In 1851, Tom Dunson (John Wayne) and friend Nadine Groot (Walter Brennan), join a wagon train in St. Louis (or near St. Louis), headed for California. After three weeks, they approach north Texas, where the land looks good to Tom. He decides he wants to break away from the wagon train and go find a place to start a ranch of his own. The wagon master tries to order him to stay, then tries talking him out of it, all to no avail. Tom is also pretty handy with his fists and a gun, so there wouldnt be any forcing him.
Along with Tom and Nadine on the trip to California is Fen (Colleen Gray), Toms love interest. He and Fen are basically engaged (in love, anyway) and she wants to come with Tom and Nadine to find a ranch. Tom wont hear of it, promising to send for her once hes settled in. She doesn't like the idea of having to wait, but promises to come. Before leaving, Tom gives Fen a bracelet that belonged to his mother.
Tom and Nadine take off with their wagon, horse, one bull and two cows, and get maybe 10-15 miles from the wagon train, near the Red River, when they look back and see black smoke. Realizing that the wagon train has most likely been attacked by Indians, they know they cant get back in time to help, and that some of the Indians are likely to come looking for them soon enough anyway, so they set up in a defensive posture and wait.
Sure enough, maybe 6-7 Indian braves show up and begin an attack with a fire arrow that hits Tom's and Nadine's wagon (but doesnt do much damage). Both Tom and Nadine are good shots and they kill most of the attackers right away. However, one of their cows was killed by the Indians and then Tom has to fight hand-to-hand. He kills one Indian as they fight and fall into the river. Tom notices the Indian he killed was wearing the bracelet hed given to Fey. Tom then sneaks out to kill the last one or two Indians of the group, who were still out there hiding.
The next day, theres a young boy named Matt Garth (Mickey Kuhn) who comes strolling along leading a cow and talking to himself, like hes lost his mind. Tom slaps the kid to snap him out of his trance. The kid then pulls a hand gun and points it at Tom. Tom grabs the gun and takes it away, knocking the kid down. The kid is not crazy, but just play-acting. Tom tells him never to pull a gun on him again. The kid has spunk and tells Tom never to take his gun from him again. Tom turns to Nadine and says, hell do. Tom hands Matt's gun back to him and allows him to come with them. Apparently, the family or group Matt had been with was attacked by Indians too, so he had no one left.
The three of them travel deep into Texas, stopping at the Rio Grande, where Tom pronounces himself the new owner of all the land visible north of the river. He also says that 10 years hence, hell have the biggest and best ranch in all of Texas, with plenty of beef to feed and nourish all the people around the area. He tells Garth and Groot that he will brand all the cattle in his future herd with a D double bar (the bars representing the banks of the Red River). Matt wants an M added to the brand, but Dunson says he'll have to earn it.
Two Mexican men come riding up and introduce themselves as employees of Don Diego, the man who owns the land they are standing on. At that moment, Don Diego was at his ranch headquarters 400 miles south, in Mexico. Tom tells the two men to ride back and tell Don Diego that all the land north of the Rio Grande now belongs to him and hes taking it. One of the men says that just cant be and he goes for his gun. Tom outdraws him and shoots him dead. He tells the other man to take his friends horse and go back and tell Don Diego what happened. Tom told the guy that he would take care of burying the other man's body.
Flash forward nearly 15 years later to find Tom, Nadine and a grown Matt (Montgomery Clift) having a discussion about Matts recent return to the ranch, and the major problem of there being no market in Texas for all of Toms thousands of cattle (thanks to the Civil War basically bankrupting everyone). The decision is that they will need to drive the cattle north instead, to Missouri, to sell them. Tom was going to make Nadine stay behind, as Nadine was getting too old to ride, but the trail cook had just quit, so Nadine got to go, as the cowboys would need a cook.
Tom and Nadine had a funny exchange, right after Tom had told Nadine he had to stay behind. Nadine was talking to himself, complaining about the decision, while Tom was trying to talk to Matt. Tom finally turned to Nadine and asked him what he was saying and why didnt he have his new teeth in his mouth, because he couldnt understand his mumbling. Nadine responded that everyone else could understand him just fine and he was keeping his teeth in his pocket until he needed them for eating.
Matt was overseeing the branding of the cattle, preparatory to the drive, and having the men turn loose any cows belonging to a rancher named Meeker (Davison Clark), or to Don Diego. Tom rides up and orders that no cattle be turned loose and that they all be branded with the D-Double Bar brand (his). Matt doesnt agree, but tells the men to go ahead and do as Tom says.
About that time, Mr. Meeker rides up with some of his men, including a hired gun, and asks Tom for permission to look through the herd to cull out any of his cows. Tom denies permission, telling Meeker that hes branding all of the cows he has, regardless of any other brands they may already have on them.
