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The story of the real Quantrill's Raiders is not an easy one to bring to the screen. The movie either has to have Quantrill, a sadistic and brutal man, at its center, or make him a supporting character in a movie where a good guy can hunt him down. The first movie sounds like the more interesting one but the second movie would probably cause less offense. Quantrill's Raiders from 1958 has it both ways by providing a protagonist that exists on the fence, straddled between supporting Quantrill or working against him. It's a fine line and the perfect balance that the story needs.
The real William Quantrill was a Confederate sympathizer who ran raids along the Missouri Kansas border during the Civil War. Those raids led up to his horrifying raid on Lawrence, Kansas, which was firmly anti-slavery, where he and his men murdered almost 200 civilians. Playing him in the movie, and doing a good job of portraying a man of that low caliber realistically, is Leo Gordon, the man Don Siegel once described as the scariest man he'd ever met. Gordon himself had been a criminal (convicted for armed robbery before his movie career) and if anyone could play someone like Quantrill at the time, it was Gordon.
But to make the story palatable to a wider audience, another character was introduced, one that would work with Quantrill but have ethical conflicts that would turn him around. That character, Westcott, played by Steve Cochrane, is the center of the movie and the ambiguity of his character makes the movie more suspenseful than it otherwise would have been, since the history is already known.
The movie begins with a line of Union cavalry moving through Missouri on their way to find Quantrill. Westcott (Steve Cochran) pulls up and presents papers showing he is a horse supplier for the Union. They let him join the line and make their way to a ridge where Quantrill's men ambush them. During the fight, both sides lose men with Westcott even suggesting a plan to the Union commander that ends the standoff, further cementing his credentials to the commander. Later, when they reach town, the judge who is helping to uncover Confederate sympathizers suspects Westcott might not be on the up and up and lets him know it. When he falls in love with the judge's daughter, things get complicated.
Steve Cochran was a good choice to play the villain/hero since he'd played so many villains before and the audience expected it. And while he never became a huge star he was legendary in Hollywood nonetheless. His legend came from his womanizing more than anything else. On and off the set he was considered a true ladies man but in the movies never became much of a sex symbol. He played so many heavies because he didn't have the kind of roguish charm that turned former heavies like Clark Gable and Humphrey Bogart into stars before him. And sadly, he took his love of womanizing to such extremes that it led to his death in 1965. After taking on an all-female crew for his yacht, none of whom actually knew anything about yachting, he set sail for Guatemala from Acapulco, and when he became seriously ill, no one on the yacht but him knew how to sail it. He died from his infection and the yacht drifted aimlessly for over a week, with his corpse onboard, before the "crew" was discovered and rescued.
The real standouts of Quantrill's Raiders are Leo Gordon and Will Wright. Gordon was perfect for the part and plays Quantrill with so much dripping slime and sleaze that the viewer feels dirty just watching him on the screen. As for Will Wright, one of the greatest character actors in all of Hollywood, his judge is the perfect balance of caution and action. He wants to protect his daughter but will do what he has to stop Quantrill. Rounding out the cast are Diane Brewster and Gale Robbins, the two love interests of Westcott and Quantrill, respectively, and in a small role, Glenn Strange, better known to most classic movie fans as the other guy who played Frankenstein's monster. Directed ably by Edward Bernds, who is most famous for directing the Three Stooges several times, the movie is exciting, suspenseful, and the best balance one could bring to a story with such unsavory characters.