March 15, 1881
Two California boys are riding the box on this chilly night along the San Pedro River bottom. Eli “Bud” Philpot, a top-rated stage driver who hails from Calistoga, California (about 60 miles north of San Francisco), and shotgun messenger Bob Paul, all six feet six of him, a former sheriff of Calaveras County (east of Sacramento). They are about halfway to Benson, after leaving Tombstone several hours earlier.
After passing through Contention City, the Kinnear & Co. stage (with a reported $26,000 cargo) rumbles north about two miles. While the stage goes up a small incline, 200 yards short of Drew’s Station, a dark figure steps onto the road from the east side and calls out, “Hold!” Without even a pause, Paul roars back, “I hold for no one!” and shoulders his double-barrel shotgun.
At the same time, more men step out of the brush and both sides fire as one. Hit in the crossfire, a mortally wounded Philpot takes the lines with him as his lifeless body falls “heavily forward between the wheelers” (the two horses closest to the wheels), causing the entire team to “immediately [spring] forward into a dead run.”
Riding atop a careening, driverless stage, Paul answers back shot for shot as angry outlaws step onto the road and empty their rifles at the disappearing stage.
The stage blows by Drew’s Station, where its employees, upon hearing the commotion, come running out. Swallowed up in the darkness and finally out of range, Paul has no choice but to jump down onto the wagon tongue as the stage perilously lurches and bounces toward imminent disaster. He works hard to keep his balance with one hand and capture the flailing, slithering lines with his free hand. After a good mile, Paul grabs enough of the “ribbons” to bring the horses to a stop.
Worried that the road agents might follow on horseback, Paul quickly takes stock of the nine, very shaken passengers and discovers that Peter Roerig, who has been riding on the dickey seat atop the stage, is badly wounded. Paul retakes the box and pushes the team to Benson without further incident. From Benson, Paul sends a telegram back to Tombstone with details and a plea to alert the local authorities (he also includes a statement that Roerig “could not possibly live”).
After dropping off the passengers in Benson, Paul starts back to the scene of the ambush.
Below Drew’s Station, Paul finds the employees with “poor ‘Budd’ [sic] lying dead in the road.” The station agents tell Paul how they came out after the shooting and witnessed “the murderers fleeing rapidly from the place.”
Death on the Benson Stage
After a short stop in Contention City, Bob Paul gets back on the box while Bud Philpot guides the stage north to the next stop, Drew’s Station. On a small rise, just 200 yards short of the station, a masked man steps onto the road and yells, “Hold!” In the ensuing gunfire, Philpot is hit near the heart and topples onto the road. The spooked horses take off for a good mile as Paul jumps down on the wagon tongue—the frontier equivalent of stagecoach surfing—to bring the horses to a stop.
Was Doc Holliday One of the Benson Stage Robbers?
After the Benson stage robbery attempt, lawman Billy Breakenridge says a “common rumor” swept Tombstone that Doc Holliday was in on the robbery. Holliday was tight with Billy Leonard, one of the prime suspects, who he’s known since their gambling days in Las Vegas, New Mexico.
Suspected accomplice Luther King was “an important witness against Holliday,” according to the Tucson Star. Unfortunately, King escaped jail.
The Star later reported the circumstantial evidence against Holliday: “he engaged a horse at a Tombstone livery stable, at about four o’clock, stating he might be gone seven or eight days, and he might return that night, and he picked the best animal in the stable. He left about four o’clock armed with a Henry rifle and a six-shooter. He started toward Charleston, and about a mile below Tombstone cut across to Contention, and when next seen it was between ten and eleven o’clock riding into the livery stable at Tombstone, his horse fagged out. He at once called for another horse, which he hitched in the streets, for some hours, but did not leave town. Statements attributed to him if true, look very bad, indeed, and if proven are most conclusive as to his guilt, either as a principal actor, or an accessory before the act.”
To make matters worse for Holliday, his mistress Kate Elder signed an affidavit admitting his involvement in the robbery attempt (she claimed Holliday had a rope mask in his trunk for a month before Philpot’s killing). On July 6, 1881, Cochise County Sheriff John Behan arrested him.
