As they reach the Mexican border to take refuge in a village, Angel, the only Mexican in the group, recognizes differences from Texas at the edge of the border river, but not the Gorch brothers. Their conversation points out their cultural differences and varied perspectives:

Angel: Mexico Lindo.
Lyle: I don't see nothin' so 'lindo' about it.
Tector: Just looks like more Texas far as I'm concerned.
Angel: Aw, you don't have no eyes!

In a poor Mexican village, they meet up with veteran comrade Sykes (Edmond O'Brien), a grizzled ex-member of the gang (reminiscent of old prospector Howard in John Huston's The Treasure of the Sierra Madre (1948)), who has fresh horses and saddles ready for them. There, the outlaws argue over how to split the stolen money. The trigger-happy Gorch brothers claim that an inexperienced Angel (on his first raid) and the "old goat" Sykes should both have a smaller share of the loot, but Pike quickly silences their greed and takes Angel's side:

Lyle: So we decided. It ain't fair.
Pike: If you two boys don't like equal shares, why in the hell don't you just take all of it? Well, why don't you answer me, you damn yellow-livered trash!...I don't know a damn thing, except I either lead this Bunch or end it right now.

When they slit open the canvas money bags, all they find are worthless metal washers, not even "silver rings." The revelation of the trap that ensnared them threatens to upset Pike's leadership and judgment and the camaraderie of the Bunch:

Dutch: Silver rings, your butt! Them's washers! Damn!
Pike: Bastards!...
Lyle: We shot our way out of that town for a dollar's worth of steel holes.
Pike: They set it up.
Lyle: They? Who in the hell is 'they'?
Sykes (laughing uncontrollably with his tobacco-stained mouth wide open): 'They'? Why, 'they' is just plain and fancy 'they.' That's who 'they' is. Caught you, didn't they, eh? Tied a tin can to your tail. Led you in and waltzed you out again. Ha, ha, ha. Oh my, what a bunch! Big, tough ones, eh? Ha, ha, ha. Here you are, with a handful of holes, a thumb up your ass, and a big grin to pass the time of day with. They? Who the hell is 'they'?
Pike: Railroad men, bounty hunters, Deke Thornton.

When the group considers their next move, Pike suggests: "Maybe a payroll, maybe a bank," but they all realize that as aging gunslingers and with the rising tide of modern life, their tired days are numbered:

Tector: That damn railroad you're talkin' about sure as hell ain't a-gettin' no easier.
Sykes: And you boys ain't a-gettin' any younger either.
Pike: We've got to start thinkin' beyond our guns. Those days are closin' fast.

Around the bounty hunters' night campfire, Coffer asks Deke Thornton about Pike:

Coffer: You rode with, uh, Pike. What kind of man we up against?
Thornton: The best. He never got caught.

In a parallel scene around the outlaws' campfire, Pike dreams of one final, successful job before retiring:

Pike: This was gonna be my last. Ain't gettin' around any better. I'd like to make one good score and back off.
Dutch: Back off to what? (No answer) Have you got anything lined up?
Pike: Pershing's got troops spread out all along the border. [The U.S. Government called out its army, led by General Pershing, to defend its borders against the raids of Pancho Villa, one of several Mexican revolutionary leaders.] Every one of those garrisons are gonna be gettin' a payroll.
Dutch (sarcastically): That kind of information is kind of hard to come by.
Pike: I didn't say it's gonna be easy but it can be done.
Dutch: He'll be waitin' for us.
Pike: I wouldn't have it any other way.

Doubting his own ability to make sound decisions as he grows older, Pike's (and Deke Thornton's) memories drift into a shared flashback of the same memory. As ex-partners and outlaws, they both remember Pike's prideful overconfidence ("Being sure is my business!") and lapse in judgement in a bordello, when he suggests that the authorities wouldn't look for them in a whore house. Thornton is more apprehensive - and with good cause, when a Pinkerton agent bursts through the door. The confrontation resulted in Deke's wounding, capture by the law and subsequent imprisonment in Yuma Prison, while Pike escaped from the authorities and abandoned his friend.

Dutch asks whether Pike learned from his ill-advised decisions of the day's bank robbery:

Dutch: How about us, Pike? You reckon we learned, bein' wrong today?
Pike: I sure hope to God we did.

