Fleeing across borders was a fairly typical practice for political dissidents all across the world in the early 20th-century. This was made possible (often even trivial) by a few key differences from our modern day, mostly regarding the reach and penetration of state governments. In particular, borders were not so rigidly policed and personal identities not so well defined by documentation. This means that people were less likely to be caught crossing, and far harder to locate once they did cross. Not that many governments tried particularly hard to track down their dissidents in exile - states just wanted the dissidents out, prosecution was a fairly secondary concern. On the dissident's side, they were able to readily move across borders due to a well-developed, transnational network of dissidents which could offer aid (both direct and indirect) and/or a place of refuge.

A few brief examples taken from the Directory of Individuals in the first volume of Emma Goldman: A Documentary History of the American Years subtitled Made for America, 1890-1901:

"Isaak, Abe (1856-1937) Russian-born American anarchist, editor. Raised in a Mennonite colony, Isaak moved to Odessa as a young man, joining the movement against the tsar. To avoid arrest he fled first to South America and then the United States with his wife, Mary Dyck Isaak." (pg 536) A fairly typical example, which highlights how most dissidents who fled across borders, fled across multiple borders before settling down, usually doing so in an already-established community of radicals and/or other political exiles.

"Kitz, Frank (born Francis Kitz Platt) (1849-1921) English anarchist, Kitz was a member of radical working-class clubs in the 1870s... Fluent in German, he had strong ties to German exiles in London and served as secretary of the Freiheit Defense Committee... while Johann Most was in prison between 1881 and 1882." (pg 538). This example just helps to show how communities of exiles were not uncommon, nor were they disconnected from their place of exile. Quite the opposite, they would often immediately resume their subversive activities upon arrival; though, this example more shows how exiles interacted and formed alliances with native-born citizens.

"Lavrov, Peter L. (1823-1900) Russian populist, writer, philosopher, and mathematician. Lavrov was convicted of treason in 1866 and exiled to Vologda, escaping to western Europe in 1870. Influential in revolutionary circles in and outside of Russia..." (pg 539). Another example from Russia displaying radical's ability to escape from imprisonment/persecution and head immediately towards a location where they can pick right back up wherever they left off.

As to encountering border patrols, the still-developing nationally/internationally standardized system of identity documentation (that is, passports) often left much of immigration control up to the discretion of individual officers. It really doesn't matter how much of a wanted criminal someone is if the person who has "caught" them doesn't actually know that they are wanted. Systems of rigid border control only really started coming together when state's started requiring the presentation of documents verifying one's identity upon entry. Well, somewhat - the history of border control is its own long and complex topic, but what matters to this question is that this control was simply not developed enough to keep close enough track of individuals to be able to stop many wanted criminals from crossing even if they are caught crossing.

In his memoirs, the Lithuanian (then Russian) born immigrant Isadore Wisotsky recounts an encounter he had at the U.S.-Mexican border while returning from a trip to Tijuana in the mid-1920s. Crossing the border into Mexico was no problem, but returning back Isadore traveled with "real smugglers of whiskey and immigrants." Caught by border patrol, Isadore and the smugglers were let free because one of the the patrolmen was raised in the same New York City community as Isadore - "He is my landsman. He comes from the same neighborhood I do." (From pg 218 in the Isadore Wisotsky Papers at the Tamiment Library and Robert F. Wagner Labor Archives in Bobst Library in New York City.)

Carlo Tresca - an Italian-born, unlabled leftist and immigrant who worked closely with the Industrial Workers of the World in the 1910s, well-known for his impassioned speeches to Italian strikers across the country - has a rather hilarious story of an encounter with border patrol upon returning from Canada. As recounted by Max Nomad in his biography of Tresca, upon returning to Michigan Tresca was confronted by a tribunal which essentially gave Tresca an informal citizenship test, asking mostly about occupation and how long Tresca intended to stay. Carlo Tresca - not identifying himself as the political dissident and non-naturalized immigrant Carlo Tresca - claimed to work as a teacher, prompting the following:

"In case you decide to remain in Detroit, do you intend to become an American citizen?"

"This is the great ambition of my life"

"I hope you like Detroit and remain there, because we need citizens like you in this country."

(From page 204 of the Max Nomad Papers, also located at the Tamiment library and Robert F. Wagner archives).

I think that this is enough to get a sketch of the picture across, though there are a few more examples which offer much better illustrations that I'll provide once I get the chance. This entire answer is, of course, tangential to your question of actual criminals (as opposed to political dissidents which I feel we can generally agree are only criminals inasmuch as they openly oppose established authorities) attempting to flee across borders from arrest and prosecution, but I would argue that as long as said criminals had a plan for how they would flee and where they would flee to, these same general rules would apply. But on that specific argument, I have nothing to offer as evidence.

