In a 1965 book about Detective Allen Pinkerton written by Ornmont, there is an account of the arrest of gang chief John Reno at Seymour, IN, for the Gallatin, MO, burglary of Nov. 17, 1867. The Reno gang was considered the “country’s first great outlaw band.” There were as many as 100 members, and headquarters was at Reno’s Hotel in Seymour.

The Reno Gang controlled Jackson County, IN, since the spring of 1866. The gang included leader John Reno; brothers Frank, William, Simeon and Clinton; and a sister, Laura. The men had fought for the Union but had returned to Seymour by 1863.

During the night of Nov. 17, 1867, the office of the county treasurer in Gallatin, MO, was burglarized and $23,000 was missing. That may not sound like much money now, but this was during a time when a year’s wages were often less than $300. Local men Frank Sparks, Daniel and Silas Smith, and Brandet Clifton were held in Gallatin for knowledge of the crime. But the Pinkertons reported that John Reno was the one who got the money.

John Reno of Seymour, IN, broke into the safe of the treasurer of Daviess County, MO, and made away with $22,065. The Reno Brothers Gang became notorious nationally for the first great American train robbery in America.

The problem was how to arrest Reno and get him out of Seymour, IN, before the gang could help him.

According to Allen Pinkerton, he was asked to help in the capture of Reno. Pinkerton had three secret agents in Seymour to help with the arrest — Robert Winscott, saloon operator; Phil Oates, gambler; and Walter Meara, freight hauler at the railroad station.

A short time before train time (#29 coming west from Cincinnati toward St. Louis), Phil Oates got to talking to John Reno in Winscott’s saloon. Reno considered himself an authority on trains, so Oates made a $20 bet that No. 31 would be the next train into Seymour. Winscott held the money, and about 10 minutes before train time, Winscott accompanied the bettors to the train station. Meara “emerged from the shadows” at the station and joined the three watching for the train.

As No. 29 pulled into the station, Winscott and Oates pulled revolvers on Reno. Allen Pinkerton, with four Daviess County law officers, got off the train and carried Reno, bellowing for help and kicking, aboard the train which quickly pulled out.

By Feb. 4, 1868, John Reno was in the Missouri State Penitentiary, sentenced to 25 years. Frank became the leader of the Reno Gang, but he was lynched along with William and Simeon on Dec. 11, 1868, at New Albany in Floyd County, IN.

None of the money taken from the Daviess County treasurer was returned. But Daviess County officials Capt. John Ballinger and Sheriff and Treasurer Owen McGee had to repay $2,275 to the county for failure to secure some of the money in the county safe. There was some talk about the safe not being locked, since it was opened without damage by the Reno Gang. At any rate, Daviess County soon purchased new safes.

— by David Stark of Gallatin, MO,
published in the Gallatin North Missourian on March 24, 1993

The Reno brothers and members of their gang were arrested countless times at Seymour, IN, after the Civil war but on each occasion they were released without reprisal. On the night of Oct. 6, 1866, they robbed a train of $12,000. Then in December, John Reno led the gang to Missouri where the gang cracked two safes and removed $22,065 from the and the Daviess County treasury.