Things get pretty testy and Matt and Mr. Meekers gunfighter, Cherry Valance (John Ireland) exchange words. Matt has become very handy with a gun himself. Tom relents somewhat, in that he decides to offer Meeker $2/head for any of his cows that make it to Missouri and get sold. Meeker agrees. Cherry then decides hed like to work for Tom instead of Meeker and asks to be hired on. Tom hires him at $10/month, the going rate for a trail hand.
Matt and Cherry are just itching to have a fight (preferably a gunfight), and Tom realizes its probably inevitable, but he forces them to get along for the time being. They do have an initial challenge contest, where they borrow each others guns and alternately shoot at a tin can, impressing each other with their respective skills.
In the bunkhouse, theres a poker game the night before the drive starts. Quo (Chief Yowlachie) is sitting opposite Groot. Groot has a good hand, but when Quo bets one silver dollar, Groot is aghast. Thats equivalent to 3 days pay. He asks Matt to loan him a dollar, but Matt refuses. The rule of the game is that only whats on the table at the time can be used to bet with. So, Quo asks Groot whats in the small bag he has there on the table and Groot tells him it contains his false teeth. Quo says hell accept half interest in the teeth to cover the one dollar bet. Groot isn't happy about it, but he agrees. They show their cards. Quo has the better hand and demands the teeth. Groot wants to know how hes supposed to eat without his teeth and Quo tells him that come grub time, you get em.
Dunson comes into the bunkhouse and tells everyone that its now or never as far as their decisions to go on the drive. He tells them that there will be no hard feelings for anyone who wants to stay behind, and promised them that theyd still have jobs on the ranch after the drive is over. He tells them that theyll be doing good to make 10 miles a day on the 1,000 mile drive, 15 miles if they are lucky. Theyll face bad weather, dust, Indians and border gangs (once they get close to Missouri). But, once a cowboy says hell go, hes expected to finish the drive, whatever happens. Dunson makes everyone going sign a piece of paper representing their word to stick it out.
The next morning, breakfast was served at 4:30 and, with nearly 10,000 head of cattle grouped together, at 5 a.m., Dunson quietly told Matt to take 'em to Missouri. All the cowboys whooped and hollered as they started out.
Quo holds Groot to the results of their bet, only loaning the false teeth back to Groot at mealtimes. Groot is not happy about that. He tells Quo that the teeth help him keep the dust out of his mouth. Quo tells him to keep his mouth shut then, and dust not get in. Groot complains that before the drive is over, hell probably eat enough land to get himself incorporated in the Union as the State of Groot. Quo still says no. Dunson isnt happy about the situation either, complaining that Groot mumbles and needs to have his teeth in to be understood.
The men start talking about taking the cattle to Kansas instead of Missouri, as its closer and there are less hazards along the way. However, because no one has personal knowledge of a railway actually being in Abilene, KS (where rumor has it there was one), Dunson says to forget it.
Dunson goes through 3-4 horses a day, so hes obviously very involved in the drive.
The group is 30 days into the drive with no major issues. One cowboy remarks that he doesnt like that. It makes him nervous. He prefers a balance of things going well and having trouble, not just one or the other. The trouble part does come, and it starts as a result of Bunk Kenneally (Ivan Parry) continuing to get into the supply of sugar (he dips his fingers into the sack whenever he can, which gets him in trouble with Groot). Everyone has been on their best behavior as far as being quiet, because the cattle are on edge. They are tired and there are coyotes milling about. Everyone is worried that the cows will stampede if something spooks them. So, when Bunk clumsily knocks over some of the cook pots as hes getting into the sugar, thats enough noise to start a stampede.
One of the cowboys prefers to wear a bowler hat. He gets trapped behind a shrub in the middle of the stampede, so Matt and another fellow ride up and each grab an arm of this fellow and they carry him off to the side of the stampeding cows and let him down.
After the cows are stopped and calmed down, it's noticed that one of the wranglers, Dan Latimer (Harry Carey Jr.) is missing. Latimer wore checkered pants and would talk about using the $100 he would be earning on the drive to buy a place to farm/ranch, and a pair of red shoes for his wife.
A search begins and they find what's left of Latimer's distinctive checkered pants among a bunch of dead cattle. Dunson tells Matt to make sure the widow gets Dans money and whatever else. Matt replies, like a pair of red shoes?
Dunson reads over Latimer's remains the next morning and as he puts the Bible back on the wagon, he goes over and picks up Groots' whip, at the same time calling out to Bunk: Bunk Kennally, you started all this! 400 cows dead and Latimer too. Stealing sugar like a little kid. Well, we whip kids to punish them for things like that.