On his back and staring straight up, Dutch sympathetically affirms Pike's earlier statement, and then rolls over to go to sleep with his back to Pike:

Pike, I wouldn't have it any other way either.

On a treacherous ride along the crest of a desert sand dune the next day, Sykes spooks the horses and sends all of them cascading down the sandy hillside. Pike intervenes and prevents Tector from killing the old man, citing his belief in the old Western creed/code of loyalty and dedication:

We're not gonna get rid of anybody. We're gonna stick together, just like it used to be. When you side with a man, you stay with him. And if you can't do that, you're like some animal. You're finished! We're finished! All of us!

[His belief in the code is sharply contrasted to his previous abandonment when Thornton was captured.] Pike's stirrup breaks as he mounts his horse, and an old leg wound is reinjured when he forcefully hits the ground. [A future flashback will reveal how Pike was wounded.] The Gorch brothers speculate about new leadership to replace Pike by taunting:

Riding with Brother Pike and old man Sykes makes a man wonder if it ain't time to pick up his chips and find another game.

They watch the unresponsive outlaw leader painfully mount his horse, turn, and ride off majestically ahead of them into the distance. As they ride along, Pike tells Sykes of his duty-bound allegiance: "We started together. We'll end it together." To Pike's surprise, Sykes reveals that Crazy Lee, abandoned in the bank, was his reckless, unreliable grandson: "My daughter's boy. Not too bright, but a good boy." Undoubtedly, Pike is reminded of how he left Crazy Lee to die - and violated his own code of loyalty. Sykes wants to know how the boy performed in the robbery: "I just wanted to make sure he didn't let you down, run when things got hot." Pike responds, after a rapid dissolve flashback of his order "Hold 'em here" to Crazy Lee: "...he did fine, just fine."

When the bounty hunters reach the Mexican river border crossing in their pursuit of the outlaws, Coffer tells Thornton:

Coffer: From here on, it's Mexico, Mr. Thornton.
Thornton: What's the closest town of any size?
Coffer: Agua Verde.
Thornton: What's in Agua Verde?
Coffer: Mexicans. What else? (Laughter) The headquarters for regulars, fightin' against Villa. Mapache territory.

Thornton turns his horse around and gallops off, telling the bounty hunters they must retreat and wait.

As the outlaws ride into Angel's village to spend their second night, the villagers eye them warily from behind village walls. There, they learn from the village elder and peasant revolutionary Don Jose (Chano Urueta) that the village was victim to civil war - and the revolutionary Mexican forces of 1913, federal troops (Federales) commissioned by the "traitor" Huerta and led by a self-appointed, corrupt warlord named Generalissimo Mapache (Emilio Fernandez). Seven of the villagers were killed, two of them were hung. Horses, cattle, and corn were stolen: "In Mexico, senor, these are the years of sadness, but if we had rifles like these..." To his sorrow, the principled Angel learns that his father "died like a man," and that his idealized "goddess" girlfriend Teresa (Sonia Amelia) went willingly along with Mapache and became his woman ("drunk with wine and love").

In contrast, Pike laughs heartily when he sees the Gorch brothers peacefully flirting with one of the young Mexican ladies, and innocently playing cat's cradle - a children's game:

Pike: Now that I find hard to believe.
Don Jose: Not so hard. We all dream of being a child again, even the worst of us. Perhaps the worst most of all.
Pike: You know what we are then.

Angel is overcome with rage over news of his girlfriend's leaving with Mapache, and vows to find him, but Pike points at him and forbids him: "Either you learn to live with it or we'll leave you here." After an evening of celebration, music, carousing and dancing, the Bunch are given a romanticized, ceremonial farewell (La Golondrina, a wanderer's love song) by the villagers, as the outlaw band leaves the next morning from the idyllic, pastoral place.

They push on to Agua Verde, another Mexican town, the location of Mapache's compound filled with Federales, to ostensibly sell their extra horses. Once there, Mapache makes his dramatic entrance into the town's gate in a shiny-red, open-top touring car [a symbol of advanced technology encroaching even into Mexico], causing a startled Dutch to respond to the strange vehicle that honks: "Now what in the hell is that?" Other machines are appearing in their world as well - airplanes.