Some sources not already mentioned that I don't have with me at the moment to explicate on their relevance:

Zimmer, Kenyon. Immigrants Against the State: Yiddish and Italian Anarchism in America. Urbana, Chicago, and Springfield: University of Illinois Press, 2015.

Cannistraro, Philip and Gerald Meyer, eds. The Lost World of Italian-American Radicalism: Politics, Labor, and Culture. Westport, Connecticut, London: Praeger, 2003.

Debouzy, Marianne, ed. In the Shadow of the Statue of Liberty: Immigrants, Workers, and Citizens in the American Republic, 1880-1920. Urbana and Chicago: University of Illinois Press, 1992.

Salerno, Salvatore. Red November Black November: Culture and Community in the Industrial Workers of the World. New York: State University of New York Press, 1989.

This last one, in particular, really emphasizes how these were global networks aiding in the movement and resettlement of radicals across borders: Inouye, Daniel H. "A Transnational Embrace: Issei Radicalism in 1920s New York". Journal for the Study of Radicalism, Vol. 12, No. 1, 2018, pp. 55-96.

Border crossings are one of the most treasured motifs from westerns and crime stories. The idea that you could leave your crimes behind by crossing some imaginary line was and is a compelling one. Fleeing the country to avoid the authorities is an idea that occurs in many places throughout history. Criminals, refugees, and political dissidents have all chosen to leave a country rather than face the consequences of staying. The concept itself, however, raises some important historical questions. The creation of national boundaries and enforcing control of those boundaries was a process that occurred in the US over the long nineteenth century.

In the US there has been a long conflict of interests when it comes to border control. Border control is essential to the authority of the state. After all, the government has to have clearly defined spaces where its authority reaches and where it does not. To have crime you have to have law and that law has to have its own space. However, the desire for national control is oftentimes at odds in a nation that has been consistently devoted to the principles of free market trade. Americans typically don’t like it when their ability to make a profit is hampered.

We could go back to the colonial era and explore the rampant piracy and smuggling that American’s engaged in. The thirteen colonies were able to take advantage of salutary neglect to ignore international boundaries in the name of profit. American ships were some of the finest in the Atlantic and American sailors were keen to exploit foreign markets, especially in the Caribbean. Smuggling was particularly lucrative, but piracy is the more dramatic example. American pirates in the New England and middle colonies regularly broke the law, oftentimes in broad daylight. Piracy in the thirteen colonies was an accepted and understood way of bringing profit into the colonies. One colonial governor said that it was a shame that he was supposed to hang pirates whose only real “crime” was bringing gold into the colony. In one notable instance, when local authorities arrested a professed pirate, a mob formed outside the jail and set him free. Which brings the primary problem to the fore. How can the government enforce their authority if the people are not willing to go along with it?

This ambivalence towards the law persisted into the nineteenth century as well. As Americans expanded westward, the problem of international trade and national authority travelled with it. Along the ever-expanding frontier, the illegal whiskey trade flourished as whiskey served as a de facto currency. In the nebulous back country, the fact that this trade was illegal mattered very little and the government had no on the ground agents to establish authority. Consequently, other crimes went unregulated as well. Murder, trading in slaves, and counterfeiting were rampant across the Canadian border in the early 1800s. Counterfeiters and other criminals maintained bases in Canada even though their businesses operated in the Americas. The constant cash shortage in the backcountry meant that these men were tolerated, if not openly accepted, by local communities. Criminals could easily cross borders, but the deeper reality was that they did not necessarily need to cross borders to live like free men.

At sea the situation was even more nebulous, as no one nation could claim ownership of an entire ocean. In the Atlantic, the role of policing the Sea was taken up by the British, especially in eliminating the salve trade. In this instance, there was no border to cross, but slave smugglers preferred flying American flags as the US did not allow the British to board US flagged ships. Along the Gulf Coast, the famous Lafite brothers were actively involved in slave smuggling, along with Texas hero Jim Bowie. Their scheme involved bringing slave coffles across the border and then allowing the authorities to “capture” them. The slaves would then be auctioned off, which would allow the smugglers to repurchase them at a bargain price. This flagrant abuse of national authority did eventually catch up with Jean Lafite, when the Navy was sent to destroy his base on Galveston island. Tellingly, when teh Navy did arrive they allowed Lafite and his pirates to leave peacefully, without even trying to assert national authority over the famous criminal. Jean Lafite then began his final phase of piracy along the Mexican coast, crossing the border to escape his crimes. Of course, he soon died afterwards, but that is neither here nor there.

In the southwest, the Mexican government created the “zona libre” along the border of Mexico. This was a free trade zone designed to help Mexican merchants compete with Americans. This naturally became a hot zone as American politicians frequently lamented both the economic damage the Zona Libre did and its capacity as a haven for criminals. Cattle rustling was especially lamented since cattle move themselves and don’t pay any attention to borders. Even more than cattle, Texas slave owners claimed that the lack of border control meant that their slave could frequently run across the border to freedom. In this case, committing a crime, i.e. running away, was possible only because of the existence of the border.