Dunson tells Teeler to strap Bunk to a wagon wheel. Before Teeler can do that, Bunk speaks up and acknowledges that he is remorseful about Latimer and the dead cows, but he tells Dunson he wont stand to be whipped. As he goes for his gun, hed likely have been shot dead by Dunson, but Matt draws first and shoots Bunk in the shoulder, saving his life. Dunson turns to Matt and says, you shot him, you take care of him!
Matt provides Bunk with two horses and sends him back home. Cherry observes all this and tells Matt that while hes real fast with a gun, hes got a soft heart, and that will get him hurt some day. Matt says that could be, but not to count on it.
40 days out, with reduced rations (after one wagon was destroyed in the stampede), the men become increasingly restless. Tom reminds them that they all signed on to see it through, like it or not.
A cowboy named Sutter (William Self) rides up, his head bandaged and barely able to talk (there was a rope burn around his neck), saying he had been riding with the Garwood herd (2,000 cows) when they were ambushed by about 100 bandits. Hearing that, Naylor, Fernandez and another hand tell Dunson theyve had enough (but not until right after theyd watched Dunson set his gun belt down as he was preparing to go get some water). Dunson tells them they cant go. They reach for their guns as Groot tosses a loaded and cocked rifle to Dunson. Dunson's shots, in combination with those fired by Matt and Cherry, kill the three wranglers.
Dunson orders the three buried, announcing that hell read over them in the morning. That prompts one of the cowboys to say: Plantin and readin, plantin and readin. Why, when youve killed a man, why try to read the Lord in as a partner in the job?
Matt argues with Dunson over the need to confront and kill the three men. He and Groot both tell Dunson hes wrong to do such things. Groot then patches up a bullet wound on Dunsons lower left leg.
That night, Teeler, Kelsey and Laredo are on watch, when they decide to take some ammunition and flour and ride out, headed back home. The next morning, Dunson sends Cherry and Buster to go get the three and bring them back, dead or alive.
The herd arrives at the Red River. Matt wants to give everyone a rest and cross the river first thing in the morning. Dunson will have none of that, and orders the crossing to begin immediately. He finds a couple areas of quicksand in the river to be avoided then orders the crossing to start. The process continues into the night. Between 30-40 head are lost during the process.
Dunson is limping badly and pulls heavily from a bottle of whiskey once he sits down to rest. Hes exhausted, refusing to sleep until Cherry gets back with the three cowboys who left. He wants to make sure no one else tries to leave. Hes sure once the three are returned and punished, no one else will leave.
Cherry does come back, on the 4th day after he left, with two of the cowboys: Laredo and Teeler. Cherry said Kelsey chose not to return, so he had to shoot him. Dunson announces that he is going to hang the two. Matt tells him that he wont be doing that, and he will be the one to stop him. Dunson braces his right hand on a piece of wood to stand up and face Matt, but Matt shoots him in the hand. When Dunson tries to draw his gun, he isn't able to hold onto it and it falls to the ground. Dunson reaches down for it with his left hand and Buster shoots the gun away.
Matt announces that hes taking over and will be taking the herd to Abilene. He says that Dunson will be left behind. Groot offers to stay with Dunson, but he tells Groot to go with the others. He then tells Matt that hell come after him and will kill him.
Groot is later calculating how long before Dunson gets to another town, rounds up some new men, and catches up to them. For the next 2-3 weeks, everyone on the drive is nervous and jumpy, anticipating his return.
One of the steers is found dead, filled with Apache arrows. Matt sends Buster and Cherry ahead 10 miles with rifles to scout and keep watch. Buster comes riding back all excited, with news that theres a wagon train about 18 miles ahead, the Donegal party, headed from New Orleans to Nevada, to set up a saloon for gambling, drinking and partying. He says there are dancing girls with the wagon train. Matt decides that the men need and deserve some distraction and decides to head the herd to the wagon train before continuing on to Abilene.
As the herd approaches the wagon train, they hear shooting. The train is under attack by Apaches. Matt gives orders for the men to split into two groups and come at the Indians from the sides, while he and a few others ride down the middle. It takes some time to get all the men rounded up and ready, so Matt and the few others go ahead and ride straight to the wagons, jumping right into the middle of the circled wagons and helping fight the Indians who were circling around, yelping and shooting their arrows.
Matt finds himself side by side with a very attractive woman who is firing a rifle (but not very well). Shes Tess Millay (Joanne Dru). He tells her to load and hell shoot. She perceives that hes angry about something and wants to know what. About that time, she takes an arrow to the right shoulder, pinning her to a wagon. Matt cuts the shaft so she is free from the wagon, but he has to finish the Indian fight before helping more. The rest of the men finally come charging down the hill and the men within the circle of wagons come charging out and the Apaches decide to hightail it.
Matt returns to pull the arrow from Tesss shoulder, then he decides he needs to suck some poison out of the wound. She slaps him across the face for doing that, then passes out.
