A Freight Train Ride and a Return to Jail

How the story began — The Stage Robbery at Kane Springs Canyon

What happened next — Pearl Hart and Joe Boot Captured Near Benson

Pearl Hart had made it through the hole in the wall and out of the Tucson courthouse. Ed Hogan, the jail trusty suspected of helping her escape, was gone too.

Now they had to get out of town.

According to the Tucson Citizen’s October 21, 1899, account of their recapture, Pearl and Hogan went to the depot and found a freight train about to leave. They hid between two cars and rode east out of Tucson in the early hours of October 12, 1899.

For a little while, their plan worked.

But at the train’s first stop, the crew discovered its two extra passengers and put them off.

The freight had offered a quick way out of town. Once the crew put them off, that part of their plan was over. The next decision was whether to stay together or take their chances separately.

The account doesn’t name the stop. Wherever it was, Pearl and Hogan were back on the ground, with the railroad no longer carrying them away from the jail they had just escaped.

They decided to separate.

The newspaper suggested they thought they would have a better chance traveling alone. Both left the railroad and headed into the country on foot, going in different directions.

Before parting, though, they reportedly made an arrangement to meet again.

For the moment, they would travel separately. But their escape still depended on finding one another again.

Back in Tucson, people were trying to work out where Pearl had gone. There was no shortage of ideas.

One early report suggested horses had been waiting and that the fugitives had headed straight for the Mexican border. There was also a story about a heavily veiled woman boarding a westbound passenger train.

The writer of “Free Again” doubted the train story, reasoning that Pearl would have difficulty disguising herself from anyone who knew her.

By late that night, another report was circulating: Pearl had been caught alone and on foot on the road between Tucson and Florence.

The jail officials knew nothing about that supposed capture.

A few days later, the Tombstone Epitaph passed along word that she had been caught near Nogales while trying to cross into Mexico. Even that little notice described it as a report making the rounds.

People had Pearl heading west, north toward Florence, and south toward Mexico.

The later account of her recapture put her on an eastbound freight.

While those stories were circulating, Sheriff Wakefield was out looking for the two missing prisoners.

He started after them the day following their escape. According to the newspaper, he had little difficulty picking up Pearl’s trail.

Hogan was another matter. His trail was lost.

Now, this is where the account takes an interesting turn.

The paper claimed that, from the second day after Pearl’s escape, Wakefield knew where she was. Either he was watching her himself or another officer was doing it for him.

But he didn’t bring her in.

Wakefield wanted Hogan, too.

Finding Pearl solved only half the sheriff’s problem. Hogan had disappeared from the jail the same night, and officials suspected him of cutting the opening that let her out. Bringing Pearl back alone would still leave the suspected helper at large.

He didn’t know where Hogan had gone, but he believed the two had agreed to meet somewhere. If he arrested Pearl right away, he might lose his best chance of finding the man suspected of helping her out of jail.

So, according to the account, he let her keep going.

Pearl thought she was making her escape. Wakefield was waiting to see who would turn up beside her.

The newspaper called the eventual recapture a feather in Wakefield’s cap. In its telling, the sheriff had turned a search for two scattered fugitives into a waiting game.

At one point, Wakefield was reportedly near her without her realizing he was there. Then he learned that she was heading for Deming, New Mexico.

There was no need to follow her all the way himself if he could put someone at the other end.

Wakefield telegraphed Deputy Sheriff George A. Scarborough in Deming. Pearl Hart was coming his way, he told him. Keep her under observation.

And wait.

Scarborough was instructed not to arrest Pearl unless Hogan appeared. If Hogan joined her, he was to take them both.

That instruction was the heart of the arrangement. Pearl’s arrival by itself wasn’t the signal to move. Scarborough was to give her enough room to meet Hogan, then end the escape with both of them in custody.

Wakefield also offered him fifty dollars for his trouble.

With that arranged, Wakefield returned home. Pearl continued toward Deming, apparently unaware that an officer there had been told to expect her.

The account leaves much of the journey unexplained. It follows Pearl closely enough to put her in Deming, but gives us no such trail for Hogan.

Once there, she entered what the paper called a “house of ill fame.”

She had been in the house a day and a night when Hogan arrived.

For that day and night, the two fugitives were still apart. Then Hogan came to the very place where Pearl was staying. The rendezvous Wakefield had been counting on had finally happened.

As soon as Hogan appeared, the deputy arrested them both.

After the hole in the courthouse wall, the freight train, and the days traveling separately, their reunion in Deming ended with an officer taking them into custody.

They were brought back to Tucson by train and returned to the county jail.

Hogan had been only days from completing his sixty-day sentence when he disappeared. He could have finished his time and walked out a free man.

The first escape report put his remaining time at ten days. That is what makes his part in this so striking. Pearl was waiting to answer for a stage robbery; Hogan was nearly finished with a short sentence for being drunk and disorderly. Yet he left with her, and the two ended up being brought back together.

Instead, he was back behind bars with Pearl, facing the consequences of an escape that had taken them as far as Deming.

For Pearl, the return meant picking up where she had left off. The stage robbery charge hadn’t gone away while she was traveling through the country. Joe Boot remained in custody, and the trial was still ahead.

She had managed to get out of the courthouse.

Staying out had proved a good deal harder.

How the story began — The Stage Robbery at Kane Springs Canyon

What happened next — Pearl Hart and Joe Boot Captured Near Benson

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Sources

“Free Again” — newspaper identification and date pending.

Tombstone Epitaph, October 15, 1899, p. 1.

Tucson Citizen, October 21, 1899, p. 4, “Both Are Caught.”