John Wesley Penton
(Thank you, Anne Penton Pinckard)
There had been an arrest attempt in 1890, that resulted in the severe beating of two officers from Pensacola, who had made the trip to Milton to capture Penton. Until May of 1891, there had been no further attempts.
In late April, or beginning of May, the Governor of Alabama, Thomas Jones, demanded that Florida extradite Penton back to Alabama. Governor Francis Fleming issued a writ of extradition to all the County Sheriffs in the State of Florida. Sheriff Thomas J. Watts, of Washington County, Florida appointed two special deputies to accompany him to Milton. They were, J. S. Ball, the Chipley Fla. town Marshall, and J. R. Shoemaker, a Chipley businessman.
In Alabama, W. D. Cheatham, an Agent for the State of Alabama from Montgomery, Robert Charlson and D. S. Jackson, both of Birmingham took a train to Pensacola, and then on to Milton, arriving about 4:30 pm. At 5 pm they met the three from Washington County, and a man named Harry Adams from Troy, Alabama.
Following a consultation at the Railroad Depot, Shoemaker, and Adams walked to town to see if they could spot Penton. The remaining five posse members boarded the train as if returning to Pensacola. About a mile or so out of town the conductor slowed the train and the officers jumped off and concealed themselves in the woods waiting for sundown.
After dark, the officers made their way along the track back to the depot, and met Adams and Shoemaker who reported that they had seen Penton in a bar and observed him while having a drink. The officers walked to the town square to see if they could spot Penton. Around 9 pm Cheatham and Adams entered the bar, followed shortly by Charlson and Jackson. The other three officers secreted themselves close by to provide back up.
Shootout in the Streets of Milton
Not seeing Penton in the bar, Charlson and Jackson stepped out of the bar onto the sidewalk out front, followed a few minutes later by Adams. Cheatham was still in the bar speaking to the bartender.
The Street was crowded with people, and across the street a man was selling goods by torchlight. Adams scanned the crowd and spotted Penton in the street talking to another man. He pointed him out as the man with the long beard. Cheatham joined the others on the sidewalk, and they planned their approach.
Cheatham and Adams were going to approach Penton from the front, and Charlson and Jackson were going to make a circuit and approach from the rear, all converging at the same time. As they approached, Penton suddenly started walking toward Adams. Adams called for him to stop, and said he had a warrant for his arrest. The officers began pulling their pistols.
Penton quickly produced his own pistol and fired two shots, one hitting Adams in the shoulder. The officers returned fire, and closed on Penton taking his arms and keeping him between them. The shots Penton fired alerted his friends and they began to fire at the officers. Cheatham and Adams had Penton between them moving him up the street away from the torchlight, while Charlson and Jackson followed them with covering fire. The other three officers joined the fight, one of them having a double-barreled shotgun. The shotgun cleared the street as the officers made their way toward the depot. During the melee, Penton was hit in the back. He screamed, “My God, I’m shot!” and slowly sank down to the ground. The officers commandeered a cart, loaded Penton and hurried to the depot. Penton may have lived about 10 minutes after being wounded.
In the midst of the gunfight, Shoemaker, and Jackson got separated and had been set upon by friends of Penton. They were knocked down, and Jackson’s hand was damaged when someone wrenched his pistol away from him. When they made it to the depot, the other officers were relieved to see them alive. After wiring for a special train, the officers put Penton’s body in the depot, and set up guard while waiting for the train.
The City Marshal of Milton, took the side of Penton and his friends during the fight and immediately after tried to arrest the officers. Sheriff Watts told him there was a warrant and they were legally authorized to make the arrest. When the Marshal persisted a fight ensued and the Marshall was knocked to the ground. He made no further attempt at arrest.
Where was the Santa Rosa County Sheriff?
