With Teddy Roosevelt grinding his axe for the radical left in America, mustache bristling with unbridled rage, it would only be fair to give Emma Goldman a mention as someone squarely in TR's crosshairs.
Anarchist, feminist, gay rights activist, and more, Emma Goldman was considered in her time one of the most dangerous women in America for peddling the deadly poison of free speech and politics that weren't generally liked. She was a fiery orator and was described by New York journalist Nellie Bly as a modern Joan of Arc (thankfully not because of any propensities for getting burned at the stake).
She believed that change could come rapidly, that the American government was so stagnant in pushing meaningful reform that trusting it to fix itself was the worst kind of naive. She famously said that, "if voting changed anything, it would be illegal," which sounds like a great line for a bumper sticker.
To Goldman, every citizen needed to be their own advocate and join together to replace the system with something that could work for them. She's TR's ideological flipside; the boogeyman he conjures up as a representation of evil in the world—fast, radical change that seeks to undo established order.
She was born in what would become modern-day Lithuania to parents locked in an unhappy marriage, facing poverty thanks to her father's terrible investments of her mother's inheritance. When relatives of hers decided to move to New York, she threatened to throw herself into the river if her father didn't let her go along.
Goldman was inspired by the labor movement, of workers trying to stand up to the brutal conditions that they toiled under. Ironically for someone who shifted gears to more of an activist role, she got her political start conspiring with her lover to assassinate Henry Clay Frick for how he broke up the Homestead Strike. After his "gun and a nice suit" plan went haywire, Emma spent some time in prison as a co-conspirator.
After her stint in the slammer, she honed her rough edges in Europe, getting a few degrees under her belt, and she scratched "attempted assassination" off her resume when she returned to United States as a formidable writer, journalist, and public speaker.
She and Teddy Roosevelt in particular shared some bad blood. Leon Czolgosz, the man who nixed McKinley and inadvertently made Roosevelt president, claimed to have gotten all of his inspiration for the deed from Emma Goldman herself.
In reality he was inspired by her in more of the creepy stalker way, but it was all the same to TR—Emma's politics led the man to violence, and in his mind there was no room for this shade of grey. She was brought in as a suspect, her house raided, and was detained for two weeks while people tried to glue her to the case. She'd eventually be let go, but at that point she was treading dangerous waters. Czolgosz's act was pretty much all people needed to tie the anarchist movement together with violence, and it quickly fell out of fashion.
As public attitude toward anarchism continued to curdle into the Red Scare of 1919, Emma Goldman was deported from the United States and sent back to a country she hadn't lived in since she was a girl. In the heart of Bolshevik Russia, what started as admiration turned into disgust for the brutal repressive nature of the Soviet Union.
It was a pretty quick honeymoon phase.
She was pretty much cut off from everyone at this point—she was too radical for the socialists and too liberal for the communists. Her disillusionment with Russia, however, warmed her relationship with America in that way only hating the Ruskies can do. Publish one book smack-talking Russia and you're pretty much guaranteed a lecture tour.
She returned to the US for a while to do just that for her memoirs and then spent the next twenty years involved in writing and activist work, all the way up until her death in 1940. Because life seems to have a flair for the ironic, her first stroke left her unable to talk, doing what people for decades had been trying to: silence her.
She died after the second stroke a few weeks later and was buried alongside other famous labor organizers in the outskirts of Chicago, finally returning to the city where she got her start.