Breckinridge Elkins, riding toward the town of War Paint, encounters Jack Sprague tearing up the trail with a rope in hand. He’s followed by Bill Glanton, who explains that Jack is heartbroken and intent on hanging himself after being jilted by a woman. Determined to prevent the suicide (partly because Jack owes him six dollars), Bill enlists Breckinridge’s help.

They track Jack into the Humbolts, where he’s preparing to hang himself from a tree on a cliff. Bill tries to distract him while Breckinridge circles through a thicket—only to accidentally awaken the infamous cougar "Old Brigamer," resulting in a brutal, slapstick fight. Breckinridge subdues the cat and reaches Jack just as he jumps from the ledge. With Breckinridge's brute strength and Bill’s knife, they save Jack, though not without injury.

Jack resents being saved, but Bill insists they take him away until he regains his will to live. Breckinridge suggests a hunting trip to the high Humbolts. There they run into old Joshua Braxton, a notorious bachelor hiding from marriage-minded women. With news that the local schoolteacher Miss Stark has moved away, Joshua is ready to return to civilization—until he hears a young, beautiful schoolmarm from the East is replacing her. Alarmed, he decides to stay in hiding.

Breckinridge, upon hearing of the new teacher, declares Bear Creek must have its own school and plans to recruit her. Bill, Joshua, and the reluctant Jack join him. The group sets off in a battered, slapstick caravan, with Cap’n Kidd—the violent horse—causing chaos all the way. They encounter settlers who mistake them for a wild war party and raise a town-wide panic.

The townspeople of Chawed Ear are ready to greet Miss Devon, the new teacher, with speeches and celebration, but flee when warned of the incoming "war party." A wild chase ensues. Breckinridge and his gang crash into the welcoming party, mistaking it as a threat, and chaos erupts. In the confusion, Breckinridge captures the stagecoach carrying Miss Devon and takes off with it, hoping to deliver her to Bear Creek and establish a school.

After a comic brawl and daring escape, Breckinridge proposes to Miss Devon that she become Bear Creek’s teacher. Initially stunned, she reluctantly agrees to go along, though clearly overwhelmed. Meanwhile, Jack Sprague and Miss Devon, left alone with the stagecoach while the others hold off the pursuing mob, fall for each other. They elope to War Paint, leaving a note behind.

The tale ends with Breckinridge discovering the note, outraged at the betrayal and dismayed that both his plans for culture on Bear Creek and his hopes for romance have been derailed.