AMBUSH AT CHOKOLOSKEE: The Murder of E. J. Watson

by Karen Yvonne Hamilton, 2025

This is an excerpt from Lostmans Heritage: Pioneers in the Florida Everglades

Murder seemed to follow Edgar J. Watson wherever he went. He is reported to have killed the legendary Belle Starr and scores of others. Rumor has it that he killed off the workers he hired rather than pay them. After settling on Chatham Bend, a perfect hideaway for criminals on the run, Watson set about creating a plantation that became quite prosperous for that region.

He had plenty of ideas for expansion and building his own little empire down in the Everglades, and many of the residents there did business with him regularly. Family stories tell how many a time Watson sat down to dinner with the Hamilton brothers. While not exactly friends with anyone, descendants of the Hamilton’s report that their ancestors told them that Watson was a likeable man and friendly to most.

Until late October in 1910.

Three of the locals, a man named A. Waller, another called Dutchy Reynolds, and a woman named Ellen Smith, were found floating dead in the swamp. One story claimed that they worked for Watson and he owed them a large sum of money. A black man, Sip Wilson, working with Watson told authorities that Watson ordered he and Leslie Cox, another wanted desperado who was often with Watson, to kill the three. Authorities searched for Cox but didn’t find him. Watson maintained that he had nothing to do with the murders and he would personally find Cox and take care of him. One account says that he returned to the plantation, found Cox there, and killed him. He offered Cox’s hat and coat as proof, but he refused to show anyone where Cox’s body was buried. At that point, the people of Chokoloskee had had enough.

While the October hurricane of 1910 did much less damage than was expected, it still left the residents of the islands rattled and in need of replenishing their supplies. Everyone’s nerves were on edge, from the storm and from the murders that followed in the storm’s wake. On Wood Key, King Gene’s clan was struck hard. The farm destroyed, supplies washed away, housing badly damaged, the family would be forced to move further south to Lostmans for a time. In the meantime, according to one family story, Gene Hamilton made his way north through storm debris to Chokoloskee to get supplies that were ruined in the hurricane.

Along the slow path littered with debris and rotting fish, Gene encountered Ed Watson who was on his way to Smallwood’s Store to tell the men there that he had taken care of Cox. Gene told Watson that the men of the islands had had enough, and trouble was coming. Watson continued on his way anyway. Gene Hamilton watched events unfold from the shore, but according to him, he did not participate in the posse. Gene’s version of what happened that day are consistent with the version most told in the years to come. Watson pulled his gun, but it misfired, and the men opened fire.

Where was the rest of the Hamilton clan when Watson was gun downed in front of Smallwood’s store? Richard’s eldest daughter, Mary married Henry Short in 1901. She was 13 years old. With the exception of Short and Gene, there were no Hamiltons near the shore that day that we know of. Again, the stories passed down through the generations can be taken as absolute eyewitness accounts or not. Already outcasts in a society of outcasts and adventurers, it is likely that the Hamilton family wanted no part of outright murder. The one black man that was present, Short, took the title of ‘first shooter’ for all the generations to come. As far as we know, the Hamiltons had no trouble with their neighbor, Ed Watson.

Some are convinced that there was only one bullet that felled the fearsome Edgar J. Watson. They believe that the only shot fired was the one by Henry Short, who had been chosen by the residents of the area because he was such a good shot. The general consensus goes with the story that Short fired the first shot, and the rest followed suit. The story continues that Watson’s body was later dug out of the water in order to count the bullet holes in his body, which by that time was impossible to do.

It is impossible to know who fired the first shot or who fired the kill shot, but local legend continues to place it on the shoulders of Henry Short. Perhaps the rest of the Hamilton family collectively decided there was no sense in getting white fingers pointing at them when the deed was done. Did they even know what was planned for that day? Rumors travel quickly in a small community, but the Hamiltons were not exactly part of the community. And word did not reach Watson either. He knew the air was unsettled, and he no doubt had his guard up, but did he realize that he was gliding his boat into an ambush? Also, the Hamiltons – Richard, Gene, Walter, Leon, and the rest were friends with Watson. Well, as friendly as was possible with a man like Watson. Perhaps they knew of the ambush and wanted no part of it for that reason.

The one eyewitness to what really happened at Chatham Bend days before Watson was gunned down disappeared. Sip Wilson, identified in almost every account of the Watson murder as simply “the Negro” or “the Nigger,” was paid by authorities to leave town. So the story goes.

Tales in the Ten Thousand Islands tend to shift and take strange turns depending on who is doing the telling. Sip Wilson ended up somewhere in South Carolina for the remainder of his days, no doubt trying hard to put the Florida Everglades far behind him.

As it is with most events of the past, and especially in those islands, we cannot know the true story. We create the possibilities, we mull over the many theories, and we each choose our own version of the truth. Or we simply accept that some things will just remain a mystery forever.

Sometimes the mystery is more exciting than the truth.

Want to read Lostmans Heritage RIGHT NOW?

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Need help writing your family history or memoir? You can contact me at kyvonnehamilton@gmail.com for a FREE consultation.

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Read more about Ed Watson’s murder in this article by Coastal Breeze News (2020). The Story of Edgar J. Watson: The Infamous Businessman & Serial Killer