The Sheriff of Santa Rosa County was William Jackson. During the gunfight he was conspicuously absent. He knew Penton and knew he was wanted in Covington county for fleeing a life sentence. Presumably he had also received the writ of extradition from Gov. Fleming
An inquest was convened in Pensacola and determined that Penton died of gunshot by an unknown person. Nobody knows who fired the shot that killed him. It was determined to be a .45 caliber shot from a pistol from some distance. Penton’s body was returned to his family.
As the officers from Alabama were buying tickets to return to Montgomery, they were arrested without resistance for murder by Santa Rosa County Sheriff Jackson. The officers quickly got an attorney and filed a writ of habeas corpus and were released. They were back in Alabama by Sunday afternoon.
John W. Penton was born in Alabama even though the newspaper claimed North Carolina. During the Civil War he served as a Private in the 1st Florida Regiment. (After his death, his wife Josephine and his children moved back to Andalusia, where she drew his war pension and ran a boarding house.)
In the 1880 census, Penton is shown as a “Retail Grocer”, but by 1884 he had gained some local notoriety when some U. S. Marshalls traveled to Andalusia to arrest some timber “depredators”. The marshalls were attacked by Penton and some friends and ran out of town. He was soon elected Sheriff of Covington County, and was serving his term when he killed Robert E. Crumpler.
Penton Kills an unarmed Man
On June 18, 1888 in the late evening, Sheriff John W. Penton shot and killed Robert E. Crumpler.
Penton tried to collect a fine and court costs in a judgement obtained in Chancery Court against Crumpler. Crumpler had appealed to a higher court and was advised by his attorney not to pay until the court had made a decision.
Just before dark, Crumpler’s two mule team with a wagon of lumber was driven into town by an employee.
Sheriff Penton took possession of the two mules and led them over in front of Prestwood’s Barroom and leaned against a column of the porch, holding the bridle reins. When Crumpler learned of this he went to confront Penton. When he accosted the Sheriff, Penton kicked him hard in the side, and Crumpler staggered away. After gaining control he approached Penton again and Penton shot him in the throat, with the bullet going through the windpipe. Crumpler died later that night. (His headstone shows his date of death as the 19th of June, so it was probably after midnight.)
Penton surrendered to authorities on the 20th, and soon after a coroner’s inquest was held.
From the Montgomery Advertiser dated June 27, 1888:
We the jury, summoned to hold an inquest on the body of R. E. Crumpler, lying dead at the residence of Mrs. Frank Smith, in the town of Andalusia, State of Alabama, upon our oath, after examining all the testimony, state and present that the deceased R. E. Crumpler, came to his death from a pistol shot in the hands of John W. Penton unlawfully on the 18th day of June, 1888 in the town of Andalusia, given under our hands this, the 20th of June, 1888.
H. B. O’Neal
Jno. F. Thomas
J. J. Wiggins
W. B. Baker
P. J. Gantt
On Friday, and Saturday, the 25th, and 26th of June, Judicial proceedings before Justice M. V. Hare, resulted in a verdict of Guilty of First Degree Murder, and Penton was refused bail. The verdict was appealed to Probate Judge Malachi Riley, who rendered his judgement of Second Degree murder, and fixed a bond of $2500, which was paid promptly. (This must have been the indictment because Penton actually went on trial in March of 1889.)
At the Penton trial in March of 1889, Penton was found guilty of Murder in the First Degree and sentenced to life in the state penitentiary. Penton had been forewarned about the verdict and did not show up in court to hear the verdict and could not be located. A reward of $250 was offered for Penton’s arrest and delivery to the Sheriff.
He moved to Milton with his family because he had other family there and was familiar with the area. He lived openly with no attempt at deception and many people including local authorities knew he was a wanted man.
Milton was an exciting and dangerous place at one time. Sheriff Jackson was a one termer and was replaced with the first 4 year stint of Long John Collins. I haven’t found the name of the Milton Town Marshal who tried to arrest the Alabama contingent before they could get out of town.I would like to know where the shootout occurred, but cannot pinpoint it at this time. I’m thinking it might have been on or near Oak street, but that is speculation.
Grave of John W. Penton
Milton, Santa Rosa Co., Florida