Errol Flynn is Jeb Stuart; Ronald Reagan is George Custer. They’re West Point classmates, punished for getting into a fight over abolition with colleague Carl Rader.
Their punishment: Being assigned to serve at Fort Leavenworth after their graduation.
With Kansas torn over the issue of slavery, the Fort Leavenworth assignment was considered a dangerous one, made more so by John Brown (Raymond Massey) and his raiders.
But that assignment also allows the two ambitious young officers a chance to see action. And a chance to get reacquainted with the pretty sister of a fellow West Pointer, the tomboyish “Kit Carson” Holliday (Olivia de Havilland).
Stuart and Custer have their first run in with Brown while escorting a wagon train of supplies along the Santa Fe Trail. Stuart discovers that those supplies include rifles in boxes labeled as Bibles, prompting a skirmish between the supply train and Brown’s abolitionists.
Brown’s youngest son Jason winds up mortally wounded. Convinced his father is going about freeing slaves in the wrong way, he tips the army off to the location of his father’s headquarters.
That leads to a second battle. Brown escapes, but his headquarters is burned, his supporters scattered and his movement squashed. Or so the Army thinks.
Then comes the news that he’s planning an attack on the arsenal at Harper’s Ferry, hoping to spark a slave revolution in the process.
Having been sent back East, Stuart and Custer are again called on to respond to the threat.
Errol Flynn as Jeb Stuart, coming face to face with John Brown in Santa Fe Trail (1940)
Olivia de Havilland as ‘Kit Carson’ Holliday, meeting George Custer and Jed Stuart on a train ride to Kansas in Santa Fe Trail (1940)
Review:
Massey as John Brown and Van Heflin as Carl Rader, the military man who helps him plan his attacks, are the villains of the piece, but the film is careful to tiptoe around the right and wrong of the abolition movement.
It also plays fast and loose with history, since Custer wasn’t at Harper’s Ferry and there’s no indication that he and Stuart were personal acquaintances. Stuart and Robert E. Lee were among those who helped put down the rebellion, with far fewer lives lost than the film would have you believe.
All that said, this is an action-packed if somewhat oddly titled film. It certainly isn’t about the Santa Fe Trail, though Kit Carson Holliday’s dad dreams of building a railroad west to Santa Fe if he can convince financiers that Kansas is safe enough.
This marked the third Western directed by Curtiz and starring Flynn; it followed Dodge City (1939) and Virginia City (1940). Once again, along for the ride as comic relief are Alan Hale and Guinn Williams as unlikely soldiers.
This also marked the seventh of nine films in which Flynn and de Havilland would star together. The very next year, Flynn was cast of George Custer in the superb “They Died with Their Boots On,” though it’s another film not too concerned with historical accuracy.
Ronald Reagan as George Armstrong Custer, fresh out of West Point and fascinated by ‘Kit Carson’ Holliday in Santa Fe Trail (1940)
Raymond Massey as John Brown, trying to get his message across in Santa Fe Trail (1940)
Directed by:
Michael Curtiz
Cast:
Errol Flynn … Jeb Stuart
Olivia de Havilland … “Kit Carson” Holliday
Raymond Massey … John Brown
Ronald Reagan … George Custer
Alan Hale … Tex Bell
Guinn Williams … Windy Brody
William Lundigan … Bob Holliday
Van Heflin … Carl Rader
Henry O’Neill … Cyrus Holliday
Gene Reynolds … Jason Brown
Alan Baxter .. Oliver Brown
John Litel … Martin
Moroni Olsen … Robert E. Lee
David Bruce … Phil Sheridan
Hobart Cavanaugh … Barber Doyle
Charles D. Brown … Maj. Sumner
Frank Wilcox … James Longstreet
William Marshall … George Pickett
George Haywood … John Hood
Ward Bond … Townley
Russell Simpson … Shubel Morgan
Charles Middleton … Gentry
Erville Anderson … Jefferson Davis
Susan Peters … Charlotte
Runtime: 110 min.
Van Heflin, the abolitionist who alienates many of his West Point classmates in Santa Fe Trail (1940)
Guinn ‘ Big Boy’ Williams as Windy Brody and Alan Hale as Tex Bell, freight line employees who wind up riding with Custer and Stuart in Santa Fe Trail (1940)
Memorable lines:
Carl Rader: “I suppose it takes one of you Southerners to harness a horse.”
Jeb Stuart: “Well, at least we know how to harness them.”
Rader: “You know how to harness negroes, too, I hear — with a strap across their back.”
Jeb Stuart: “What do you do on Saturday night for fun in Kansas?
Kit Carson Holliday: “Well, as I remember, half of Leavenworth takes a bath and the other half gets drunk. And since there are only two bathtubs in town, things get kind of exciting around midnight.”
Cyrus Holliday, offering advice to Custer and Stuart as they prepare to escort a supply train to Santa Fe: “Keep your eyes open and move fast. You’ll like the scenery, but don’t trust it.”
George Custer, as Brown and his men flee: “They’re running! They’re getting away!”
Jeb Stuart: “No they’re not. We’re going after them.”
Custer: “Hey, wait a minute. They outnumber us three to one.”
Stuart: “Well, if it makes you nervous, don’t count ’em.”
Moroni Olsen as Robert E. Lee, considering the appropriate punishment for rambunctious cadets in Santa Fe Trail (1940)
Erville Alderson as Jefferson Davis with his daughter Charlotte (Susan Peters, aka Suzanne Carnahan) in Santa Fe Trail (1940)
Jason Brown, about his father: “He can’t be right, can he Miss?”
Kit Carson Holliday: “I don’t know. His reasons may be right, Jason. They may even be good and great reasons. But what your father is doing is wrong, terribly wrong. And he’ll keep on repeating that wrong as long as he lives.”
Jeb Stuart, trying to get information from the barber in Palmyra: “I hear you’ve got some pretty tough customers here.”
Doyle: “Tough? I’m afraid to shave half of them for fear they’ll get up and cut my throat.”
Tex Bell, trying along with buddy Windy Brody to gain admission to an Army ball: “We ain’t got no invitations, Joe. Can’t we get in on our uniform?”
Joe: “No, sir. Nots unless you wants to go right out on ’em again.”
Windy: “We’re the fellas who cleaned up Kansas. Ain’t you ever heard of us?”
Joe: “Sorry, sir, but we don’t need no cleaning.”
Gene Reynolds as Jason Brown, questioning his father’s descent into lawlessness in Santa Fe Trail (1940)
Alan Baxter as Oliver Brown, trying to smuggle slaves into bloody Kansas in Santa Fe Trail (1940)
Henry O’Neill as Cyrus Holliday, Kit’s dad and owner of a freighting business in Santa Fe Trail (1940)
Ronald Reagan as George Armstrong Custer and Errol Flynn as Jeb Stuart, friends on the battlefield, vying for the same woman off it in Santa Fe Trail (1940)
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