Theres a big party that night, making use of the food, drinks, cards, and girls that are all available in the camp. Tess asks Groot to tell her all about Matt, because she "needs to know." She also wants to talk to Matt before they get back on the trail the next day. Groot goes and finds Matt (hes out in the evening fog, on watch) and tells Tess where he is. She goes out there and gets up close and starts talking to him. She tells him that he needs to talk to her, that talking about his concerns and fears is the way to deal with them.
Matt doesnt need all that much convincing to talk, as she's a very soft and pretty girl that is very close to him. He opens up and they quickly get very comfortable with each other. Shed fallen in love with him immediately. He probably did too, but needed a bit of convincing that it would be ok to fall in love with a saloon girl.
As its raining hard and there are worries about the level of the next river to be crossed. Matt decides they need to do it right away, even though its nighttime.
Meanwhile, Dunson has gathered 8 new men and is on the chase. Nine days after the herd had left the wagon train, Dunson and his men come across the wagons. Tess immediately announces that shell "take care of Mr. Dunson." She considers shooting Dunson, as he sits in her tent talking to her, but he knows she has a pistol and is prepared to shoot her first if need be. It doesnt come to that. He notices shes wearing his mothers bracelet and asks her how she got it away from Matt. She sarcastically says she stole it, then admits she loves Matt and that he gave it to her.
As they talk, Tess tells Dunson that she wanted to go with Matt on the drive, but he said no, it was too dangerous and tough. That reminded Dunson of the day when he turned down his womans request to go along with him. He was nevertheless bound and determined to go find and kill Matt, and tells Tess she cant say or do anything to change his mind. She keeps after him, though, and he acknowledges his disappointment in Matt, saying he was the son he never had and would stand to inherit his ranch if he hadnt betrayed him.
Dunson takes a fresh look at Tess and offers her half of everything he owns in exchange for her bearing him a son. She says shell do it, if hell stop pursuing Matt. He says no, so she begs instead to be allowed to go with him. He says ok.
Matts understandably stressed about whether they will find a railroad in Abilene, and the fact that Dunson is hot on his trail. Fortunately, they hear a train whistle in the distance and come across a train, about 12 miles from Abilene. The engineer is very thrilled to see the herd, as are the townspeople who come riding out to meet and greet them. They tell Matt to drive the herd right down Main Street so all the people can see (thats nearly impossible not to do anyway, as its a tiny town).
Its August 14, 1865 and marks the time the first cattle drive on the Chisholm Trail is completed.
In Abilene, Mr. Melville (Harry Carey Sr.) represents the Greenwood Trading Company of Illinois and offers immediately to buy the entire herd. Matt has no experience at selling cows, so hes hesitant to accept the $20/head offer. Mr. Melville then tells him to go out and find the best price he can for a lot of 500 cows and then hed match the price and still buy the whole herd. It ends up being $21/head. Matt signs the contract and receives a check for $50,000, with the balance to be paid once a final tally is arrived at. He makes sure all the cowboys get paid right away.
Matt returns to his room at the Hotel Royale and is shocked to find Tess in there, all dressed in black. She apologizes for appearing as if shes in mourning. She tells him Dunson is camped outside town and will be coming to get him in the morning. It's likely that they get to know each other intimately that night.
The next morning, everyone has gathered at the front of the hotel, waiting. Buster rushes in through the cows on his horse to announce that Dunson and his 10-12 men were riding in. Dunson, meanwhile, is telling his men to remember where they each stand in all this, which apparently is to hang well back and not interfere. Dunson dismounts on the far side of the railroad tracks and sets out with a very purposeful walk, through the cows and across the tracks.
Cherry, realizing that Matt is not likely to draw and shoot it out with Dunson, confronts Dunson before he gets to Matt. They both draw and shoot, wounding each other. Cherry falls, but Dunson continues on. He gets close and tells Matt to draw, but Matt refuses. Dunson draws and empties his gun, shooting all around Matt, knocking his hat off and grazing his right cheek, drawing blood. He then walks up to Matt and wants to know what he has to do to make a man out of him.
Dunson grabs and tosses away Matts gun. He reminds Matt that as a boy, he once told him never to try that again, but Matt doesn't react. Dunson then punches Matt in the face 2-3 times, knocking him down. He drags him back up, ready to hit some more, but Matt shocks him by punching him and knocking him down. They brawl until Tess fires a pistol into the air, stopping the action. She chews them out loudly for awhile, then decides maybe they should go ahead and pummel each other, and she turns away so they can continue.
They don't start fighting again, however. Instead, they stand looking after Tess. Dunson tells Matt to marry that gal. Matt says, When are you going to stop telling people what to do? Dunson says, After one more thing. After we get back to Texas, Im going to make the brand the double bar D, with an additional name (he scrawls out an M in the dirt). You earned it!