The File Inside the Cake: True Tales of Prison Escapes

Jailbirds really have tried to fly the coop by way of contraband—files, handsaws and even guns—hidden inside baked goods

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Along with using bedsheets to fashion a makeshift rope ladder and plying a spoon to dig a tunnel, one of the biggest cliches of prison escape stories involves an inmate receiving a cake with a file inside. The image is so ridiculous that it seems more apropos to Saturday morning cartoons and half-baked movie plots. Right? Well, turns out that real life jailbirds really have tried to fly the coop by way of contraband—files, handsaws and even guns—hidden inside baked goods.

The earliest case I found was recorded in an 1804 compendium of criminal behavior—and it’s an instance of successful use of cake as a means of securing freedom, albeit in a backhanded way. William Blewitt was a gang member known for his pickpocketing prowess and tendencies toward housebreaking. Sentenced to seven years for an undisclosed offense, Blewitt was placed aboard a prison ship where he learned that several felons procured saws and files by way of gingerbread cakes and were planning to escape before the ship set sail. Blewitt alerted the authorities to the plot and was pardoned.

As reported in the January 14, 1909 edition of the Los Angeles Times, Mr. F. J. Humely was jailed for passing a forged check. While incarcerated and awaiting trial, he was sent two cakes—one with chocolate icing, one with white icing. Sheriff Hammel, who intercepted the package, thought the baked goods were unusually heavy and upon investigation found half of a 38-caliber revolver in each cake. Humely apparently planned to wait until only two guards were on duty and either threaten or kill one of them with the gun in order to get the set of keys. The cakes were sent by one of Humely’s friends, a Mr. R. E. Watson, and the pair had planned to sail to Mexico, where they hoped to make money in the opium trade. Humely was ultimately sentenced to seven years at Folsom prison.

Cake facilitated a successful prison break in 1916. Eamon de Valera was imprisoned for his leading role in the 1916 Easter Rising, in which Irish militants revolted against the British government in a failed bid to assert their independence. While incarcerated, he “borrowed” the jail chaplain’s master key, melted the stumps of leftover church candles to make a wax impression and sent the copy to his companions on the outside. They were able to fashion a metal key, which they sent back to de Valera by way of a cake, though unfortunately it didn’t work in the lock. Another key and another cake later, de Valera was able to pass through every gate in the prison and walked off scot-free. De Valera later went on to serve as the third President of Ireland between 1959 and 1973.

There are other success stories to be found; however, the sensationalism of the newspapers, and the fact that the criminals seem to exist only in a single newspaper article, raises red flags in my head. Nevertheless, a fun story is a fun story. I’d take the following with a grain of salt unless there are true crime aficionados out there who can verify any of these cases.

Charlie Howard was serving a sentence for an undisclosed crime and couldn’t wait to marry his sweetheart, May Coyle, who was described in the February 28, 1906 edition of the Washington Post as “eighteen and not bad looking.” (Such flattery!) The warden allowed the marriage to take place, and the new Mrs. Howard had the presence of mind to bring her own wedding cake, decked out with thick, white frosting and decorated with a wedding bell in the center. After serving the cake, the warden and his fellow policemen fell asleep. When they awoke, Mr. and Mrs. Howard were gone, having used steel saws to break through the bars. (Why they didn’t snag the keyring off one of the sleeping guards isn’t explained.)

And then there’s pie. While not the stereotypical smuggling vessel, they’re proven to work—at least if your baking skills are on par with those of Mrs. John C. Wilderman. As reported in January 19, 1914 edition of the Washington Post, her husband was incarcerated in the Middlesex County, New Jersey jail for stealing several miles of trolley wire—a stunt that left a cable car stranded—and she made a habit of bringing him mince pies on a weekly basis. Turns out the jail warden was a pie fiend and on one visit she brought an extra pie especially for him. The warden soon fell asleep. (Noticing a theme here?) When he woke up, he found an empty cell and two discarded hand saws. The article never says outright if the warden was drugged or if the saws were concealed in the pies proper or if Mrs. Wilderman smuggled them in by some other means.

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