The "generalissimo" warlord, with German connections/advisors, is a petty tyrant to Dutch - "just another bandit grabbin' all he can for himself," although Dutch objects to Pike's comment about being compared to the ruthless Mapache:

Pike: (cynically) Like some others I could mention?
Dutch: We ain't nothin' like him. We don't hang nobody.

When Angel's girlfriend Teresa presents Mapache with a present of a "pretty good-lookin' pony," Angel impetuously calls out to her, but she soon turns toward Mapache's banquet table and sits in his lap, sensuously licking inside his ear. The woman's flaunting of herself is commented upon by the wisecracking Gorch brothers, who ridicule the situation and further deepen Angel's hurt and pride. Jealously enraged that she is "very happy" with the general, the impetuous Angel calls out "Puta" (whore), and shoots his ex-girlfriend dead in the chest. Realizing they are in grave danger, the outlaws raise their hands to escape sudden annihilation by Mapache's men (who believe that the target was Mapache himself). One of the German advisors, Commander Frederick Mohr (Fernando Wagner) suspects that they are U.S. soldiers after identifying the Army weapons in their possession, but he adds: "It would be very useful for us if we knew of some Americans who did not share their government's naive sentiments." Since neither of them have much in common with the U.S. government, and the Bunch wishes to avert a bloodbath over Angel's behavior, they decide to share a drink with the Generalissimo and the manipulative German, while Angel is dragged away to be beaten.

The German advisor Mohr and Mapache's Lt. Zamorra (Jorge Russek) hire the fugitive Wild Bunch (for $10,000 in gold) from the neutral United States, to steal a shipment of guns and ammunition for the General from an American Army munitions train. Pike remains loyal to the captive Angel, arguing that they need him released and returned to them - and he is granted his request ("He is not important to me", Mapache offers). Given the circumstances, Pike's extraordinary loyalty for the youngest and most expendable of the bunch is commendable. In a playful interlude scene before fulfilling the contract for Mapache, the men enjoy the company of Mexican women, a shower of wine that trickles down from holes shot in the side of a wine barrel, and the comforts of a hot rocks steam bath.

In the steam bath, when Angel objects to stealing guns to kill his fellow countrymen, Pike conspires to let Angel steal one case of rifles and ammo for his own villagers:

Pike: I don't know why the hell I didn't let them kill you.
Angel: Listen, I'm not going to steal guns for that devil to rob and kill my people again.
Dutch: Noble, noble. Very noble.
Sykes: I didn't see no tears roll down your cheeks when you rode in from Starbuck.
Angel: Ah, they were not my people. I care about my people, my village. Mexico!
Sykes: Listen boy, you ride with us, your village don't count. If it does, you just don't go along.
Angel: Then I don't go along.
Dutch: Angel, one load of guns ain't gonna stop 'em raidin' villages. Well, you oughta be thinkin' about all the money you're gonna have.
Pike: Buy 'em a ranch. Move 'em a thousand miles. Buy 'em two, three ranches.
Dutch: One, a very small one.
Angel: Don't you see? This is their land. And no one is gonna drive them away.
Sykes: I'll drink to that sentiment. And to love. But most of all, I'll drink to gold. (They all drink)...
Pike: Angel, you're a pain in the ass.
Angel: Would you give guns to someone to kill your father or your mother or your brother?
Pike: Ten thousand cuts an awful lot of family ties.
Angel: My people have no guns. But with guns, my people could fight. If I could take guns, I would come with you.
Dutch: Hey, um, how many cases of rifles did Zamorra say was in that shipment?
Pike: Sixteen.
Dutch: Well, give him one.
Pike: All right. One case and one case of ammo. But you give up your share of the gold.
Angel: I will.
Pike: We know you will.

Still on the trail after the outlaws after six days of pursuit, railroad boss Harrigan is persuaded by Thornton to attempt another assault on Bishop. This time, it will be an expected train robbery for Mapache, described as:

...a killer for Huerta who calls himself a general. He's been fighting Villa - and losing. But with enough guns, he can become a power in northern Mexico. My guess is, Pike will try to get them for him.

But Thornton steadfastly refuses to work with his bounty hunters: "I need 20 trained men, not recruits. And not this gutter trash you've given me." Harrigan refuses.