Blockade runners during the Civil War travelled to Matamoras or Brownsville to bring war supplies to support the Confederate cause. Steam ships turned Matamoras into a boom town, complete with a powerful wartime economy. The lack of border control meant that it was easy to travel across the Rio Grande and into the Confederate interior of Texas. Even after the Civil War, Gilded Age Texans made some ludicrous profits by gun running into Diaz’s Mexico.

Other crimes were absolutely plentiful, and criminals were well aware that they could find freedom by leaving the country. Murderers and thieves aplenty made their living along the Mexico-US frontier. The possibility of freedom and continued criminality was somewhat leavened by the people themselves. Mob rule in both the US and Mexico served as an informal warning that crime could only go so far, regardless of which side of the border that crime was committed on. Lynching and other means of informal justice were an accepted practice in keeping social order along the unclear boundaries between nations. In a few instances, the would be criminals were captured on the opposite side of the border and marched right back to be handed over to the proper authorities.

This nebulous borderland could not last forever, though it persisted in places for much of the nineteenth century. After the Civil War, American law makers began rebuilding the nation, and that included a much greater degree of national authority. Over the course of two decades, roughly from 1877 to 1898, the US made seventeen different extradition treaties with other nations, especially with Mexico. To control the nebulous borderlands was an international endeavor that the US could not do alone. It required cooperation from other nations by necessity. These treaties were not always equitable, as the US was still looking to gain economic advantages, but the growing power of the US meant that it had the advantage at the bargaining table.

Sources: Margolies, Spaces of Law. Andreas, Smuggler Nation. Hart, Empire and Revolution. May, Manifest Destiny’s Underworld.

Edit: counter fitters to counterfeiters. No disrespect meant toward kitchen measurers.

I can answer this question in one very particular instance: fleeing to Canada became a very successful way to avoid being charged with war crimes, or crimes against humanity, in the wake of WWII.

In 2014, Jennifer Hough wrote an article detailing how Canada became an unintended haven for ex-Nazis because of the decision to embrace a policy of moving on from the war without a robust desire to prosecute the Nazis for purpose of deterring future fascists. Lowest estimates place 2,000 Nazi criminals that ran to Canada. There may have been as many as 5,000. In the 90s Canada announced that they would no longer even consider actively looking for ex-Nazis to prosecute. It wasn’t a large change in policy, as a successful prosecution or extradition was very rare.

In this article from the Scholarly Common Law journal it’s noted that by 1962 Canada’s will to investigate WWII criminals had become all but non-existent. The government would only extradite to a limited number of countries (because of treaties) but they also wouldn’t take up prosecution themselves. There was not a legal precedent that covered the enormity of the Holocaust, how many people were involved, the blurring of lines between martial and civilian life, or how many years it might take to investigate the breadth of the crimes. The Canadian law against genocide could not be taken up retroactively. Additionally, “there…was a question whether acts such as the deportation of civilians for purposes of slave labor, would fall within the purview of military law.”

In the final analysis, the Commission concluded that even the pursuit of war criminals could not justify “subjecting citizens to the jurisdiction of military courts, thereby compromising the fundamental values of Canadian jurisprudence.” No section of the Canadian government would cover the case. It took until 1985 to get meaningful codification and statutes in place. By this time many of the criminals were over age 60, which then triggered another argument regarding the practicality and fairness of starting prosecution against someone who is alleged to have committed a crime in another country, under military supervision or not, over 40 years prior.

Former Justice Minister Irwin Cotler said in an interview last October that he was calling for a panel to investigate how Canada has been a haven for war criminals and the only way to correct that was to streamline legal proceedings to make sure war criminals are prosecuted before money set aside (public interest in the case) can be dispersed into other things. Cotler’s opposition say there have been 27 cases against WWII era defendants in the last 40 years and only 10 ended with revocation of citizenship; the time has come to make sure war criminals from more recent conflicts aren’t using Canadian citizenship to hide their crimes.

Canada is currently working on a single case from the war. Helmut Oberlander was 97 years old, claimed he cannot remember even the name of his unit, and anyway he was only an interpreter against his will as he was conscripted. The Washington Post reported that there is supposed to be a resolution soon, but he was deaf, at risk of catching Covid, and he’d had his citizenship revoked so short of sending him back to Germany there’s nothing more to be done. In the end…it was all for nothing, because he died.

I’ll be watching the wrap up and aftermath of Oberlander’s case with great interest. I have to believe he’s the final case the Canadian government will prosecute. Hopefully they’ll continue to address the legal and social policies that let thousands of Nazis evade justice.

