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1.
outlaw. Current literature indicates that desperado is derived from the spanish term desesperado which means a person with no hope. The term comes from esperanza which means hope. Adding “des” to the front makes it an antonym. Changing the ending “anza” to “ado” makes it an adjective and desesperado means a person with no hope. While this may be logical, it intuitively does not seem to fit well. I sounds like an Ivy league researcher explanation. I spoke with Native American oral historian and their oral history says that the term evolved in this fashion:

Spain created the Camino Real from Mexico to Santa Fe, New Mexico, in 1598. Camino Real literally means “Royal Road”. As such the road is protected by garrisons at intervals along the road. Spanish law levied a toll to travelers on the Camino Real in order to pay for these soldiers. The soldiers would stop the travelers and demand the toll be paid for them to continue on. In spanish “to stop” is “parar”. And as above “desparado” is a person that was not stopped. According to their oral history, the term desparado, described travelers that did not want to pay a toll and circled, off the road, around the military posts. The term became associated with “scofflaws”, people that openly disrespect the law. When the Americans immigrated into the area they modified the language of the region to suite. Words like “la reata” in Spanish became “lariat” and desparado became desperado. To me this explanation makes a better fit, desparado meaning law breaker is a better fit than desesperado a “a person with no hope”.
Desperados have been depicted in Western literature and film for decades. The movie Desperado is about a cowboy character running from the law. Which is appropriate for a person that shot the sheriff. He is a desperado, an outlaw.

The Eagles song Desperados has lyrics describing a cowboy wandering the range "out mending fences". This is not appropriate. Desperados are not necessarily cowboys. I thing the Eagles missed the target to this one.
by Francisco Osuna January 24, 2007
158 58
 
2.
a desperate criminal, so says the real one,
somebody who lives their life alone, but is desperate to be loved.
by the great April 22, 2005
88 65
 
3.
A desperado is a kind of joint. When someone runs out of weed, with little hope of weed in the immediate future, they may opt to roll and smoke a desperado, which is a joint made up of all the joint-ends in the ashtray, the scrapings-out of all the weed baggies lying around, and pretty much all the weed from everywhere that there might be weed.

It's never really worth it - it's normally completely minging, and it can be a bit of an effort finishing off a desperado because it is the pinnacle of horrible. It might get you a tiny bit stoned, but you'll probably be so miserable after smoking something so horrible that you'll want to die.

Actually, fuck it. It's always worth it.
Dear Diary,

It's been eighteen hours since I ran out of weed. I've been in a cold sweat for forteen of them, and I've already clawed out my left eye. The only thing I can think of doing is smoking a desperado, although it'll make my fingers smell, half of it will be ash, and I probably wont get stoned at all. But at least it's something to do!

I'm sinking deeper and deeper into withdrawal. I NEED A DESPERADO NOW.

Signing off,

John Major.
by Earfetish August 13, 2005
83 81
 
4.
A male who, by virtue of the sheer volume of girls he flirts with, is able to hook up often. However, because of his lax standards, these invariably end up in the 1-5 range.
Man, you see that butterface Mike's getting with? What a desperado!
by whathaveyou32 September 28, 2010
29 37
 
5.
Someone who is desperate for a boyfriend/girlfriend, when really they just want attention from the opposite sex for reassurance.

Someone who acts "desperate" for a boyfriend/girlfriend and denies it.
Alicia be actin' like a damn desperado with her damn hair flipping.

He looks like a desperado just trying to talk to Jessica.
by BooBooChaquita February 02, 2011
10 20
 
6.
bandits in da club, playground, or workplace. usually of mexican/indian decent. also refers to an imprisoned white adolescent.
i ain't no straight cat, i be a desperado.

dude, keep your eye on that desperado
by Fuzzle Puppy February 13, 2009
6 17
 
7.
If you have not been laid in at least 6 months the desperado rule takes effect meaning that anyone/anything you sleep with will not be held against you.
You slept with WHO?

I know dude, I know, but its been a long time since I've got any!

Hey, desperado rule man. I guess sometimes you got to lower quality to get quantity...
by Todays_Chaos August 18, 2008
14 24