Day 923: The Moderately Bungled Legend Of The Dalton Gang

originally published July 11, 2014

Of course, we all know the stories of Billy the Kid, Wild Bill Hickok and Jesse James, but do we really know… wait, I can’t make that assumption anymore. There have been maybe three or four decent western movies released in the 22 years since The Unforgiven, so it’s a safer guess that our collective knowledge of old west outlaws is probably somewhat shallow, apart from basic name recognition.

So maybe most people only know Jesse James as that West Coast Choppers guy, and maybe there are some who believe Billy the Kid was the character Gene Wilder played in Blazing Saddles. A hundred years ago, anywhere from 10-20% of American movies were westerns; now the genre barely shows up as a blip on the map. But alas, I’m digressing off the dusty path.

If the biggest names of America’s frontier days have already drifted into pop-culture obscurity, then I’m sure the tale of the Dalton Gang is utterly recondite. This is a tale of outlawism, of high aspiration and of ludicrous ineptitude. It’s a story that truly deserves a modern re-telling (and perhaps a resurrection of one of film’s most delicious genres).

It all begins here, with Frank Dalton. Frank was the eldest of 15 kids, a Deputy US Marshal and by all accounts, a hero. He was shot dead in the line of duty while trailing a horse thief through the Oklahoma Territory in 1887, and within three years his brothers (Grat, Bob and Emmett Dalton) had followed in Frank’s footsteps and joined the noble side of law enforcement. After a monetary dispute left the brothers feeling soured on their distinguished vocation, they hopped across the proverbial tracks and became bad guys.

Let’s do a quick sweep of the Dalton Gang that formed in 1890:

  • There were the brothers: Gratton (Grat), the eldest brother who had idolized Frank; Bob, the wild man who murdered a romantic rival while he was still a deputy; and Emmett, the youngest of the bunch. Another brother, Bill, was also an outlaw, but he spent most of his years out in California on his own.
  • George “Bitter Creek” Newcomb, who was too crazy even for Bob to keep in line.
  • Charley Pierce, who was a smooth-talker with the ladies (actually, I have no idea if this is true but at this point I’m looking at casting ideas).
  • Blackfaced Charlie Bryant, who had a permanent black mark on his cheek from a gunpowder incident.
  • Bill Doolin, a great shot and a savvy strategist. Also, he looked enough like Michael Fassbender to get us an A-lister for this movie.
  • The other guys: Dick Broadwell and Bill Power.

After having robbed a gambling house in Silver City, New Mexico, the Dalton Gang was accused of robbing a Southern Pacific Railroad passenger train. Whether or not they did it is irrelevant; Grat was arrested and sentenced to 20 years for the job. While being transferred to prison by train, handcuffed to a guard, Grat made his move. The guard attached to his wrist fell asleep while the other guard on duty had struck up a conversation with some of the other passengers. Grat took the keys from the sleeping guard, unlocked his shackles, then dove head-first through the moving train’s window into the San Joaquin River.

Grat returned to his brothers in the Oklahoma Territory and got back to work. They robbed four trains over the next 14 months. The one in Lilllietta netted the gang about $10,000, but the others only produced chump change and some jewelry. The law was after them though, and they caught up with Blackfaced Charlie in Wichita. After his capture, Charlie grabbed a gun off a railroad worker and shot Marshal Ed Short. Ed fired his weapon at the same time, and both men were killed.

In July of 1892, the gang wandered into the Adair, Oklahoma train station and took what they could find. They then sat down for a smoke, their Winchester rifles laying across their laps. When the train showed up that evening, they backed their wagon up to the express car and unloaded everything inside. The eleven guards on board were all at the back of the train, and though they unloaded 200 bullets at the Dalton Gang, they didn’t score a single hit. Three guards were wounded and a stray bullet killed the town doctor. It was another score for the outlaws.

Bob Dalton, however, wasn’t pleased. His family gang was gaining a reputation, but these guys were close cousins with the Younger Brothers, who – along with Jesse James – had become the most notorious outlaws in the west. Bob wanted to be a legend. He wanted the footsteps of the Dalton Gang to echo through history. So he came up with a plan: they’d rob two banks at the same time, on the same street, in broad daylight. It was to be the heist of the century.

Instead, it was a monumentally stupid miscalculation.

The targets were the First National Bank and the C.M. Condon & Company Bank across the street in Coffeyville, Kansas. The street in front of the bank was being repaired on October 5, 1892, the day of the planned heists, which meant the getaway horses would be tied up a block away. That was the first problem. The next was the Gang’s choice of towns – they were well-known in Coffeyville and their crappy fake beards and mustaches weren’t fooling the townspeople. Then an employee at one bank lied to the robbers and told them their safe was on a 45-minute time-delay. This allowed the citizens outside to get good and armed.

When the Dalton Gang stepped out of the banks to flee, an epic shootout unraveled. Town Marshal Charles Connelly was killed, and three citizens were hit. Grat Dalton, Bob Dalton, Dick Broadwell and Bill Power were all killed, and though he somehow survived, Emmett Dalton was shot 23 times. One of the other gang members – Bill Doolan, Bitter Creek Newcomb or Charley Pierce – had been holding the getaway horses, but whoever it was took off before the angry mob found him. It was a massacre.

The epilogue of the Dalton Gang was brief for most of its members. Bill Doolin formed his own gang, the Wild Bunch, which rose to become the toughest gang of nefarious thieves in the west for a while. He was taken down by a Marshal’s shotgun blast in the summer of 1896. George “Bitter Creek” Newcomb, who was also a member of the Wild Bunch, started a relationship with a 14-year-old girl named Rose. When he and Charley Pierce went to visit Rose on May 2, 1895, her brothers popped out and gunned both outlaws down.

Even Bill Dalton, the brother who never officially joined the Dalton Gang, found his way into Doolin’s crew. He branched out on his own in early 1894, robbed one Texas bank, then found himself tracked down by a posse. Rather than face prison, Bill ran at the posse full-tilt, taking a hail-storm of bullets as a result.

Only young Emmett Dalton lived to tell his side of the tale. After recuperating from his 23 gunshot wounds, Emmett served 14 years of a life sentence before being pardoned. He moved to California and became a successful author and real estate agent, and an occasional actor. He even portrayed himself in the movie adaptation of his book, Beyond The Law.

So while the Dalton Gang rode off into the sunset more as buffoons than criminal masterminds, at least one happy ending came of it. Now tell me that wouldn’t make for a fantastic summer blockbuster.

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