During a dance-dinner party with his boss at the Club Chateau one evening, he makes the acquaintance of a sweet society woman named Helen (Helen Vinson). She learns that Jim likes to "build bridges and roads for people to use when they want to get away from things," but that he feels destined to be locked down: " - but they can't get away, nobody can."

Together, they make a personal "getaway" and park in the moonlight by Lake Michigan, where he begins to fall in love with her:

Allen: Do you mind if we stay here awhile, or must you go home?
Helen: There are no must's in my life. I'm free, white, and twenty-one.
Allen: You're lucky.
Helen: Why?
Allen: Well, you can go where you want, when you want.
Helen: Can't you?
Allen: Yes - and no.
Helen: You're a strange, moody person. You need somebody to pull you out of those doldrums.
Allen: Are you applying for that job?
Helen: I might consider it.
Allen: You're hired.
Helen: When do I start?
Allen: You've started several hours ago.

1929's calendar months fly off the wall - August, September, October, November, and December, and into 1930 - January, February, and March [the start of the Depression]. As Marie lounges on their couch as he negotiates for a divorce, she disapproves of the split:

I told you I was satisfied with the way things are...I'm happy. I'm taking no chances of letting you go. Hey, listen. You're gonna be a big-shot some day with plenty of sugar, and I'm gonna ride right along. Get that? I'm no fool. I'd be a sucker to let you go now.

When he admits his love for another woman, she is unsympathetic with his plight ("That's just too bad"). So he threatens to divorce her if she won't listen to reason, and she determinedly counter-threatens him:

Allen: Why don't you play the game square?
Marie: Square! So that you and your sweet mama can give me the grand goodbye, huh? Ah, be yourself.
Allen: If you don't listen to reason, I'll find some way.
Marie: You do and you'll serve out your time.
Allen: It's no worse than serving out my time with you.
Marie: You'll be sorry you said that.
Allen: Now, listen, you've held a sword over my head about long enough. It's about time you called it quits. You've been pulling a bluff on me and I've been fool enough and coward enough to fall for it.
Marie: Oh, you filthy, good-for-nothing convict. A bluff, eh? You'll see. You'll see.

The next day, the Chairman of the Chamber of Commerce (Edward J. Le Saint) invites Allen to speak at a banquet, as a detective (Lee Shumway) bursts into his office and presents a warrant for his arrest. The camera zooms in for a close-up of Allen's stunned face. He has been informed upon by his blackmailing wife. A campaign is mounted to save Allen from being extradited back to the South to serve out his sentence:

Chicago Daily Tribune - Northern paper
CHICAGO FIGHTS TO KEEP ALLEN FROM CHAIN GANG!
Citizen Who "Made Good" Faces Prison

The Daily Courier - Southern paper
LOCAL CHAIN GANG OFFICIALS IRATE AS CHICAGO REFUSES TO AID THEM!
We Want Him Back!
James Allen Blocks Justice in Illinois

Allen speaks to reporters about conditions in the southern penal system, vowing: "Every thing I've said are facts. I want this rotten chain gang system exposed." Opposing editorials appear in the papers, one titled: "Is This Civilization?"

Shall we stand by while a man who has become a respected citizen of the community has the shadow of medieval torture again creeping over him? Must James Allen be sent back again to a living Hell? This is the question that Chicago officials must decide within the next few days. James Allen, a respected citizen of Chicago...

The other is titled: "What Has Become of State Rights?"

It is, indeed, a sad state of affairs when the governor of one state refuses to recognize the rights of another. What has become of state rights when this commonwealth is unable to extradite from Illinois a convict who has never paid in full...

In the offices of the Chicago District Attorney, the DA (Douglas Dumbrille) debates Allen's extradition. A southern representative proposes for Allen to voluntarily return to the state (and pay the expenses of the case), where he would be fully pardoned and exonerated after ninety days, working in some clerical job in one of the camps: (Supposedly, it's only a technicality: "No prisoner is eligible for pardon until he's served ninety days.") One of Allen's lawyers argues that his client shouldn't have to return at all: "Why mete out punishment to a man who has proven himself a useful and honorable citizen?" Allen's inclination, after speaking to fiancee Helen, is "to get it all cleaned up now, so that nothing will stand in the way of our happiness."

In Allen's absence, the representative even defends the chain gang system and preaches that it is beneficial:

Our chain gangs are beneficial to the convicts, not only physically but morally.

Allen voluntarily decides to give himself up and return - on the representative's assurance of a pardon, to wipe his past slate clean. He is told: "And you won't regret your decision."

A train takes him back to the South (a superimposed map displays his journey back there, fading out in Kentucky). In the office of Attorney at Law Mr. F.E. Ramsey (Robert McWade), Allen pays the expenses of his capture and return ($350) and his lawyer's fee ($2,500). Ramsey admits that nothing is assured, and the promised clerical job has probably evaporated:

This is a funny state, and the governor's a little peculiar. You see, all that publicity you gave out about the conditions here didn't help any...They might want you to work for about 60 days.

In the Tuttle County Prison Camp (with 69 Negroes and 33 White prisoners), Allen learns that promises have not been kept. He has not been made a trusty, but has been reassigned right back to an even tougher chain gang. Conditions are revealed to be no different in the bunkhouse as the camera pans through the filthy, grimy place. Bomber recognizes his freed pal:

Bomber: How did you get to this little bit of heaven, kid?
Allen: That's a long story.
Bomber: ...Boy, if you think those other chain gangs are tough, wait till you get a load of this joint. These are the guys that were too tough for the chain gang.