Holliday was ultimately discharged for lack of evidence, but longtime Earp ally Fred Dodge always believed he was involved in the robbery, saying, “Doc was a tough citizen and a bad egg. Doc never played square with any one in that country. Bill Leonard was as hard as nails and was a stage robber and everything else in the line of crime. Doc was a full fledged member of the gang that Leonard was in with.”
Embarrassed by an unwanted association with outlaws, Wyatt Earp dismissed the accusations, saying his friend wasn’t a thief and wasn’t “in any way connected with the attempted stage robbery,” adding, “For three-quarters of an hour after the stage passed the Wells, two and a half miles from Tombstone, he was seen at the latter place, so drunk that he was helped upon his horse, and the robbery occurred thirteen miles from Tombstone so it was utterly impossible for him to be there.”
According to folklore, Holliday replied to the accusations with: “If I had pulled the job, I’d have got the  thousand.”
While the former dentist had a nasty streak and a strange set of friends, the evidence against him is circumstantial, and it’s about an even split as to his involvement. It’s not hard to imagine that Holliday may’ve intended to go on the raid but got too drunk to show up.
Close Call for Paul
A most terrible affair of last evening. First intimation I had of it was when Doc. [George] Goodfellow burst into room and asked for rifle. [Grafton] Abbott finally let him have his upon Doc’s assurance he didn’t want to kill any one. I stopped our chess, got revolver and followed him up, not wishing him to get hurt if I could help it. Men and horses were flying about in different directions, and I soon ascertained the cause. A large posse started in pursuit—$26,000 specie [coin] reported on stage. Bob Paul went as shot gun messenger [guard] and emptied both barrels of his gun at the robbers, probably wounding one. “I hold for no one” he said and let drive. Some 20 shots fired—close call for Paul. Capt Colby wished me to form [be] one of another posse, to head the robbers off at San Simon if we could get necessary information upon arrival of stage, and we worked the thing up. Got rifles and horses, and I got [John] Clum (mayor) and Abbott to go with us. Probably six in all. Information didn’t come as we expected, so delayed, and several of us shadowed several desperate characters in town, one known as an ex-stage robber. Couldn’t fix anything. Bud Philpot, the driver, was shot almost through the heart and the passenger, a miner [Peter Roerig], through the back. Doc showed me the bullet that killed him—an ugly .45 calibre. Some more tracking tonight. Our birds have flown.
Parsons’ entry for March 28:
[Luther] King, the stage robber, escaped tonight early from H. [Harry] Woods [Sheriff John Behan’s undersheriff] who had been previously notified of an attempt at release to be made. Some of our officials should be hanged. They’re a bad lot.
Aftermath: Odds & Ends
At daybreak, Sheriff John Behan led a large posse, which included Wyatt, Virgil and Morgan Earp, Bob Paul, Bat Masterson, scout Buckskin Frank Leslie and others, that trailed the highwaymen toward the Dragoon Mountains and then back to the San Pedro River. At Redfield’s ranch, the lawmen flushed out Luther King, who squealed on the stage robbers: Billy Leonard, Harry Head and Jim Crane.
Behan took the prisoner back to Tombstone, while the Earps and others continued the pursuit, tracking the desperados up over Redington Pass and clear around the Rincon Mountains. After a rendezvous in the Dragoons, Wyatt and Masterson “hoofed it” back to Tombstone, while Virgil and others trailed the brigands all the way to Cloverdale, New Mexico, without success. The officers logged almost 400 miles in the saddle. But the outlaws didn’t have long to run, for all three suspects came to violent ends in the next several months.
Wyatt got a double load of bad news when he returned to Tombstone. He found out Behan had appointed Harry Woods as his undersheriff (Earp was led to believe he would get the nod). Based on rumors of a cow-boy-led jailbreak, Wells Fargo detective Jim Hume and Wyatt requested that Luther King be put in irons. Fifteen minutes later, King simply walked out of the jail and escaped on a horse tied out back (see Parsons’ entry at left).
Recommended: “Robert Havlin Paul, Frontier Lawman” by Roy B. Young, published in Western Outlaw-Lawman History Association Journal, Fall 2004.