve only brown rice and other spartan grub instead of the usual menu of organic chicken and vegetables, spaghetti bolognese, and roasted beet and sheep’s-milk-cheese salad.
 
They will also provide directions to local soup kitchens for the vagrants, criminals and other freeloaders who have been descending on Zuccotti Park in increasing numbers every day.