The other inmates are incredulous that he believes that the state will pardon him from this ultimate of hellholes.

Allen's case is heard in the prison board, with the chairman (Willard Robertson) presiding. Ramsey introduces Allen's brother to speak on Jim's behalf. The Reverend's demeanor is weak and unconvincing:

...the story of James Allen as a human being - a man of essential fineness and integrity of character. A man who was decorated for bravery in the world war. A man who committed a crime, but only when forced to at the point of a gun. His first and only offense. A man who showed his true character by rising from less than nothing to become a prominent and honored citizen.

Ramsey concludes the proceedings: "I need not remind you that James Allen has kept his part of the bargain. He has returned voluntarily to this state and has paid all the expenses demanded of him. I cannot believe in the light of all this evidence and in the name of justice that you will bring yourselves even to consider any other alternative." The Chairman reminds the board of Allen's "malicious and unwarranted attack upon the chain gang system," and denounces him for his grossly exaggerated criticism of the penal system. He even uses Allen's own life story as proof that the chain gang rehabilitated him:

The life of a convict in a chain gang is one of hard labor. The discipline is strict but there is no brutality. The purpose of prison is not only to punish crime but to discourage it. And there is less crime in this state in proportion to her population than into 40 other states in this Union. Finally, as evidence of the chain gang's value as a character builder, I have but to present to you the very case that has been presented to us today, the case of James Allen, who entered the chain gang as a worthless tramp, and who left it to become one of a great city's most worthy and respected citizens.

When Rev. Allen imparts the decision of the Prison Board to his brother, and Jim learns that his pardon has been refused, he bitterly complains about nine more years of confinement:

The state's promise didn't mean anything. It was all lies! They just wanted to get me back so they can have their revenge, to keep me here nine more years. Why, their crimes are worse than mine, worse than anybody's here. They're the ones that should be in chains, not we!

He ultimately resigns himself to his fate, to be a "model prisoner" for nine more months to pay his obligation "in full" to the state (a year minus three months already served). His brother persuades him to "be honorably free" and supported by legions of fans throughout the country who will force the state to release him:

Nine months of this torture! I won't do it. I won't do it, I tell ya. I'll get out of here. Even if they kill me for it...All right. I'll wait nine more months. I'll be a model prisoner if it kills me.

Calendar months pass once more, from July to March, another nine months. Ramsey argues again before the stern-faced Prison Board that Allen has been a model prisoner - patient without complaining, with support from prominent individuals and organizations: "I think it only just, your honors, that he be given his freedom while there is still time for him to regain his former position in society of prominence and universal respect."

As a result of a final report from the authorities on his new hearing, Allen is told by the warden in the bunkhouse: "They've suspended decision indefinitely." He is crushed - his face grimacing with pain and hurt. His hopes are dashed permanently.

Allen makes a second, sensational jail-break escape with Bomber. They steal a truck carrying a case of high-explosive dynamite and blow up a bridge [opposite to his chosen profession, as he literally burns his bridges to society] to seal off the pursuit of guards, and Bomber is shot dead. Headlines read:

CONVICT MAKES SECOND ESCAPE - Daring Escape Causes Police to Tighten Net, Many Men Added to Search
JAMES ALLEN IS AT LARGE AGAIN - Desperate Convict Denied Pardon, Blows Up Bridge in Escape, Pardon Denial Proves Disastrous
CONVICT ESCAPES; BLASTS BRIDGE, Authorities Are Sure of Allen's Recapture

A Depression-era Editorial Asks: "What has become of James Allen? Is he, too, just another forgotten man?"

A little more than a year ago, James Allen made his second spectacular escape from the chain gang. Since that time, nothing has been heard of him and it now appears that the Allen case will go down in the state's history as one of the most mysterious of all.

In a famous unforgettable, and unhappy dubious ending, as a harried and frightened convict hunted like an animal by police for over a year, a desperate and victimized Jim emerges from hiding one night in the shadows to see his fianceé Helen for a brief final farewell and a few words:

Helen: Jim, why haven't you come before?
Jim: I couldn't, I was afraid to.
Helen: But you could have written. It's been almost a year since you escaped.
Jim: But I haven't escaped. They're still after me. They'll always be after me. I've had jobs but I can't keep them. Something happens. Someone turns up. I hide in rooms all day and travel by night. No friends. No rest. No peace.
Helen: Oh, Jim!
Jim: Keep moving. That's all that's left for me. Forgive me, Helen. I-I had to take a chance to see you tonight. Just to say good-bye.
Helen (She hugs him with a look of intense suffering and pity on her face): Oh, Jim. It was all going to be so different.
Jim: It is different. They've made it different....(A door slams) (He whispers) I've gotta go.
Helen: I can't let you go like this!
Jim: I've got to.
Helen: Can't you tell me where you're going? (He shakes his head no and stares wildly at her.) Will you write? (He backs up and again shakes no.) Do you need any money? (He again shakes no.) But you must, Jim. How do you live?

The final line of the film is his reply as he totally vanishes and delivers a postscript from within the dark abyss of shadows:

I steal!

[Note: The composition and lighting of this abrupt scene, considered one of the most effective endings in film history, was actually an accident. Reportedly, the lights on the set were turned out prematurely (or failed, depending on the anecdote), but upon seeing the stark scene that resulted, the studio decided to keep the error in the final film.]