Edited to clarify Oberlander died towards the very end of the legal wrangling over his case.

The story of Butch Cassidy and the Sundance Kid escaping to South America and eventually getting caught partially answers the question on getting away with crimes and when it stopped. As these are big names, the story of their escape may have helped support the creation of this troupe. Also consider that there’s been a few movies and books written about these two to help seed the troupe.

Cassidy and Kid, along with their gang the Wild Bunch, had gotten away with a number of robberies in the late 19th/early 20th century. After robbing the Union Pacific Overland Flyer, a massive manhunt was started for the gang. Later shootouts further increased the desire to capture Cassidy and Kid.

This is when detective agencies, like Pinkerton, are coming into their own and filling the niche of recovering stolen goods, which would also make rail seem safer. Pinkerton started better utilizing communication/technology to systematically find robbers. For example, photographs could be reproduced in newspapers and thus increase visibility of who authorities are looking for. The novelty of photography was alluring to people from all walks of life, including Cassidy.

They were trying to legitimatize their work and build their business, so they were more willing to keep at it to capture some big names like Cassidy and Kid. The gang broke up in part because of the pressure of possibly being caught.

Cassidy and Kid realized their time may be up and sought to escape to South America. As some of the other posters have mentioned, there wasn’t a good way to check identities. This meant it was easy to move and change one’s name. The amount of names that were changed (whether or purpose or by accident) at ports illustrate this point.

In 1901, Cassidy and Kid moved to South America in part because it resembled the American West decades prior. For several years, the two laid low with their new names, but they held up a bank in 1905. They were again committing crimes. The difference is that the investigation and capturing techniques that took decades to develop in the American West took less than ten to be implemented in South America. These techniques were far from perfect, though the possibility of disappearing was decreasing drastically and it took much more effort to be successful.

There are many times in the Canadian West when the border was used to flee or avoid persecution from crimes committed.

In 1871 trading liquor with the natives was a crime in Missouri. One day US Marshal Charles Hard learned that a group of men had left Fort Benton with a quantity of alcohol which they intended to trade with the Indians. He set out to arrest the men and demanded they return to Fort Benton when he finally caught up to them. These men boldly informed Marshal Hard that they were 2 miles over the Canadian border where he had no jurisdiction over them. Best returned empty handed and Dutch Fred' Wachter, W. McLean, Mr. Juneau and John 'Liver-eating' Johnson carried on with their journey. When they reached their destination they built a trading post and named it Fort Stand-Off to memorialize their encounter.

The first Canadian federal police force was created in 1873 and was given the task to end the wholesale slaughter happening to and among the Plains Indians and stop the whiskey trade between American traders and Canadian Indians. Fort Whoop-Up was the primary trading post in the Western Canadian Prairies so became the Northwest Mounted Police forces first objective. When the column of NWMP arrived at Whoop-Up they found only David Akers, the double leg amputee who owned the establishment and two of his servants. All of the other occupants and traders had gathered their booze and returned to the safety of the United States before the NWMP arrived.

In 1875 the NWMP were informed of a India who was murdered by a white man in Southern Alberta. They soon learned the location and identity of the culprit and followed him across the border to Fort Benton where they tried to arrest him. When they got to the US Marshall's office in Benton they were informed that killing an Indian was not a crime in the United States so the American Government would not give the Mounties permission to extradite the man across the border to face trial.

In 1876 three different bands of American Sioux were being hunted by the US Cavalry in the aftermath of Custer's destruction at Little Bighorn. While troops of soldiers were hunting these Indians the Mounties earned the respect of citizens in Fort Benton because they were looking for the Indians in groups of two and three. When the first band of 500 warriors and 1400 women and children crossed the border that December NWMP Inspector James Walsh rode out to meet them and offered them sanctuary in Canada as long as they lived in peace. Three months later another band crossed the border and Sitting Bull and his band followed that summer. All were given sanctuary in Canada.

Canada accepted these Sioux as refugees but would not make a treaty with them or give them a reservation. Basic essentials such as ammunition and flour were provided at first but soon tapered off and the Sioux were told they would have to fend for themselves while they lived in Canada. With the buffalo populations virtually non existent in Canada by this time Sioux hunters began sneaking across the border to hunt. They were chased back by the US Cavalry in 1880 and again in 1881. When General Miles approached the NWMP to make arrangements to meet with Sitting Bull and his primary chiefs he was refused as Inspector Walsh told him that the Sioux had no desire to speak with him.

Members of Canada's Blackfoot tribe had signed treaties and moved onto reservations by 1880. Their young craved adventure and wanted to go on horse stealing raids, but we're soon captured and prosecuted when they did so in Canada. Soon they realized that they were immune from persecution if they stole horses from the United States and made it safely back across the "Medicine Line". They continued to do so for many years, with their last large raid across the border made in 1898 according to LV Kelly.