Ride with the Devil

In April 1861, the Civil War erupts in the United States, drastically altering the lives of many, including two friends from Lexington, Missouri. Jake Roedel and Jack Bull Chiles find themselves on opposing sides of a growing conflict that will test their bond and influence their futures.

The peace of the Chiles family is shattered when a group of Jayhawkers attacks their plantation, resulting in the devastating murder of Jack's father. In the wake of this tragedy, Jack and Jake make the difficult decision to flee their home and seek refuge elsewhere.

A year later, Jake and Jack conscript into the First Missouri Irregulars, a Confederate militia unit under the leadership of John Ambrose. The young men become embroiled in guerrilla warfare, fighting against the Jayhawkers and wrestling with their own moral dilemmas.

During their time with the Irregulars, Jake faces a critical choice when he spares the life of Alf Bowden, a Unionist neighbor. Unfortunately, this kindness comes back to haunt him when he discovers that Alf later avenged himself by killing Jake's father.

To escape the harsh winter, Jake, Jack, Holt, and Clyde take refuge in a dugout on the Evans family property. While these tensions brew beneath the surface, romantic relationships develop, particularly between Jack and the widow Sue Lee, adding layers of complexity to their situation.

The fragile peace is shattered when a Jayhawker attack destroys the Evans family home, resulting in the death of the patriarch and leaving Jack severely injured. As the group struggles with the consequences of this violence, trust issues arise when Clyde abandons them at a critical moment.

In a race against time, after being left behind by Clyde, Jake and Holt try to save Jack’s life by amputating his arm. Tragically, their efforts are in vain, and complications from gangrene lead to Jack's eventual death, deepening Jake's sense of loss and betrayal.

In search of answers and a way to cope with their losses, Jake and Holt align themselves with guerrillas under Captain William Quantrill. They prepare for an infamous raid on Lawrence, Kansas, setting the stage for one of the Civil War's bloodiest confrontations.

The chaos that ensues during the Lawrence raid sees the pro-South forces devastate the town, killing many, including Union supporters and black freedmen. With their morals challenged, Jake and Holt manage to avoid the frenzy, choosing instead to take shelter in a nearby restaurant.

As the group escapes from Lawrence, a confrontation with the brutal Pitt Mackeson unfolds. The tension mounts as Jake and Holt find themselves facing Mackeson at gunpoint, ultimately forcing him to retreat and leaving behind unresolved animosities.

In the aftermath of the raid, Union troops relentlessly pursue the guerrilla fighters, leading to further conflict. Tragedy strikes again when Clyde, trying to aid Holt after he is shot, suffers a fatal injury, compounding the grief already felt by Jake.

In the midst of loss, a new life emerges as Sue Lee gives birth to Jack's daughter, Grace Shelley Chiles. This event renews discussions about marriage and family, pressing Jake into a reluctant role as Sue Lee’s protector amid their turbulent circumstances.

With Jack and Clyde gone, Jake grapples with the uncertainty of his future. After being introduced to Reverend Horace Right, he finds himself pushed towards marrying Sue Lee, ultimately leading to a relationship based on care rather than mere obligation.

As Jake embarks on a journey to California with his new family, he marks this new chapter in his life by cutting his hair, a personal promise made during the turmoil of war. This act symbolizes his evolution from a soldier to a family man.

At a crossroads, Jake and Holt share a poignant farewell as Holt decides to head to Texas to save his mother from slavery. The two friends leave behind a world steeped in conflict, each embarking on a new journey filled with uncertainty and hope.