Along with the railroads came train robberies by gangs of outlaws. The most infamous robbery in this area was the hold-up of the Missouri Pacific train at the Otterville Cut in July, 1878, by the James' gang. This gang, headed by Jesse and Frank James, has been the subject of many, many stories in Tipton through the years. One story said local men staged the Otterville robbery with the James gang getting the blame (or credit), as often happened. Another story said that the gang kept their horses in a Tipton livery stable while they planned the train robbery. Also, rumors of local men who rode with the James' abounded. Bob Ford, the man who shot Jesse James, was the brother of a Tipton resident.
Whether or not Tipton citizens played a role in the James' hold-ups will probably never be known for sure, but we do know that Frank James' arrival in Tipton created great excitement as this article from The Tipton Times shows:
As early as Sunday morning it was whispered around town that Sheriff Rogers of Cooper County, Frank James and family were on west-bound train No.1, leaving St. Louis, and would be here at 3:30 p.m. to stay overnight and take the Branch train for Boonville on Monday morning.
The news spread like small pox, and by noon curiosity was on the qin vive, and even the smallest kid in the city was shouting the joyful news that the ex-outlaws was a cummin.'
Soon after noon the crowd began gathering at the depot, and by 3 p.m. it seemed as if every man, woman, child and dog in town had turned out indiscriminately, without regard to age, sex, color or previous condition of servitude, to witness the triumphant entry of the modern Robin Hood of America. When the train pulled in, the interest became intense and the crowd surged wildly to and fro, intoxicated with excitement, vainly endeavoring to spot the long looked-for arrival. Sheriff Rogers and party stepped out of one of the chair cars and went immediately to the Tipton House.
Frank James is a tall, spare built, stoop shouldered man with light complexion and sandy hair. He has the appearance of a man whose health and the strength have been greatly impaired by a life of trouble, exposure and subsequent confinement.
Mrs. James is small of stature with dark hair and eyes, and is a fine looking, intelligent lady. Their little son, ''Bobby", accompanying them, is a fine little fellow, apparently about 7 or 8 years of age.
A Times reporter, through the courtesy of Sheriff Rogers, had the honor of introduction to Col. James, who, although very weary from long travel, was very kind and polite, answering numerous questions with an obliging courtesy. He remarked to the reporter that there were three eventful days during his recent sojourn in Alabama, he would never forget-last Valentine's Day, when he arrived in Huntsville, Ala. The day his wife arrived there and visited him in prison, being the 18th of March, the anniversary of the assassination of his brother Jesse: and lastly, the day Sheriff John Rogers arrived in Alabama, being his own birthday--he was 44 years old on that day.
Sheriff Rogers stated to the reporter that Dick Liddle had got into a bad box. After giving his testimony against Frank James, Dick was arrested for participation in the Mussel Shoals affair, and stood a slim chance of getting clear.
The entire party retired early to rest and took the 6 a.m. Branch train for Boonville, Monday.