A Fusillade of Bullets at Tomato Springs

Part four in the series continues the saga of the infamous manhunt and gun battle that unfolded near the quiet community of El Toro 100 years ago this month.

Early on the morning of Monday, Dec. 16, 1912, El Toro rancher John Osterman is notified that an armed stranger has assaulted two sisters from the nearby Cook ranch. Now, the outlaw is holed up in the foothills above an area known as Tomato Springs and threatening to kill as many men as possible before he is captured or killed.

The Santa Ana sheriff's office has been notified, and word is spreading among those living in and around Myford (today's Old Town Irvine) as well as outlying El Toro. In the meantime, those who formed the original search party—among them the Cook's hired man, Al Prater—are waiting for the sun to come up so they might find the outlaw and bring him to justice. 

What follows has been drawn from a number of accounts, including a front-page story published by the Los Angeles Times two days after the assault, as well as a 1968 edition of historian James Sleeper's San Joaquin Gazette, dedicated to the infamous attack and subsequent gun battle.

Even as John Osterman rode the short distance down from his ranch at the Whiting lease and turned his horse northward onto Trabuco Road, he could hear gunfire coming from an area about two miles away.

That area was, in the words of late Orange County historian James Sleeper, "a brush-choked gulch" known as Tomato Springs.

According to Sleeper, the springs first had been discovered by "a thirsty friar with the Portola expedition on July 26, 1769." The official Spanish designation? San Pantaleon. Then, "with the coming of the gringos, wild tomatoes were mysteriously found growing at the water hole, and the present, more pronounceable name was applied."


The assailant had fled into the gradually rising slopes, just above above the springs. This was what the initial group of men pursuing the fugitive had learned, after finding his distinctive hobnailed-boot tracks by lantern light.

Had the outlaw continued deeper into the foothills, or was he hiding nearby? In the pitch black of the night, the men realized that, either way, it would be best to regroup at daybreak. 

Four hours later—right around 6 a.m.—the sun began to rise over the dark silhouette of Saddleback Mountain, casting an eerie red glow.

Near the eastern perimeter of James Irvine's sprawling San Joaquin Ranch—later the site of the El Toro Marine Corps Air Station—the farmers and ranchers reconvened and waited. Then word spread that only about an hour ago the very same outlaw had pulled a gun on the cook at the nearby Ed Chambers ranch. After demanding and receiving breakfast, he disappeared back into the darkness, but not before acknowledging "they will be after me, but I’ll kill all of them ... and then go back and kill the girls' folks."


Anger already had been riding high among the men. They were aware that the stranger had tied 13-year-old Jesse Huff to a fence post, then forced her older sister Myrtle, 17, to a haystack behind the barn. Whether the man had accomplished his intent remained a moot point; later, a doctor would assure newspaper reporters that Myrtle "was not injured in the slightest." 

But whatever had transpired, rape—or attempted rape—was a crime that understandably incited outrage, and many of the men had brought ropes. This was noted by a group of newly arrived Santa Ana lawmen who immediately warned all present not to make any attempts at frontier justice should the man be taken alive. 

Not yet on the scene was Santa Ana Sheriff C. E. Ruddock. The previous night—before his office had received word about the Cook ranch assault—he'd been called away to assist the Fullerton marshal in a case involving domestic abuse.

Acting in Ruddock's stead was Robert Squires. Squires, 42, had once served as a member of the Royal Canadian Mounted Police and then as a scout in Montana before moving to Orange County. His correct designation appears to have been Chief Deputy to Sheriff Ruddock, although most accounts refer to him as under-sheriff.


Among the men Squires had brought with him were Deputy Tex Stacey, Constable Calvin E. Jackson and City Marshal Samuel Jernigan. In addition, Deputy Stacey had brought his bloodhound.  

A gun holster had been recovered in the haystack where the stranger had dragged Myrtle the previous night. The holster already had been identified as belonging to the assailant.

Now Stacey’s bloodhound had picked up the scent of the man who'd been carrying the holster. 

Then further confirmation came from a ridge about 100 feet away. "In the clear air of the morning," wrote a Los Angeles Times reporter, "even before they could see the man, his vile curses and yells of defiance rang out."

Squires, Stacey, and the other deputies immediately advanced up the ravine. Suddenly a burst of rifle shots blasted down at them. 

Squires signaled that he’d skirt around the incline and get above the man. Stacey and the others were to distract the outlaw with a frontal attack.

Later Stacey would tell what happened next.

"Bob was quite a distance from me and evidentially came upon the man almost face to face.

"Both opened fire at once, Squires with his revolver and the bandit with a Winchester. The first shots must have found their mark, for I saw Bob pitch forward."

