Near dawn on June 2, 1899, an engineer from the westbound Union Pacific Overland Flyer No. 1 fired off a telegram from Medicine Bow, Wyoming: 'First Section No. 1 held up a mile west of Wilcox. Express car blown open, mail car damaged. Safe blown open; contents gone….' Immediately following engineer W.R. Jones' report, a dispatch was sent from the Union Pacific Railroad offices in Omaha, Nebraska, offering a '$1,000 reward for each and every one of the train robbers…dead or alive.' Later, the Pacific Express Company, whose safe was robbed, made the same offer, as did the U.S. government. There were six robbers, so at $3,000 per head, the total reward was worth $18,000.

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The Union Pacific Railroad quickly sent the No. 4 — a specially outfitted train kept ready in Laramie, Wyo., containing cars for horses, equipment, food and men — to the robbery site, near Wilcox Station (often called Wilcox). This posse train arrived at the site about 9 a.m., just seven hours after the holdup. Although the Union Pacific had its own detective force, it also brought the Burlington Railroad and the Pinkerton Detective Agency into the chase. These professionals joined with the local posses, one of which even employed bloodhounds. Wyoming's Governor DeForest Richards also dispatched Company C of the state militia. Within 24 hours, nearly 100 possemen were out chasing the train robbers.

The June 2, 1899, Wilcox holdup would become one of the West's most famous train robberies. The Union Pacific Overland Flyer No. 1 had two sections, each pulled by its own locomotive. The first section was flagged down by two men with lanterns at milepost No. 609 at 2:18 that rainy Friday morning. Thinking that a small wooden bridge ahead might have washed out overnight, engineer Jones brought this first section to a screeching stop. The two men, wearing masks, boarded the locomotive and ordered Jones and the fireman, named Dietrick, to pull forward to the bridge and stop again. Dynamite, already tucked under the trestle, was ignited, and Jones was again ordered to pull ahead 'and be quick about it.' When he moved too slowly for the outlaws, one of them clubbed him with a gun butt.

The train had barely cleared the bridge when the explosion came. Although the bridge was not destroyed, the bandits had prevented the train's second section, whose headlight they had seen, from following. They then told engineer Jones to stop the first section so that the passenger cars could be uncoupled. The mail and express cars were what interested them. Following orders, Jones and Dietrick pulled ahead another two miles, where four more outlaws were waiting. Three of the robbers herded the trainmen over to the mail car and ordered clerks Robert Lawson and Burt Bruce to open up. When the clerks did not immediately comply, the door was blown with more dynamite.

Finding very little, the outlaws next ordered the express car messenger, Charles Woodcock, to open the door. He refused. Again the thieves put a match to a couple of sticks of dynamite and easily blew the express car open. Woodcock was badly dazed in the explosion and unable to supply the bandits with the combination to the Pacific Express Co. safe. Therefore, more dynamite was used to blow open the safe. This charge proved a bit heavy, and succeeded in not only opening the safe but also blowing out the sides and the roof of the car.

By 4:15 a.m., the six bandits had gathered unsigned bank notes, cash, 19 scarf pins, 29 gold-plated cuff button pairs and four Elgin watches. The initial estimate claimed a total of $30,000 was taken, but in 1904, then Union Pacific Superintendent W.L. Park wrote that the railroad had actually lost more than $50,000, some of it in gold. The outlaws escaped in a northerly direction, toward the Hole-in-the-Wall, a well-known outlaw enclave in the middle of Wyoming.

Once the bandits had left the scene, the trainmen limped their broken train about 12 miles into Medicine Bow, the next regular stop, where engineer Jones reported the holdup by telegram to Union Pacific officials in Omaha. Jones' telegram concluded: '….We were ordered to pull over bridge just west of Wilcox, and after we passed the bridge the explosion occurred. Can't tell how bad bridge was damaged. No one hurt except Jones; scalp wound, and cut on hand. Jones, Engineer.' A later telegram added that 'the bent of the bridge was shattered' but it was repaired enough for trains to pass.

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