The expression “double cross” has an intriguing history rooted in betrayal, deception, and the darker corners of human dealings. Today, it commonly refers to a treacherous act in which someone breaks faith with both allies and enemies, often by betraying one side after pretending to support it. Its origins, however, can be traced back to both literal and figurative uses of the word “cross.”
The word cross itself has long carried meanings beyond its religious symbolism. In English slang of the 18th and 19th centuries, cross often referred to dishonesty or cheating. For example, a “cross game” was one rigged in advance, such as a staged boxing match where both fighters agreed on the outcome for financial gain. A “cross” could also describe swindles in gambling, horse racing, or street cons. The idea came from the notion of “crossing” someone—going against them unfairly or deceptively. In contrast, an “honest” contest was sometimes called a “straight” one. Thus, to be on the cross meant to be part of a crooked or fraudulent arrangement.
The term “double cross” emerged when someone who had already engaged in a dishonest scheme betrayed not only their victim but also their supposed partners in crime. The earliest recorded use of the phrase appears in the late 19th century, around the 1830s to 1870s, in reference to gambling and prizefighting. Imagine two boxers agreeing to “throw” a fight for shared profits: one fighter would unexpectedly go back on the arrangement, fighting seriously and winning. This treachery was not only a betrayal of the public but also of the accomplice—hence, a “double cross.”
By the early 20th century, the phrase broadened to describe any act of betrayal that went beyond a single deception. For example, in confidence games, a swindler might set up an elaborate ruse with partners but then abscond with all the money, leaving everyone else fooled. Newspapers of the time frequently reported criminal double crosses, reinforcing the phrase in popular imagination. The expression became particularly widespread in gangster slang during the 1920s and 1930s, when mobsters, bootleggers, and con artists often outwitted one another in pursuit of power and money.
The First World War also played a role in popularising the idea of the “double cross,” albeit in a different sense. During the war, “double agents”—spies who pretended to work for one side while secretly serving the other—were often described as engaging in double-crossing. This gave the phrase a dramatic, espionage-laden flavour that carried through the 20th century, particularly in literature, film, and journalism.
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