Chicago Dems Plotted the World’s Greatest Jailbreak to Steal a Presidential Election

During the Civil War, Democrats came up with a unique plan to find more voters.

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“They will vote early and often, and they will fight,” Charles Walsh, a top figure in the Democratic political machine who had unsuccessfully run for Sheriff of Cook County, promised.

The year was 1864 and Walsh, the “doorkeeper’ of the Illinois House, who lost an election to a Republican by less than 800 votes, had a plan to win a presidential election the Chicago Way.

It was simple.

Abraham Lincoln was so associated with Illinois that “Land of Lincoln” would become its name, but Chicago was a whole other matter. Could Chicago Democrats hope to win Illinois? The Democrats had bet big on Chicago by bringing the Democratic National Convention to town.

The Democratic convention adopted a platform claiming that “after four years of failure to restore the Union by the experiment of war”, it was time to negotiate a settlement. But the convention was also to be the opening round of what became known as the “Chicago Conspiracy” in which Democrats plotted treason, a coup and a unique way to win an election.

Even by the standards of a time when urban Democrat political machines would bring in prisoners and lunatics to vote, often more than once, and even waylay passerby, get them drunk and force them to vote Democrat (a practice known as ‘cooping’ that some historians claim led to Edgar Allen Poe’s mysterious death), Walsh’s plan was ambitious.

Previously, the Chicago Tribune had reported that, “the mayor of Chicago… released nearly all the inmates of the bridewell on condition that they would vote for him today.” But the Bridewell prison held mere hundreds of inmates and what it would take was the world’s greatest jailbreak.

Chicago needed some good Democrats and the Cook County Democrat bigwig knew where to get them. At Camp Douglas on the South Side of Chicago, tens of thousands of Confederate prisoners of war housed in poor conditions and suffering from a high death toll, like most large camps on both sides, had become a popular cause for Chicago’s Democrat ‘Copperheads’.

While previous efforts had been made to help some Confederate prisoners escape, the Chicago Conspiracy had a much better idea. Why not break them loose and have them vote Democrat?

The story of the Chicago Conspiracy is part of the lost history retold in my book, ‘Domestic Enemies: The Founding Fathers’ Fight Against the Left’ which reveals the corrupt and violent origins of the American Left and the Democrats and what we can learn from that today.

Walsh’s plan may seem wild, but it was actually part of a nationwide Democrat conspiracy against the election featuring terrorism, race riots and simultaneous coups in major Northern cities that is retold in detail in ‘Domestic Enemies . In New York, local Democrats and Confederate agents had staged the Draft Riots, attacking black people and Republicans to seize power and then when that failed a campaign of domestic terrorism by attempting to set fire to Broadway hotels and theaters with thousands of people trapped inside.

But Chicago Democrats like Walsh were more practical. He stockpiled weapons, which his daughter would later claim were meant to be used “to protect Democrats at the polls.” These Democrat election defense weapons included “200 stands of arms, with all the necessary ammunition and two cart-loads of large revolvers, loaded and capped ready for use.”

The Democratic National Convention would provide a pretext for a large number of visitors to come to Chicago all at once. And Chicago’s proximity to Canada, where the real conspiracies were being hatched under British supervision by radicals too extreme for the Confederacy, like John Wilkes Booth, would make it a convenient jumping off point for changing history.

(The combination came together in Walsh’s fellow conspirator, Col. George St. Leger Grenfell, a British mercenary who lived with his own harem in a Muslim country before coming to America, being arrested and sentenced to death, having his sentence commuted through the intervention of the British government, and then managing to escape by boat and becoming a pirate.)

With enemy agents, likely from the Knights of the Golden Circle, the predecessors of the KKK, blending in with the arrivals to the Democratic National Convention, they would have plenty of time to coordinate with Walsh’s Democrat thugs “ready to shed blood”. Then they would liberate the tens of thousands of Confederates in Camp Douglas. And take them out to vote.

The plan was that “the rebels were to march into the city” and “take possession of the polls, voting in each precinct, and preventing the deposition in the ballot-box of any other than the McClellan ticket.” Such gangland voting tactics were not unusual in Tammany Hall and other Democrat urban political machines. Indeed one reason that was given for not allowing women to vote was that it was too violent due to Democrat gangs terrorizing anyone who voted differently.

But Chicago Democrats were thinking even bigger with the world’s greatest jailbreak by bringing in tens of thousands of heavily armed Confederate Democrats who would, in Walsh’s words “vote early and often, and they will fight.”

In typical Chicago fashion, Walsh linked fighting and voting together.

Then, in even more typical Chicago fashion, the Chicago and Confederate Democrats, after voting, would loot all the banks.

Unlike the Draft Riots, which at least succeeded in driving enough Republicans and black voters out of New York City so that the Tammany Hall machine was able to secure Democrat control of local elections, the Chicago Conspiracy, like the entire Northwest Conspiracy, failed badly.

The Democrat plan to either rig the 1864 election or, failing that, seize control of major cities and secede from the United States, fell apart. These conspiracies owed less to the South, where the Confederate leadership was less likely to entertain such madness, than to local Democrat political machines, like those of Tammany Hall and Cook County, and British agents who publicly opposed slavery, but covertly were thrilled to see America tearing itself apart.

(The unresolved hostilities from the British covert backing for the South would play out in the form of the Fenian raids into Canada and the threat of a potential third war with America that continued to linger long after the North and the South had bandaged the wounds of their war. And there was a good deal of irony in Canada harboring some of the Democrat radicals who had originally been among the most vocal proponents of invading and annexing Canada.)

While Democrats like Walsh appeared to be making a dangerous gamble in an era when men could still be shot for treason, they were only mildly inconvenienced by their conspiracies, unlike Southerners, many of whom suffered greatly during the war even when they opposed slavery.

Even right after Lincoln’s assassination, Walsh was only sentenced to five years in prison and was released much sooner so that he was out by 1865. Other prominent conspirators walked away entirely including a former Chicago mayor. So did the majority of the party thugs who proved the Democrats protected their own whether in the streets or in a court of law.

While the Chicago Conspiracy failed, it’s hard not to see it as a trial run for the modern party.

The original plan to “seize the polls” and “stuff the boxes sufficiently to secure the city, county and State” and then “to utterly sack the city, burning and destroying every description of property, except what they could appropriate for their own use” seems like just the basic strategy of what Democrats have done to Chicago, Illinois and the United States.

“God be praised. Chicago has redeemed herself,” the Chicago Tribune had celebrated the Republican victory in 1862 even though the Democrats had “flooded the wards with illegal voters and counterfeit tickets.” But it’s been a long time since Chicago has been redeemed.

The illegal voters are everywhere and Democrats have ushered in illegal invaders from all the nations of the world to march across the Southern border and stuff ballot boxes and loot cities.

What was once a Democrat conspiracy is now just Democrat policy.

[The full story of the Democratic plot to rig the 1864 election is told in the final chapter of my book, ‘Domestic Enemies: The Founding Fathers’ Fight Against the Left’.]