Then he and the two other men received a fusillade of bullets from the ridge. "Stacey, Jackson, and Jernigan pumped lead at the peak," reported the Times. "Jernigan sought to change position. He slipped and fell, and a bullet spat where he had that instant stood."

Stacey, crouched behind a stand of cactus, continued to fire back with his pistol. It was no match for the desperado’s Winchester model ’94, .25.-35.

"I was pumping lead toward him as fast as I could handle my Colt army special," Stacey testified. "I was about 400 yards away when he hit me in the right shoulder. I was unable to handle my gun with my right hand, so I shifted to the left and kept shooting until a bullet sent the weapon spinning."


A bullet had nicked Stacey’s left hand. A second tore through the rim of his hat, and a third went through the lower part of his vest.

"I’m shot," he cried out to the others.

Then everyone heard the desperado mocking the injured man.

"The fellow taunted me to come up to the top and take him," Stacey continued. "But both of my hands were useless."

Stacey would continue to lie prone behind the cactus for more than an hour until he could be retrieved and taken to a hastily set up medical triage. Then he would be transported to Santa Ana for surgery.

In the meantime, gunfire continued to rain down from the ridge. More men were arriving, among them Sheriff Ruddock, John Osterman, and a man identified in accounts only as Robert LeBard.

LeBard may have been one of those who, beginning around 9 a.m., came out in "dozens of automobiles bearing armed men [that] rushed to the place." 

Many of these men were volunteers. But another contingent—that of Company L, the local National Guard unit, and led by Captain Nate Ulm—also was on the way. According to Sleeper, the guards formed at the Armory Hall, "where they donned uniforms and were issued two bandoliers of ammunition per man."


The militia was on the way, but Stacey had yet to be retrieved, and concerns for Squires were mounting. While some were working on the rescue of the former, others planned an attempt to assist the latter. LeBard and two other men would circle above the outlaw while Sheriff Ruddock would follow Jackson and Jernigan to the spot where Squires had fallen.

LeBard and the others succeeded in driving the desperado from his ledge and "the bandit slipped down into the canyon." But his new position was a "deep draw," as the Times described it, "near the bottom of the brush-lined canyon" and facing the ridge where he’d encountered Squires. Once again having the advantage, the outlaw drove Squires' would-be rescuers back with sniper fire. 

Then a strange lull ensued.

Later it was offered the gunman may have been tying up one of his forearms with a handkerchief to stanch the flow of blood. Stacey had testified he’d heard Squires fire five shots before falling, and it was judged likely that one of Squires' shots caused the wound. The injury would have prevented other men from being killed, for Sleeper mentions that by midmorning many of the untrained "posse" were standing up in full view of the gunman.

The silence continued until around 10:30 a.m. At that time Ruddock, Myford blacksmith Willard Culver, Cook farmhand Al Prater, and another man by the name of Harry Tubbs tried once more to reach Squires.

The Times would report that this time, after crawling carefully through the brush, they found Squires "stone dead, with six bullet holes in his body, one through the neck, one through the upper jaw, two through the abdomen, one through the arm, and one through the shoulder."


"Suddenly the bandit opened fire on the four men crouching beside Squires. Prater fell with a hole from his right temple to just above the right eye, from which his brains protruded. Culver was shot through the knee. Culver struggled to the rim out of fire. A brave band rushed to Prater, dragged him through the brush and over the edge of the ridge.

"These men were carried down the west side of the ridge, and to an emergency hospital established under the trees at the Chambers place where Drs. Wehrly, Ball, Gordon, and Burlew and C.S. Kelly, a druggist, were in charge. From there the injured were sent to Santa Ana."

For the next hour, the Times added, occasional shots were fired, yet "the outlaw remained hidden in the gully."

Halfway through that hour, however, additional help arrived.

The militia was now on site, and a new strategy about to be put into action.  

Please return to this site next week for the fifth and final installment of the Tomato Springs shootout.

Nima December 16, 2012 at 03:21 PM
It's nice to read some history about our neighborhood. Thanks!
Janet Whitcomb December 16, 2012 at 09:13 PM
Thank you, Nima. Given what has happened in the past seven days, this wasn’t the easiest story to write and submit. I will file further comment after the final installment.
Charles December 18, 2012 at 12:50 AM
Yes, I too enjoy these articles. There are lots of neat Orange County historical photos on Flickr. Search for Orange County History on Flickr. I will upload a few neat photos.
Janet Whitcomb December 18, 2012 at 06:38 PM
Thanks for the additional photos, Charles. You're right, Flickr is a super resource!


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